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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-16 12:27:59 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005007

Secondary Accession Numbers

HMDB0014779
HMDB05007
HMDB14779

Metabolite Identification

Common Name

Simvastatin

Description

Simvastatin is a hypolipidemic drug belonging to the class of pharmaceuticals called 'statins'. It is used to control hypercholesterolemia (elevated cholesterol levels) and to prevent cardiovascular disease. Simvastatin is a synthetic derivate of a fermentation product of Aspergillus terreus; Simvastatin is a powerful lipid-lowering drug that can decrease low density lipoprotein (LDL) levels by up to 50 percent. It is used in doses of 5 mg up to 80 mg. Higher doses (160 mg) have been found to be too toxic, while giving only minimal benefit in terms of lipid lowering. There is no real effect on HDL and triglyceride levels. Simvastatin (INN) is a hypolipidemic drug belonging to the class of pharmaceuticals called 'statins'. It is used to control hypercholesterolemia (elevated cholesterol levels) and to prevent cardiovascular disease. Simvastatin is a synthetic derivate of a fermentation product of Aspergillus terreus; The drug is the form of an inactive lactone that is hydrolized after ingestion to produce the active agent. It is a white, nonhygroscopic, crystalline powder that is practically insoluble in water, and freely soluble in chloroform, methanol and ethanol; Ezetimibe/simvastatin is a combination product to lower lipids and marketed as Vytorin.

Structure

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


  Mrv0541 04191212132D          

 31 33  0  0  1  0            999 V2000
   -0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447   -0.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    1.3303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    2.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    2.8693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1525    3.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    4.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370    4.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572    4.0872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7633    3.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    4.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    4.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    2.8866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311    2.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600    2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    1.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    0.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448    1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    0.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  6  0  0  0
  2  1  1  0  0  0  0
  2 13  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4 11  1  1  0  0  0
  1  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8 14  1  1  0  0  0
  7  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 12  1  6  0  0  0
  8 10  1  0  0  0  0
  6 10  2  0  0  0  0
 11 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  1  0  0  0
 24 25  2  0  0  0  0
 25 30  1  0  0  0  0
 25 26  1  0  0  0  0
 30 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0005007
     RDKit          3D
Simvastatin
 68 70  0  0  0  0  0  0  0  0999 V2000
   -3.2088    3.0117   -1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2042    1.8740   -1.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    0.5336   -1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    0.5238   -3.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5733   -0.5145   -2.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915    0.3202   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    1.1964    0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593   -0.8098   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -1.0834    0.9735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3024   -2.2877    1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1746   -3.4947    0.7238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3664   -3.6969   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -3.6284   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0098   -2.7307    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326   -2.9325   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -2.1642   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118   -1.0627    0.4121 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3823   -1.7263    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.4800    0.3832 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6732    0.8301    1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768    2.0103    0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411    2.0935    0.4175 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5428    1.9639    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    2.2288    1.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7532    1.0464    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    2.7758    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4383    3.8281   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    4.9817   -0.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978    3.5161    0.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1139   -1.5415    0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1806    2.6991   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5302    3.8892   -2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620    3.3068   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6386    2.0207   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958    1.9564   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -0.4805   -3.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    1.1946   -3.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412    0.9166   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8772   -0.9917   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037   -1.3240   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576   -0.0707   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555   -0.3056    1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3717   -1.9702    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -2.4206    2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2117   -4.3853    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167   -3.6383    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2756   -4.7410   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2748   -3.0105   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8331   -4.4947   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2264   -3.7377   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573   -2.3271   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586   -0.4413    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870   -2.7393    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9390   -1.1318    2.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.7950    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -0.3496   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9758    0.8028    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.1398    1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625    2.9738    0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899    2.1467   -0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    1.5850   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    2.6497    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.9476    2.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2919    2.9968    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2692    1.1329    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4209    3.2603    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    1.9882   -0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -1.8335    1.8923 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 19 30  1  0
 30  9  1  0
 30 14  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  1
 10 43  1  0
 10 44  1  0
 11 45  1  1
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  6
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 23 63  1  0
 24 64  1  1
 25 65  1  0
 26 66  1  0
 26 67  1  0
 30 68  1  1
M  END


  Mrv0541 04191212132D          

 31 33  0  0  1  0            999 V2000
   -0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1447   -0.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    1.3303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    2.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    2.8693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1525    3.2848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    4.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370    4.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572    4.0872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7633    3.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    4.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    4.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    2.8866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311    2.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600    2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    1.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    0.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448    1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    0.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  6  0  0  0
  2  1  1  0  0  0  0
  2 13  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4 11  1  1  0  0  0
  1  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8 14  1  1  0  0  0
  7  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 12  1  6  0  0  0
  8 10  1  0  0  0  0
  6 10  2  0  0  0  0
 11 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  1  0  0  0
 24 25  2  0  0  0  0
 25 30  1  0  0  0  0
 25 26  1  0  0  0  0
 30 27  1  0  0  0  0
 27 28  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005007

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

> <INCHI_KEY>
RYMZZMVNJRMUDD-HGQWONQESA-N

> <FORMULA>
C25H38O5

> <MOLECULAR_WEIGHT>
418.5662

> <EXACT_MASS>
418.271924326

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.85247192642514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.458201216333332

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914537666911102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8361812244930835

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
117.68339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
simvastatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005007
     RDKit          3D
Simvastatin
 68 70  0  0  0  0  0  0  0  0999 V2000
   -3.2088    3.0117   -1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2042    1.8740   -1.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    0.5336   -1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    0.5238   -3.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5733   -0.5145   -2.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915    0.3202   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    1.1964    0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593   -0.8098   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -1.0834    0.9735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3024   -2.2877    1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1746   -3.4947    0.7238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3664   -3.6969   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -3.6284   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0098   -2.7307    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326   -2.9325   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -2.1642   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118   -1.0627    0.4121 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3823   -1.7263    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.4800    0.3832 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6732    0.8301    1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768    2.0103    0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411    2.0935    0.4175 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5428    1.9639    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    2.2288    1.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7532    1.0464    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    2.7758    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4383    3.8281   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    4.9817   -0.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978    3.5161    0.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1139   -1.5415    0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1806    2.6991   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5302    3.8892   -2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620    3.3068   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6386    2.0207   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958    1.9564   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -0.4805   -3.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    1.1946   -3.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412    0.9166   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8772   -0.9917   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037   -1.3240   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576   -0.0707   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555   -0.3056    1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3717   -1.9702    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -2.4206    2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2117   -4.3853    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167   -3.6383    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2756   -4.7410   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2748   -3.0105   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8331   -4.4947   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2264   -3.7377   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573   -2.3271   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586   -0.4413    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870   -2.7393    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9390   -1.1318    2.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.7950    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -0.3496   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9758    0.8028    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.1398    1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625    2.9738    0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899    2.1467   -0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    1.5850   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    2.6497    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.9476    2.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2919    2.9968    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2692    1.1329    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4209    3.2603    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    1.9882   -0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -1.8335    1.8923 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 19 30  1  0
 30  9  1  0
 30 14  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  1
 10 43  1  0
 10 44  1  0
 11 45  1  1
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  6
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 23 63  1  0
 24 64  1  1
 25 65  1  0
 26 66  1  0
 26 67  1  0
 30 68  1  1
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.339   3.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.003  -1.552   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -0.020   2.483   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       4.000   1.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.659   3.834   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.698   5.356   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.018   6.132   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.006   7.654   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.682   8.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.413   7.629   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.425   6.107   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.078   8.402   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.326   8.429   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.674   5.388   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.671   3.848   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.336   3.081   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.339   3.844   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.671   3.071   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.602   1.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.004   3.076   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.400   1.588   0.000  0.00  0.00           C+0
CONECT    1   26    2    5                                                  
CONECT    2    1   13    3    4                                             
CONECT    3    2    6    7                                                  
CONECT    4    2   11    8                                                  
CONECT    5    1    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3    9                                                       
CONECT    8    4   14   10                                                  
CONECT    9    7    5   12                                                  
CONECT   10    8    6                                                       
CONECT   11    4   15                                                       
CONECT   12    9                                                            
CONECT   13    2                                                            
CONECT   14    8                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   16   20                                                       
CONECT   22   20                                                            
CONECT   23   18                                                            
CONECT   24   25                                                            
CONECT   25   24   30   26                                                  
CONECT   26    1   25                                                       
CONECT   27   30   28                                                       
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   25   27   29   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0005007
HETATM    1  C1  UNL     1      -3.209   3.012  -1.712  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.204   1.874  -1.902  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.511   0.534  -1.893  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.510   0.524  -3.026  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.573  -0.514  -2.168  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.891   0.320  -0.573  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.022   1.196   0.315  1.00  0.00           O  
HETATM    8  O2  UNL     1      -2.159  -0.810  -0.242  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.547  -1.083   0.974  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.302  -2.288   1.576  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.175  -3.495   0.724  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.366  -3.697  -0.196  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.955  -3.628  -0.046  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.010  -2.731   0.015  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.233  -2.933  -0.802  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.286  -2.164  -0.639  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.212  -1.063   0.412  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.382  -1.726   1.794  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.839  -0.480   0.383  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.673   0.830   1.005  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.377   2.010   0.468  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.841   2.093   0.418  1.00  0.00           C  
HETATM   23  C21 UNL     1       3.543   1.964   1.746  1.00  0.00           C  
HETATM   24  C22 UNL     1       5.006   2.229   1.665  1.00  0.00           C  
HETATM   25  O3  UNL     1       5.753   1.046   1.853  1.00  0.00           O  
HETATM   26  C23 UNL     1       5.427   2.776   0.312  1.00  0.00           C  
HETATM   27  C24 UNL     1       4.438   3.828  -0.037  1.00  0.00           C  
HETATM   28  O4  UNL     1       4.754   4.982  -0.419  1.00  0.00           O  
HETATM   29  O5  UNL     1       3.098   3.516   0.065  1.00  0.00           O  
HETATM   30  C25 UNL     1      -0.114  -1.542   0.884  1.00  0.00           C  
HETATM   31  H1  UNL     1      -2.181   2.699  -1.954  1.00  0.00           H  
HETATM   32  H2  UNL     1      -3.530   3.889  -2.309  1.00  0.00           H  
HETATM   33  H3  UNL     1      -3.262   3.307  -0.649  1.00  0.00           H  
HETATM   34  H4  UNL     1      -4.639   2.021  -2.925  1.00  0.00           H  
HETATM   35  H5  UNL     1      -4.996   1.956  -1.151  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.439  -0.480  -3.505  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.910   1.195  -3.813  1.00  0.00           H  
HETATM   38  H8  UNL     1      -1.541   0.917  -2.710  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.877  -0.992  -1.202  1.00  0.00           H  
HETATM   40  H10 UNL     1      -4.104  -1.324  -2.776  1.00  0.00           H  
HETATM   41  H11 UNL     1      -5.458  -0.071  -2.627  1.00  0.00           H  
HETATM   42  H12 UNL     1      -1.656  -0.306   1.733  1.00  0.00           H  
HETATM   43  H13 UNL     1      -3.372  -1.970   1.579  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.982  -2.421   2.612  1.00  0.00           H  
HETATM   45  H15 UNL     1      -2.212  -4.385   1.427  1.00  0.00           H  
HETATM   46  H16 UNL     1      -4.317  -3.638   0.330  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.276  -4.741  -0.601  1.00  0.00           H  
HETATM   48  H18 UNL     1      -3.275  -3.011  -1.054  1.00  0.00           H  
HETATM   49  H19 UNL     1      -0.833  -4.495  -0.694  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.226  -3.738  -1.540  1.00  0.00           H  
HETATM   51  H21 UNL     1       3.157  -2.327  -1.237  1.00  0.00           H  
HETATM   52  H22 UNL     1       3.059  -0.441   0.243  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.987  -2.739   1.824  1.00  0.00           H  
HETATM   54  H24 UNL     1       1.939  -1.132   2.600  1.00  0.00           H  
HETATM   55  H25 UNL     1       3.478  -1.795   2.032  1.00  0.00           H  
HETATM   56  H26 UNL     1       0.614  -0.350  -0.738  1.00  0.00           H  
HETATM   57  H27 UNL     1       0.976   0.803   2.124  1.00  0.00           H  
HETATM   58  H28 UNL     1      -0.411   1.140   1.107  1.00  0.00           H  
HETATM   59  H29 UNL     1       0.963   2.974   0.932  1.00  0.00           H  
HETATM   60  H30 UNL     1       0.990   2.147  -0.614  1.00  0.00           H  
HETATM   61  H31 UNL     1       3.395   1.585  -0.355  1.00  0.00           H  
HETATM   62  H32 UNL     1       3.099   2.650   2.513  1.00  0.00           H  
HETATM   63  H33 UNL     1       3.392   0.948   2.159  1.00  0.00           H  
HETATM   64  H34 UNL     1       5.292   2.997   2.409  1.00  0.00           H  
HETATM   65  H35 UNL     1       6.269   1.133   2.693  1.00  0.00           H  
HETATM   66  H36 UNL     1       6.421   3.260   0.470  1.00  0.00           H  
HETATM   67  H37 UNL     1       5.493   1.988  -0.451  1.00  0.00           H  
HETATM   68  H38 UNL     1       0.186  -1.833   1.892  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4    5    6
CONECT    4   36   37   38
CONECT    5   39   40   41
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   30   42
CONECT   10   11   43   44
CONECT   11   12   13   45
CONECT   12   46   47   48
CONECT   13   14   14   49
CONECT   14   15   30
CONECT   15   16   16   50
CONECT   16   17   51
CONECT   17   18   19   52
CONECT   18   53   54   55
CONECT   19   20   30   56
CONECT   20   21   57   58
CONECT   21   22   59   60
CONECT   22   23   29   61
CONECT   23   24   62   63
CONECT   24   25   26   64
CONECT   25   65
CONECT   26   27   66   67
CONECT   27   28   28   29
CONECT   30   68
END

HMDB0005007
     RDKit          3D
Simvastatin
 68 70  0  0  0  0  0  0  0  0999 V2000
   -3.2088    3.0117   -1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2042    1.8740   -1.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    0.5336   -1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    0.5238   -3.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5733   -0.5145   -2.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915    0.3202   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    1.1964    0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593   -0.8098   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -1.0834    0.9735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3024   -2.2877    1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1746   -3.4947    0.7238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3664   -3.6969   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -3.6284   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0098   -2.7307    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326   -2.9325   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -2.1642   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118   -1.0627    0.4121 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3823   -1.7263    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.4800    0.3832 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6732    0.8301    1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768    2.0103    0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411    2.0935    0.4175 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5428    1.9639    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    2.2288    1.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7532    1.0464    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    2.7758    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4383    3.8281   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    4.9817   -0.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978    3.5161    0.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1139   -1.5415    0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1806    2.6991   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5302    3.8892   -2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620    3.3068   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6386    2.0207   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958    1.9564   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -0.4805   -3.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    1.1946   -3.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412    0.9166   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8772   -0.9917   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037   -1.3240   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4576   -0.0707   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555   -0.3056    1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3717   -1.9702    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -2.4206    2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2117   -4.3853    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167   -3.6383    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2756   -4.7410   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2748   -3.0105   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8331   -4.4947   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2264   -3.7377   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573   -2.3271   -1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586   -0.4413    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870   -2.7393    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9390   -1.1318    2.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.7950    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -0.3496   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9758    0.8028    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.1398    1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625    2.9738    0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899    2.1467   -0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    1.5850   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    2.6497    2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.9476    2.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2919    2.9968    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2692    1.1329    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4209    3.2603    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    1.9882   -0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -1.8335    1.8923 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 19 30  1  0
 30  9  1  0
 30 14  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  9 42  1  1
 10 43  1  0
 10 44  1  0
 11 45  1  1
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  6
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  6
 23 62  1  0
 23 63  1  0
 24 64  1  1
 25 65  1  0
 26 66  1  0
 26 67  1  0
 30 68  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2-Dimethylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8ar)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one	ChEBI
MK-733	ChEBI
Simvastatina	ChEBI
Simvastatine	ChEBI
Simvastatinum	ChEBI
Zocor	ChEBI
2,2-Dimethylbutyrate, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8ar)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one	Generator
(+)-Simvastatin	HMDB
Cholestat	HMDB
Denan	HMDB
Eucor	HMDB
Kolestevan	HMDB
Lipex	HMDB
Lipinorm	HMDB
Liponorm	HMDB
Lipovas	HMDB
Lodales	HMDB
Modutrol	HMDB
Nor-vastina	HMDB
Pepstatin	HMDB
Rechol	HMDB
Simcor	HMDB
Simovil	HMDB
Simvastatin lactone	HMDB
Simvotin	HMDB
Sinvacor	HMDB
Sinvascor	HMDB
Sivastin	HMDB
Statin	HMDB
Synvinolin	HMDB
Valemia	HMDB
Velostatin	HMDB
Zocord	HMDB

Chemical Formula

C₂₅H₃₈O₅

Average Molecular Weight

418.5662

Monoisotopic Molecular Weight

418.271924326

IUPAC Name

(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

Traditional Name

simvastatin

CAS Registry Number

79902-63-9

SMILES

[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC

InChI Identifier

InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1

InChI Key

RYMZZMVNJRMUDD-HGQWONQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

statin (semi-synthetic) (CHEBI:9150 )
fatty acid ester (CHEBI:9150 )
delta-lactone (CHEBI:9150 )
carbobicyclic compound (CHEBI:9150 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14691614)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0005007)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0005007)
Membrane (HMDB: HMDB0005007)

Tissue substructure

Muscle (HMDB: HMDB0005007)

Source

Exogenous

Exogenous (HMDB: HMDB0005007)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Simvastatin Action Pathway (PathBank: SMP0000082)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	135 - 138 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.012 g/L	Not Available
LogP	4.68	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	4.51	ALOGPS
logP	4.46	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.68 m³·mol⁻¹	ChemAxon
Polarizability	47.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	202.851	31661259
DarkChem	[M-H]-	199.444	31661259
DeepCCS	[M-2H]-	244.362	30932474
DeepCCS	[M+Na]+	219.035	30932474
AllCCS	[M+H]+	205.4	32859911
AllCCS	[M+H-H2O]+	203.1	32859911
AllCCS	[M+NH4]+	207.5	32859911
AllCCS	[M+Na]+	208.1	32859911
AllCCS	[M-H]-	205.6	32859911
AllCCS	[M+Na-2H]-	207.1	32859911
AllCCS	[M+HCOO]-	208.9	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. Predicted by Afia on May 17, 2022.	8.27 minutes	32390414
Predicted by Siyang on May 30, 2022	21.6027 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3574.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	530.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	250.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	212.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	976.5 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	959.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1759.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	690.6 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	1910.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	587.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	529.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	224.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	453.3 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Simvastatin	[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC	3779.9	Standard polar	33892256
Simvastatin	[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC	2909.0	Standard non polar	33892256
Simvastatin	[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC	3142.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Simvastatin,1TMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O[Si](C)(C)C)CC(=O)O3)[C@H]21	2994.3	Semi standard non polar	33892256
Simvastatin,1TBDMS,isomer #1	CCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)O3)[C@H]21	3225.0	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Simvastatin Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.044 +/- 0.011 uM	Adult (>18 years old)	Both	Normal	14691614	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00641

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023580

KNApSAcK ID

Not Available

Chemspider ID

49179

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Simvastatin

METLIN ID

2443

PubChem Compound

54454

PDB ID

Not Available

ChEBI ID

9150

Food Biomarker Ontology

Not Available

VMH ID

SMV

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Willard, Alvin K.; Smith, Robert L.; Hoffman, William F. 6(R)-[2-(8-acyloxy-2-methyl-6-methyl (or hydrogen)-polyhydro-1-naphthyl)ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones, the hydroxy acid forms of these pyranones, salts and esters thereof, and a pharmaceutical antihypercholesterolemic composition containing them. Eur. Pat. Appl. (1981), 54 pp. CODEN: EPXXDW EP 33538 19810812 CAN 95:219968 AN 1981:619968

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mahboobi SK, Shohat EZ, Jellinek SP, Rose M: Systemic infections can decrease the threshold of statin-induced muscle injury. South Med J. 2006 Apr;99(4):403-4. [PubMed:16634254 ]
Antons KA, Williams CD, Baker SK, Phillips PS: Clinical perspectives of statin-induced rhabdomyolysis. Am J Med. 2006 May;119(5):400-9. [PubMed:16651050 ]
Tsivgoulis G, Spengos K, Karandreas N, Panas M, Kladi A, Manta P: Presymptomatic neuromuscular disorders disclosed following statin treatment. Arch Intern Med. 2006 Jul 24;166(14):1519-24. [PubMed:16864763 ]
Finsterer J, Zuntner G: Rhabdomyolysis from Simvastatin triggered by infection and muscle exertion. South Med J. 2005 Aug;98(8):827-9. [PubMed:16144183 ]
Soininen K, Niemi M, Kilkki E, Strandberg T, Kivisto KT: Muscle symptoms associated with statins: a series of twenty patients. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):51-4. [PubMed:16433891 ]
Davidson MH, Maccubbin D, Stepanavage M, Strony J, Musliner T: Striated muscle safety of ezetimibe/simvastatin (Vytorin). Am J Cardiol. 2006 Jan 15;97(2):223-8. Epub 2005 Nov 21. [PubMed:16442367 ]
Hellinger FJ, Encinosa WE: Inappropriate drug combinations among privately insured patients with HIV disease. Med Care. 2005 Sep;43(9 Suppl):III53-62. [PubMed:16116309 ]
Wolozin B, Wang SW, Li NC, Lee A, Lee TA, Kazis LE: Simvastatin is associated with a reduced incidence of dementia and Parkinson's disease. BMC Med. 2007 Jul 19;5:20. [PubMed:17640385 ]

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-hydroxy-3-methylglutaryl-coenzyme A reductase

General function:: Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:: Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:: HMGCR
Uniprot ID:: P04035
Molecular weight:: 97475.155

Enzyme Details

2. 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

Enzyme Details

3. Activin receptor type-1

General function:: Involved in receptor signaling protein serine/threonine kinase activity
Specific function:: On ligand binding, forms a receptor complex consisting of two type II and two type I transmembrane serine/threonine kinases. Type II receptors phosphorylate and activate type I receptors which autophosphorylate, then bind and activate SMAD transcriptional regulators. Receptor for activin. May be involved for left-right pattern formation during embryogenesis
Gene Name:: ACVR1
Uniprot ID:: Q04771
Molecular weight:: 57152.4

Enzyme Details

4. Mitogen-activated protein kinase 3

General function:: Involved in MAP kinase activity
Specific function:: Involved in both the initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors such as ELK-1. Phosphorylates EIF4EBP1; required for initiation of translation. Phosphorylates microtubule-associated protein 2 (MAP2). Phosphorylates SPZ1. Phosphorylates heat shock factor protein 4 (HSF4)
Gene Name:: MAPK3
Uniprot ID:: P27361
Molecular weight:: 43135.2

Enzyme Details

5. Cytochrome P450 2C8

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

Enzyme Details

6. Ras-related C3 botulinum toxin substrate 1

General function:: Involved in GTP binding
Specific function:: Isoform B has an accelerated GEF-independent GDP/GTP exchange and an impaired GTP hydrolysis, which is restored partially by GTPase-activating proteins. It is able to bind to the GTPase-binding domain of PAK but not full-length PAK in a GTP- dependent manner, suggesting that the insertion does not completely abolish effector interaction
Gene Name:: RAC1
Uniprot ID:: P63000
Molecular weight:: 21449.9

Enzyme Details

7. Plasminogen activator inhibitor 1

General function:: Involved in serine-type endopeptidase inhibitor activity
Specific function:: This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, and protein C. Its rapid interaction with TPA may function as a major control point in the regulation of fibrinolysis
Gene Name:: SERPINE1
Uniprot ID:: P05121
Molecular weight:: 45059.7

Enzyme Details

8. C-C motif chemokine 2

General function:: Involved in chemokine activity
Specific function:: Chemotactic factor that attracts monocytes and basophils but not neutrophils or eosinophils. Augments monocyte anti-tumor activity. Has been implicated in the pathogenesis of diseases characterized by monocytic infiltrates, like psoriasis, rheumatoid arthritis or atherosclerosis. May be involved in the recruitment of monocytes into the arterial wall during the disease process of atherosclerosis
Gene Name:: CCL2
Uniprot ID:: P13500
Molecular weight:: 11024.9

Enzyme Details

9. Transforming protein RhoA

General function:: Involved in GTP binding
Specific function:: Regulates a signal transduction pathway linking plasma membrane receptors to the assembly of focal adhesions and actin stress fibers. Serves as a target for the yopT cysteine peptidase from Yersinia pestis, vector of the plague, and Yersinia pseudotuberculosis, which causes gastrointestinal disorders. May be an activator of PLCE1. Activated by ARHGEF2, which promotes the exchange of GDP for GTP
Gene Name:: RHOA
Uniprot ID:: P61586
Molecular weight:: 21767.9

Enzyme Details

10. Tumor necrosis factor

General function:: Involved in tumor necrosis factor receptor binding
Specific function:: Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:: TNF
Uniprot ID:: P01375
Molecular weight:: 25644.1

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Showing metabocard for Simvastatin (HMDB0005007)

MOL for HMDB0005007 (Simvastatin)

3D MOL for HMDB0005007 (Simvastatin)

3D SDF for HMDB0005007 (Simvastatin)

3D-SDF for HMDB0005007 (Simvastatin)

PDB for HMDB0005007 (Simvastatin)

3D PDB for HMDB0005007 (Simvastatin)

SMILES for HMDB0005007 (Simvastatin)

INCHI for HMDB0005007 (Simvastatin)

Structure for HMDB0005007 (Simvastatin)

3D Structure for HMDB0005007 (Simvastatin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes