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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014352

Secondary Accession Numbers

HMDB0001916
HMDB01916
HMDB14352

Metabolite Identification

Common Name

Azithromycin

Description

Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. It is used to treat certain bacterial infections, most often bacteria causing middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia, and sinusitis. It is also effective against certain sexually transmitted infectious diseases, such as non-gonococcal urethritis and cervicitis. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half-life, which enables once-daily dosing, and shorter administration durations is a property distinct from other macrolides. Azithromycin is derived from erythromycin; however, it differs chemically from erythromycin in that a methyl-substituted nitrogen atom is incorporated into the lactone ring, thus making the lactone ring 15-membered. Azithromycin is sold under the brand names Zithromax ("Zmax") and Sumamed, and is one of the world's best-selling antibiotics.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305201902232D          

 52 54  0  0  0  0            999 V2000
   -3.2657    2.7280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7679    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6782    2.0135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3554    1.9962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7679    1.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    0.6984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1845   -0.1266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7679   -0.7100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7679   -1.5350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4823   -1.9475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1968   -1.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -0.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -0.2975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9113    0.5275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3279    1.1109    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2657    3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4751    2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258    0.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4823   -2.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876    0.9119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5585    2.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258    0.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -3.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612   -0.6851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -1.9475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -4.0318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7987   -1.3996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9737   -1.3996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5612   -2.1141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -2.8286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7986   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112   -2.1141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1856   -4.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519   -4.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395   -5.4608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1855   -5.4608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5981   -4.7463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3820   -0.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2228   -6.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -2.1141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -4.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5980   -6.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064   -4.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -1.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4824   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15  3  1  0  0  0  0
  1 16  1  0  0  0  0
  3 17  1  1  0  0  0
 15 18  1  1  0  0  0
 14 19  1  1  0  0  0
 10 20  1  1  0  0  0
  6 21  1  1  0  0  0
  4 22  1  6  0  0  0
  6 23  1  6  0  0  0
 14 24  1  6  0  0  0
 13 25  1  6  0  0  0
  9 26  1  6  0  0  0
  7 27  1  6  0  0  0
 11 28  2  0  0  0  0
 25 29  1  0  0  0  0
 32 27  1  1  0  0  0
 30 26  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 37 30  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 41  1  0  0  0  0
 31 42  1  6  0  0  0
 39 43  1  6  0  0  0
 41 44  1  6  0  0  0
 34 45  1  1  0  0  0
 36 46  1  1  0  0  0
 41 47  1  1  0  0  0
 40 48  1  1  0  0  0
 47 49  1  0  0  0  0
 46 50  1  0  0  0  0
 46 51  1  0  0  0  0
  8 52  1  6  0  0  0
M  END

HMDB0014352
     RDKit          3D
Azithromycin
124126  0  0  0  0  0  0  0  0999 V2000
   -4.8658   -0.9288    1.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8977   -2.0368    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0504   -1.6357   -0.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7174   -1.4094   -0.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673   -0.3201    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622   -0.2977    1.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.8715   -0.5116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2183    0.7903   -1.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5093    1.5850   -0.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8874    2.6421    0.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    3.8707    0.0634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4070    4.4802    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    5.7686    1.0321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7815    6.2803    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    5.3945    2.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    6.3634    3.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    6.6900    0.2234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4579    7.9184    0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165    5.9986    0.1937 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4832    5.9706   -1.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923    4.7385    0.7676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004    0.9892    0.2040 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5315    2.2311    0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786    0.1437   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5764   -0.3385    0.4525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.1024    0.6626 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5130   -1.3056    0.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688   -1.0133    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6102   -2.0286   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4406   -0.8660    1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857   -0.7098    2.5963 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8709   -1.8093    3.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9574   -2.4294    4.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158   -2.8192    2.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.1833    2.0799 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7852    1.4944    2.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.8195   -1.5098 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7715   -1.1467   -2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8072   -0.1095   -2.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -2.0347   -1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8334   -3.1691   -0.5927 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3748   -3.0230    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -4.3197   -1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -3.6954   -1.7643 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2456   -4.1067   -3.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -4.0871   -1.1304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3430   -5.6200   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -3.7493   -1.9041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5896   -4.7746   -1.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226   -2.4755   -1.7104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8566   -2.6723   -1.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943   -1.6838   -2.8651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4388   -0.0025    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168   -1.1844    2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8777   -0.7360    2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9265   -2.2524    0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3833   -2.8993    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4691   -0.6075   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238    1.5624   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6346    1.5613   -2.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2804    0.9159   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -0.1892   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    2.1358   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742    3.9763   -1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277    4.7980   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1267    3.8343    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958    7.1897    1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4348    5.4515    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    6.5522    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2838    5.8433    4.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9017    7.1005    2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6397    6.8415    3.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9217    6.7344   -0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    8.4706    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5747    6.5866    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431    6.9078   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    5.1416   -1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    5.7784   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    0.5240    1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.9318   -0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    2.6039    1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    2.0254    0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    0.8914   -1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857    0.6318    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995   -0.0479   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4756   -2.3863   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9580   -2.9179   -0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366   -1.5971   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292    0.1040    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2252   -1.6130    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8904   -0.0504    3.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7007   -2.8420    3.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848   -3.3262    4.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -1.7401    4.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -3.5794    3.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -3.4560    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.4334    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    0.1150    2.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0971    2.0829    2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408   -2.1481   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433   -1.3041   -3.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4779   -0.3247   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    0.6839   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -2.4767   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288   -1.8035   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -3.5903   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -3.9756    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -2.7785    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -2.2819    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -4.9493   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -4.9004   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196   -5.0398   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -3.3186   -3.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2080   -4.3772   -3.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -3.7481   -0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -5.9420    0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -6.0439   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725   -6.1158   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4245   -3.9392   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7097   -4.8507   -0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1731   -3.5392   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1363   -2.8881   -2.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3631   -1.7307   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359   -0.9161   -2.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
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 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
  9 22  1  0
 22 23  1  0
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 50  3  1  0
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 31 91  1  1
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 38100  1  0
 38101  1  0
 38102  1  0
 39103  1  0
 40104  1  0
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 41106  1  1
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 43110  1  0
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 48119  1  6
 49120  1  0
 51121  1  0
 51122  1  0
 51123  1  0
 52124  1  0
M  END


  Mrv1652305201902232D          

 52 54  0  0  0  0            999 V2000
   -3.2657    2.7280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7679    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6782    2.0135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3554    1.9962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7679    1.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    0.6984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1845   -0.1266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7679   -0.7100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7679   -1.5350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4823   -1.9475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1968   -1.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -0.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -0.2975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9113    0.5275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3279    1.1109    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2657    3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4751    2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258    0.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4823   -2.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876    0.9119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5585    2.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258    0.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -3.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612   -0.6851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -1.9475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -4.0318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7987   -1.3996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9737   -1.3996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5612   -2.1141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -2.8286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7986   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112   -2.1141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1856   -4.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519   -4.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395   -5.4608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1855   -5.4608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5981   -4.7463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3820   -0.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2228   -6.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -2.1141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -4.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5980   -6.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064   -4.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -1.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4824   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15  3  1  0  0  0  0
  1 16  1  0  0  0  0
  3 17  1  1  0  0  0
 15 18  1  1  0  0  0
 14 19  1  1  0  0  0
 10 20  1  1  0  0  0
  6 21  1  1  0  0  0
  4 22  1  6  0  0  0
  6 23  1  6  0  0  0
 14 24  1  6  0  0  0
 13 25  1  6  0  0  0
  9 26  1  6  0  0  0
  7 27  1  6  0  0  0
 11 28  2  0  0  0  0
 25 29  1  0  0  0  0
 32 27  1  1  0  0  0
 30 26  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 37 30  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 41  1  0  0  0  0
 31 42  1  6  0  0  0
 39 43  1  6  0  0  0
 41 44  1  6  0  0  0
 34 45  1  1  0  0  0
 36 46  1  1  0  0  0
 41 47  1  1  0  0  0
 40 48  1  1  0  0  0
 47 49  1  0  0  0  0
 46 50  1  0  0  0  0
 46 51  1  0  0  0  0
  8 52  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0014352

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

> <INCHI_KEY>
MQTOSJVFKKJCRP-BICOPXKESA-N

> <FORMULA>
C38H72N2O12

> <MOLECULAR_WEIGHT>
748.9845

> <EXACT_MASS>
748.508525778

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
124

> <JCHEM_AVERAGE_POLARIZABILITY>
82.92978743941553

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.4447815993333313

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.89815406880848

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.428323628576404

> <JCHEM_PKA_STRONGEST_BASIC>
9.569664875084948

> <JCHEM_POLAR_SURFACE_AREA>
180.08

> <JCHEM_REFRACTIVITY>
194.1082

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azithromycin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014352
     RDKit          3D
Azithromycin
124126  0  0  0  0  0  0  0  0999 V2000
   -4.8658   -0.9288    1.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8977   -2.0368    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0504   -1.6357   -0.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7174   -1.4094   -0.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673   -0.3201    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622   -0.2977    1.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.8715   -0.5116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2183    0.7903   -1.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5093    1.5850   -0.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8874    2.6421    0.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    3.8707    0.0634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4070    4.4802    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    5.7686    1.0321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7815    6.2803    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    5.3945    2.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    6.3634    3.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    6.6900    0.2234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4579    7.9184    0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165    5.9986    0.1937 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4832    5.9706   -1.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923    4.7385    0.7676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004    0.9892    0.2040 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5315    2.2311    0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786    0.1437   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5764   -0.3385    0.4525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.1024    0.6626 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5130   -1.3056    0.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688   -1.0133    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6102   -2.0286   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4406   -0.8660    1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857   -0.7098    2.5963 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8709   -1.8093    3.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9574   -2.4294    4.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158   -2.8192    2.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.1833    2.0799 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7852    1.4944    2.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.8195   -1.5098 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7715   -1.1467   -2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8072   -0.1095   -2.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -2.0347   -1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8334   -3.1691   -0.5927 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3748   -3.0230    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -4.3197   -1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -3.6954   -1.7643 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2456   -4.1067   -3.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -4.0871   -1.1304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3430   -5.6200   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -3.7493   -1.9041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5896   -4.7746   -1.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0366   -1.5971   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292    0.1040    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2252   -1.6130    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8904   -0.0504    3.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7007   -2.8420    3.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848   -3.3262    4.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -1.7401    4.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -3.5794    3.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -3.4560    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.4334    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    0.1150    2.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0971    2.0829    2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408   -2.1481   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433   -1.3041   -3.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4779   -0.3247   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    0.6839   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -2.4767   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288   -1.8035   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -3.5903   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -3.9756    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -2.7785    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -2.2819    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -4.9493   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -4.9004   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196   -5.0398   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -3.3186   -3.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1731   -3.5392   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3631   -1.7307   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359   -0.9161   -2.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  N   UNK     0      -6.096   5.092   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.300   5.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.866   3.759   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.530   3.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.300   2.393   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.211   1.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.211  -0.236   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.300  -1.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.300  -2.865   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.634  -3.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.967  -2.865   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.967  -1.325   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -7.301  -0.555   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.301   0.985   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.212   2.074   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.096   6.632   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.354   4.157   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.725   1.675   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.635   1.755   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.634  -5.175   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.724   1.702   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.043   4.125   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.877   0.534   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.635   0.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.635  -1.325   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.194  -5.986   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.048  -1.279   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -7.301  -3.635   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -10.175  -1.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.194  -7.526   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.358  -2.613   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.818  -2.613   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.048  -3.946   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.817  -5.280   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.357  -5.280   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.128  -3.946   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.346  -7.526   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.964  -8.860   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.194 -10.193   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.346 -10.193   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.116  -8.860   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.446  -1.524   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.283 -11.282   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.205  -9.949   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.047  -6.614   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0       5.668  -3.946   0.000  0.00  0.00           N+0
HETATM   47  O   UNK     0       2.205  -7.771   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       1.116 -11.527   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       3.745  -7.771   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.756  -2.857   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.438  -5.280   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -4.634  -0.555   0.000  0.00  0.00           C+0
CONECT    1    2    3   16                                                  
CONECT    2    1    4                                                       
CONECT    3    1   15   17                                                  
CONECT    4    2    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21   23                                             
CONECT    7    6    8   27                                                  
CONECT    8    7    9   52                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   19   24                                             
CONECT   15   14    3   18                                                  
CONECT   16    1                                                            
CONECT   17    3                                                            
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20   10                                                            
CONECT   21    6                                                            
CONECT   22    4                                                            
CONECT   23    6                                                            
CONECT   24   14                                                            
CONECT   25   13   29                                                       
CONECT   26    9   30                                                       
CONECT   27    7   32                                                       
CONECT   28   11                                                            
CONECT   29   25                                                            
CONECT   30   26   37   38                                                  
CONECT   31   32   36   42                                                  
CONECT   32   27   31   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   45                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31   46                                                  
CONECT   37   30   41                                                       
CONECT   38   30   39                                                       
CONECT   39   38   40   43                                                  
CONECT   40   39   41   48                                                  
CONECT   41   40   37   44   47                                             
CONECT   42   31                                                            
CONECT   43   39                                                            
CONECT   44   41                                                            
CONECT   45   34                                                            
CONECT   46   36   50   51                                                  
CONECT   47   41   49                                                       
CONECT   48   40                                                            
CONECT   49   47                                                            
CONECT   50   46                                                            
CONECT   51   46                                                            
CONECT   52    8                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

COMPND    HMDB0014352
HETATM    1  C1  UNL     1      -4.866  -0.929   1.737  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.898  -2.037   0.683  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.050  -1.636  -0.526  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.717  -1.409  -0.200  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.067  -0.320   0.302  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.662  -0.298   1.525  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.796   0.872  -0.512  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.218   0.790  -1.955  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.509   1.585  -0.288  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.887   2.642   0.589  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.014   3.871   0.063  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.407   4.480   0.186  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.378   5.769   1.032  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.781   6.280   1.085  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.857   5.394   2.239  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.718   6.363   3.190  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.455   6.690   0.223  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.458   7.918   0.833  1.00  0.00           O  
HETATM   19  C14 UNL     1      -0.116   5.999   0.194  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.483   5.971  -1.192  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.192   4.738   0.768  1.00  0.00           O  
HETATM   22  C16 UNL     1       0.700   0.989   0.204  1.00  0.00           C  
HETATM   23  C17 UNL     1       1.532   2.231   0.651  1.00  0.00           C  
HETATM   24  C18 UNL     1       1.679   0.144  -0.446  1.00  0.00           C  
HETATM   25  O7  UNL     1       2.576  -0.339   0.452  1.00  0.00           O  
HETATM   26  C19 UNL     1       3.827  -0.102   0.663  1.00  0.00           C  
HETATM   27  O8  UNL     1       4.513  -1.306   0.305  1.00  0.00           O  
HETATM   28  C20 UNL     1       5.869  -1.013   0.208  1.00  0.00           C  
HETATM   29  C21 UNL     1       6.610  -2.029  -0.636  1.00  0.00           C  
HETATM   30  C22 UNL     1       6.441  -0.866   1.575  1.00  0.00           C  
HETATM   31  C23 UNL     1       5.386  -0.710   2.596  1.00  0.00           C  
HETATM   32  N1  UNL     1       4.871  -1.809   3.269  1.00  0.00           N  
HETATM   33  C24 UNL     1       5.957  -2.429   4.054  1.00  0.00           C  
HETATM   34  C25 UNL     1       4.116  -2.819   2.707  1.00  0.00           C  
HETATM   35  C26 UNL     1       4.296   0.183   2.080  1.00  0.00           C  
HETATM   36  O9  UNL     1       4.785   1.494   2.185  1.00  0.00           O  
HETATM   37  C27 UNL     1       1.426  -0.820  -1.510  1.00  0.00           C  
HETATM   38  C28 UNL     1       2.771  -1.147  -2.188  1.00  0.00           C  
HETATM   39  O10 UNL     1       0.807  -0.109  -2.621  1.00  0.00           O  
HETATM   40  C29 UNL     1       0.672  -2.035  -1.480  1.00  0.00           C  
HETATM   41  C30 UNL     1       0.833  -3.169  -0.593  1.00  0.00           C  
HETATM   42  C31 UNL     1       0.375  -3.023   0.842  1.00  0.00           C  
HETATM   43  C32 UNL     1      -0.035  -4.320  -1.129  1.00  0.00           C  
HETATM   44  N2  UNL     1      -1.202  -3.695  -1.764  1.00  0.00           N  
HETATM   45  C33 UNL     1      -1.246  -4.107  -3.167  1.00  0.00           C  
HETATM   46  C34 UNL     1      -2.428  -4.087  -1.130  1.00  0.00           C  
HETATM   47  C35 UNL     1      -2.343  -5.620  -1.011  1.00  0.00           C  
HETATM   48  C36 UNL     1      -3.629  -3.749  -1.904  1.00  0.00           C  
HETATM   49  O11 UNL     1      -4.590  -4.775  -1.620  1.00  0.00           O  
HETATM   50  C37 UNL     1      -4.323  -2.476  -1.710  1.00  0.00           C  
HETATM   51  C38 UNL     1      -5.857  -2.672  -1.743  1.00  0.00           C  
HETATM   52  O12 UNL     1      -4.094  -1.684  -2.865  1.00  0.00           O  
HETATM   53  H1  UNL     1      -4.439  -0.002   1.253  1.00  0.00           H  
HETATM   54  H2  UNL     1      -4.217  -1.184   2.599  1.00  0.00           H  
HETATM   55  H3  UNL     1      -5.878  -0.736   2.131  1.00  0.00           H  
HETATM   56  H4  UNL     1      -5.926  -2.252   0.412  1.00  0.00           H  
HETATM   57  H5  UNL     1      -4.383  -2.899   1.152  1.00  0.00           H  
HETATM   58  H6  UNL     1      -4.469  -0.607  -0.787  1.00  0.00           H  
HETATM   59  H7  UNL     1      -2.624   1.562  -0.127  1.00  0.00           H  
HETATM   60  H8  UNL     1      -1.635   1.561  -2.536  1.00  0.00           H  
HETATM   61  H9  UNL     1      -3.280   0.916  -2.155  1.00  0.00           H  
HETATM   62  H10 UNL     1      -1.906  -0.189  -2.353  1.00  0.00           H  
HETATM   63  H11 UNL     1      -0.334   2.136  -1.260  1.00  0.00           H  
HETATM   64  H12 UNL     1      -0.774   3.976  -1.008  1.00  0.00           H  
HETATM   65  H13 UNL     1      -2.828   4.798  -0.790  1.00  0.00           H  
HETATM   66  H14 UNL     1      -3.127   3.834   0.666  1.00  0.00           H  
HETATM   67  H15 UNL     1      -3.896   7.190   1.703  1.00  0.00           H  
HETATM   68  H16 UNL     1      -4.435   5.451   1.412  1.00  0.00           H  
HETATM   69  H17 UNL     1      -4.087   6.552   0.053  1.00  0.00           H  
HETATM   70  H18 UNL     1      -1.284   5.843   4.099  1.00  0.00           H  
HETATM   71  H19 UNL     1      -0.902   7.100   2.929  1.00  0.00           H  
HETATM   72  H20 UNL     1      -2.640   6.842   3.514  1.00  0.00           H  
HETATM   73  H21 UNL     1      -1.922   6.734  -0.790  1.00  0.00           H  
HETATM   74  H22 UNL     1      -2.177   8.471   0.442  1.00  0.00           H  
HETATM   75  H23 UNL     1       0.575   6.587   0.828  1.00  0.00           H  
HETATM   76  H24 UNL     1       1.043   6.908  -1.396  1.00  0.00           H  
HETATM   77  H25 UNL     1       1.206   5.142  -1.228  1.00  0.00           H  
HETATM   78  H26 UNL     1      -0.279   5.778  -1.974  1.00  0.00           H  
HETATM   79  H27 UNL     1       0.473   0.524   1.216  1.00  0.00           H  
HETATM   80  H28 UNL     1       1.483   2.932  -0.231  1.00  0.00           H  
HETATM   81  H29 UNL     1       1.219   2.604   1.596  1.00  0.00           H  
HETATM   82  H30 UNL     1       2.612   2.025   0.698  1.00  0.00           H  
HETATM   83  H31 UNL     1       2.346   0.891  -1.015  1.00  0.00           H  
HETATM   84  H32 UNL     1       4.386   0.632   0.033  1.00  0.00           H  
HETATM   85  H33 UNL     1       5.900  -0.048  -0.383  1.00  0.00           H  
HETATM   86  H34 UNL     1       7.476  -2.386  -0.017  1.00  0.00           H  
HETATM   87  H35 UNL     1       5.958  -2.918  -0.854  1.00  0.00           H  
HETATM   88  H36 UNL     1       7.037  -1.597  -1.552  1.00  0.00           H  
HETATM   89  H37 UNL     1       7.029   0.104   1.545  1.00  0.00           H  
HETATM   90  H38 UNL     1       7.225  -1.613   1.815  1.00  0.00           H  
HETATM   91  H39 UNL     1       5.890  -0.050   3.418  1.00  0.00           H  
HETATM   92  H40 UNL     1       6.701  -2.842   3.344  1.00  0.00           H  
HETATM   93  H41 UNL     1       5.485  -3.326   4.523  1.00  0.00           H  
HETATM   94  H42 UNL     1       6.394  -1.740   4.777  1.00  0.00           H  
HETATM   95  H43 UNL     1       3.796  -3.579   3.500  1.00  0.00           H  
HETATM   96  H44 UNL     1       4.543  -3.456   1.916  1.00  0.00           H  
HETATM   97  H45 UNL     1       3.145  -2.433   2.340  1.00  0.00           H  
HETATM   98  H46 UNL     1       3.455   0.115   2.811  1.00  0.00           H  
HETATM   99  H47 UNL     1       4.097   2.083   2.569  1.00  0.00           H  
HETATM  100  H48 UNL     1       3.141  -2.148  -1.849  1.00  0.00           H  
HETATM  101  H49 UNL     1       2.643  -1.304  -3.294  1.00  0.00           H  
HETATM  102  H50 UNL     1       3.478  -0.325  -1.996  1.00  0.00           H  
HETATM  103  H51 UNL     1       1.373   0.684  -2.812  1.00  0.00           H  
HETATM  104  H52 UNL     1       0.783  -2.477  -2.548  1.00  0.00           H  
HETATM  105  H53 UNL     1      -0.429  -1.803  -1.525  1.00  0.00           H  
HETATM  106  H54 UNL     1       1.891  -3.590  -0.613  1.00  0.00           H  
HETATM  107  H55 UNL     1       0.616  -3.976   1.420  1.00  0.00           H  
HETATM  108  H56 UNL     1      -0.682  -2.779   0.916  1.00  0.00           H  
HETATM  109  H57 UNL     1       1.035  -2.282   1.327  1.00  0.00           H  
HETATM  110  H58 UNL     1      -0.386  -4.949  -0.305  1.00  0.00           H  
HETATM  111  H59 UNL     1       0.550  -4.900  -1.873  1.00  0.00           H  
HETATM  112  H60 UNL     1      -1.820  -5.040  -3.329  1.00  0.00           H  
HETATM  113  H61 UNL     1      -1.692  -3.319  -3.795  1.00  0.00           H  
HETATM  114  H62 UNL     1      -0.208  -4.377  -3.541  1.00  0.00           H  
HETATM  115  H63 UNL     1      -2.539  -3.748  -0.084  1.00  0.00           H  
HETATM  116  H64 UNL     1      -2.187  -5.942   0.044  1.00  0.00           H  
HETATM  117  H65 UNL     1      -1.516  -6.044  -1.587  1.00  0.00           H  
HETATM  118  H66 UNL     1      -3.273  -6.116  -1.340  1.00  0.00           H  
HETATM  119  H67 UNL     1      -3.424  -3.939  -3.002  1.00  0.00           H  
HETATM  120  H68 UNL     1      -4.710  -4.851  -0.628  1.00  0.00           H  
HETATM  121  H69 UNL     1      -6.173  -3.539  -1.168  1.00  0.00           H  
HETATM  122  H70 UNL     1      -6.136  -2.888  -2.816  1.00  0.00           H  
HETATM  123  H71 UNL     1      -6.363  -1.731  -1.501  1.00  0.00           H  
HETATM  124  H72 UNL     1      -4.736  -0.916  -2.764  1.00  0.00           H  
CONECT    1    2   53   54   55
CONECT    2    3   56   57
CONECT    3    4   50   58
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    9   59
CONECT    8   60   61   62
CONECT    9   10   22   63
CONECT   10   11
CONECT   11   12   21   64
CONECT   12   13   65   66
CONECT   13   14   15   17
CONECT   14   67   68   69
CONECT   15   16
CONECT   16   70   71   72
CONECT   17   18   19   73
CONECT   18   74
CONECT   19   20   21   75
CONECT   20   76   77   78
CONECT   22   23   24   79
CONECT   23   80   81   82
CONECT   24   25   37   83
CONECT   25   26
CONECT   26   27   35   84
CONECT   27   28
CONECT   28   29   30   85
CONECT   29   86   87   88
CONECT   30   31   89   90
CONECT   31   32   35   91
CONECT   32   33   34
CONECT   33   92   93   94
CONECT   34   95   96   97
CONECT   35   36   98
CONECT   36   99
CONECT   37   38   39   40
CONECT   38  100  101  102
CONECT   39  103
CONECT   40   41  104  105
CONECT   41   42   43  106
CONECT   42  107  108  109
CONECT   43   44  110  111
CONECT   44   45   46
CONECT   45  112  113  114
CONECT   46   47   48  115
CONECT   47  116  117  118
CONECT   48   49   50  119
CONECT   49  120
CONECT   50   51   52
CONECT   51  121  122  123
CONECT   52  124
END

HMDB0014352
     RDKit          3D
Azithromycin
124126  0  0  0  0  0  0  0  0999 V2000
   -4.8658   -0.9288    1.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8977   -2.0368    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0504   -1.6357   -0.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7174   -1.4094   -0.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673   -0.3201    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622   -0.2977    1.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.8715   -0.5116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2183    0.7903   -1.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5093    1.5850   -0.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8874    2.6421    0.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    3.8707    0.0634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4070    4.4802    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    5.7686    1.0321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7815    6.2803    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    5.3945    2.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    6.3634    3.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    6.6900    0.2234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4579    7.9184    0.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165    5.9986    0.1937 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4832    5.9706   -1.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923    4.7385    0.7676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004    0.9892    0.2040 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5315    2.2311    0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786    0.1437   -0.4457 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5764   -0.3385    0.4525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.1024    0.6626 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5130   -1.3056    0.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688   -1.0133    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6102   -2.0286   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4406   -0.8660    1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857   -0.7098    2.5963 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8709   -1.8093    3.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9574   -2.4294    4.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158   -2.8192    2.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960    0.1833    2.0799 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7852    1.4944    2.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.8195   -1.5098 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7715   -1.1467   -2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8072   -0.1095   -2.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -2.0347   -1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8334   -3.1691   -0.5927 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3748   -3.0230    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -4.3197   -1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -3.6954   -1.7643 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2456   -4.1067   -3.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -4.0871   -1.1304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3430   -5.6200   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291   -3.7493   -1.9041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5896   -4.7746   -1.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226   -2.4755   -1.7104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8566   -2.6723   -1.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943   -1.6838   -2.8651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4388   -0.0025    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168   -1.1844    2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8777   -0.7360    2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9265   -2.2524    0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3833   -2.8993    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4691   -0.6075   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238    1.5624   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6346    1.5613   -2.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2804    0.9159   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -0.1892   -2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    2.1358   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7742    3.9763   -1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277    4.7980   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1267    3.8343    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958    7.1897    1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4348    5.4515    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    6.5522    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2838    5.8433    4.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9017    7.1005    2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6397    6.8415    3.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9217    6.7344   -0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    8.4706    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5747    6.5866    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431    6.9078   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    5.1416   -1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    5.7784   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730    0.5240    1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.9318   -0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    2.6039    1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    2.0254    0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    0.8914   -1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857    0.6318    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995   -0.0479   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4756   -2.3863   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9580   -2.9179   -0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366   -1.5971   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292    0.1040    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2252   -1.6130    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8904   -0.0504    3.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7007   -2.8420    3.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848   -3.3262    4.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -1.7401    4.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -3.5794    3.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -3.4560    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452   -2.4334    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    0.1150    2.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0971    2.0829    2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408   -2.1481   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433   -1.3041   -3.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4779   -0.3247   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    0.6839   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -2.4767   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288   -1.8035   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -3.5903   -0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -3.9756    1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -2.7785    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -2.2819    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -4.9493   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -4.9004   -1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196   -5.0398   -3.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -3.3186   -3.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2080   -4.3772   -3.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -3.7481   -0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -5.9420    0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -6.0439   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725   -6.1158   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4245   -3.9392   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7097   -4.8507   -0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1731   -3.5392   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1363   -2.8881   -2.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3631   -1.7307   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359   -0.9161   -2.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 52124  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one	ChEBI
Azenil	ChEBI
Azifast	ChEBI
Azigram	ChEBI
Azimakrol	ChEBI
Azithromycine	ChEBI
Azithromycinum	ChEBI
Azitromicina	ChEBI
Azitromin	ChEBI
Hemomycin	ChEBI
Zithromax	ChEBI
Zmax	ChEBI
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one	Generator
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one	Generator
Azithramycine	HMDB
Azithromycin dihydrate	HMDB
Azythromycin	HMDB
Dihydrate, azithromycin	HMDB
Monohydrate, azithromycin	HMDB
Pfizer brand OF azithromycin	HMDB
Azadose	HMDB
Azitrocin	HMDB
Funk brand OF azithromycin dihydrate	HMDB
Pharmacia brand OF azithromycin dihydrate	HMDB
Sumamed	HMDB
Zentavion	HMDB
Azithromycin monohydrate	HMDB
Azithromycin pfizer brand	HMDB
Goxal	HMDB
Mack brand OF azithromycin dihydrate	HMDB
Toraseptol	HMDB
Bayer brand OF azithromycin dihydrate	HMDB
Lesvi brand OF azithromycin dihydrate	HMDB
Pfizer brand OF azithromycin dihydrate	HMDB
Ultreon	HMDB
Vinzam	HMDB
Vita brand OF azithromycin dihydrate	HMDB
Zitromax	HMDB

Chemical Formula

C₃₈H₇₂N₂O₁₂

Average Molecular Weight

748.9845

Monoisotopic Molecular Weight

748.508525778

IUPAC Name

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Traditional Name

azithromycin

CAS Registry Number

83905-01-5

SMILES

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O

InChI Identifier

InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

InChI Key

MQTOSJVFKKJCRP-BICOPXKESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Azacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organopnictogen compound
Amine
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

macrolide antibiotic (CHEBI:2955 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Exogenous

Exogenous (HMDB: HMDB0014352)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Azithromycin Action Pathway (PathBank: SMP0000247)

Role

Industrial application

Drug (HMDB: HMDB0014352)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	113 - 115 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.51 g/L	Not Available
LogP	4.02	MCFARLAND,JW ET AL. (1997)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	263.507	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001324

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.44	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.43	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	194.11 m³·mol⁻¹	ChemAxon
Polarizability	82.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	265.709	30932474
DeepCCS	[M-H]-	263.986	30932474
DeepCCS	[M-2H]-	298.018	30932474
DeepCCS	[M+Na]+	272.001	30932474
AllCCS	[M+H]+	267.5	32859911
AllCCS	[M+H-H2O]+	267.2	32859911
AllCCS	[M+NH4]+	267.6	32859911
AllCCS	[M+Na]+	267.7	32859911
AllCCS	[M-H]-	253.8	32859911
AllCCS	[M+Na-2H]-	259.3	32859911
AllCCS	[M+HCOO]-	265.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	3.62 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8197 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	360.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1177.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	141.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	98.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	418.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	861.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	824.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	184.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	700.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	256.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	695.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azithromycin	CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O	3444.3	Standard polar	33892256
Azithromycin	CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O	4319.7	Standard non polar	33892256
Azithromycin	CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O	4369.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Azithromycin Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00207	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00207	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00207

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10482163

KEGG Compound ID

C06838

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azithromycin

METLIN ID

Not Available

PubChem Compound

447043

PDB ID

ZIT

ChEBI ID

2955

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [PubMed:17051490 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742 ]
Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. [PubMed:14744620 ]

Showing metabocard for Azithromycin (HMDB0014352)

MOL for HMDB0014352 (Azithromycin)

3D MOL for HMDB0014352 (Azithromycin)

3D SDF for HMDB0014352 (Azithromycin)

3D-SDF for HMDB0014352 (Azithromycin)

PDB for HMDB0014352 (Azithromycin)

3D PDB for HMDB0014352 (Azithromycin)

SMILES for HMDB0014352 (Azithromycin)

INCHI for HMDB0014352 (Azithromycin)

Structure for HMDB0014352 (Azithromycin)

3D Structure for HMDB0014352 (Azithromycin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes

References

References

Transporters

References