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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:13 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002835

Secondary Accession Numbers

HMDB02835

Metabolite Identification

Common Name

Danazol

Description

Danazol is a synthetic steroid with anti-oestrogenic and anti progestogenic activity, and weak androgenic properties. Danazol suppresses oestrogen and progesterone receptors in the endometrium, leading to endometrial atrophy (thinning of the lining of the uterus) and reduced menstrual loss and to amenorrhoea in some women. Danazol significantly lowers the duration of menses when compared with NSAIDs and a progesterone releasing IUD; however, caused more adverse events than NSAIDs and progestogens. The use of Danazol may be limited by its side effect profile, its acceptability to women and the need for continuing treatment. Because danazol is structurally related to the anabolic steroid stanozolol, its use should be questioned. Derivatization methods and GC/MS data are used to implement danazol detection in routine screening and confirmation procedures in doping analysis. Danazol main metabolite ethisterone is excreted relatively fast in urine. (PMID: 17636649 , 1640693 , 16288903 ).

Structure

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

1406
  Mrv1652305271900082D          

 28 32  0  0  1  0            999 V2000
    6.9568   -1.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0778    1.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5935    1.1328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4022    0.3306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4086   -0.4993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6772    0.7344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9872    0.3361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2973    0.7344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6899   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1958   -0.7462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9745   -0.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855    0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6772    1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6751   -0.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973    1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4148   -1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    0.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973   -0.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8448   -1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0778    0.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4938   -1.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4623    0.9651    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2267    1.0574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4329    0.0216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 26  1  1  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  6  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 27  1  6  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 28  1  1  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  6  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 20  1  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 15 17  1  0  0  0  0
 15 21  2  0  0  0  0
 18 22  1  0  0  0  0
 20 25  3  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END

HMDB0002835
     RDKit          3D
Danazol
 52 56  0  0  0  0  0  0  0  0999 V2000
    4.1427   -2.1208    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447   -0.9744   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779    0.4208   -0.3974 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4446    0.8290   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421    1.2952    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891    1.2629    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245    0.2272    0.8000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2315    0.3566    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2252    2.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -0.4198    2.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -0.5290    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482   -1.2555    1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -1.4027   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -2.0877   -0.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7882   -1.9109   -1.6427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974   -1.1155   -2.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9410   -0.7749   -1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401    0.0676   -1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    0.1798   -0.1313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9578    1.6708    0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4994   -0.2892   -0.2419 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0971   -0.1458   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5857   -0.4268   -1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    0.5639   -0.6248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8610    1.9554   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2988   -3.1339    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.2172   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094    0.8516    1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677    2.3113    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    2.2485    1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6172    1.0318    2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -0.7731    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    1.4648    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.3544    3.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -1.2368    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -1.2784    2.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.4731    2.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -1.7839    1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8500   -0.7633   -3.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -0.1970   -2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    1.1060   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    2.2716   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916    2.0457    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054    1.7965    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238   -1.3991   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1510    0.8283   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244   -0.9572   -2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248   -0.4280   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -1.4414   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    2.6316   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    2.4601   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661    1.9159   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  3  1  0
 24  7  1  0
 21  8  1  0
 19 11  1  0
 17 13  2  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  1
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
M  END

1406
  Mrv1652305271900082D          

 28 32  0  0  1  0            999 V2000
    6.9568   -1.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0778    1.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5935    1.1328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4022    0.3306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4086   -0.4993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6772    0.7344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9872    0.3361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2973    0.7344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6899   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1958   -0.7462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9745   -0.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855    0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6772    1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6751   -0.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973    1.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4148   -1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    0.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973   -0.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8448   -1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0778    0.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4938   -1.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4623    0.9651    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2267    1.0574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4329    0.0216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 26  1  1  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  6  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 27  1  6  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 28  1  1  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  6  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 20  1  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 15 17  1  0  0  0  0
 15 21  2  0  0  0  0
 18 22  1  0  0  0  0
 20 25  3  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002835

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1

> <INCHI_KEY>
POZRVZJJTULAOH-LHZXLZLDSA-N

> <FORMULA>
C22H27NO2

> <MOLECULAR_WEIGHT>
337.4553

> <EXACT_MASS>
337.204179113

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.43900475915706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.462082191666666

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.59493194220648

> <JCHEM_PKA_STRONGEST_BASIC>
0.24625761539361124

> <JCHEM_POLAR_SURFACE_AREA>
46.260000000000005

> <JCHEM_REFRACTIVITY>
98.5352

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002835
     RDKit          3D
Danazol
 52 56  0  0  0  0  0  0  0  0999 V2000
    4.1427   -2.1208    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447   -0.9744   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779    0.4208   -0.3974 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4446    0.8290   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421    1.2952    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891    1.2629    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245    0.2272    0.8000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2315    0.3566    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2252    2.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -0.4198    2.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -0.5290    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482   -1.2555    1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -1.4027   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -2.0877   -0.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7882   -1.9109   -1.6427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974   -1.1155   -2.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9410   -0.7749   -1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401    0.0676   -1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    0.1798   -0.1313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9578    1.6708    0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4994   -0.2892   -0.2419 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0971   -0.1458   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5857   -0.4268   -1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    0.5639   -0.6248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8610    1.9554   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2988   -3.1339    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.2172   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094    0.8516    1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677    2.3113    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    2.2485    1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6172    1.0318    2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -0.7731    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    1.4648    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.3544    3.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -1.2368    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -1.2784    2.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.4731    2.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -1.7839    1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8500   -0.7633   -3.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -0.1970   -2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    1.1060   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    2.2716   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916    2.0457    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054    1.7965    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238   -1.3991   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1510    0.8283   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244   -0.9572   -2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248   -0.4280   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -1.4414   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    2.6316   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    2.4601   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661    1.9159   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  3  1  0
 24  7  1  0
 21  8  1  0
 19 11  1  0
 17 13  2  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  1
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1406                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      12.986  -2.812   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.879   3.361   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       2.975   2.115   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      11.951   0.617   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.963  -0.932   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.597   1.371   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.309   0.627   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.022   1.371   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.621  -1.707   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.432  -1.393   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.286  -0.922   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.413   1.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.597   2.858   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.327  -0.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.022   2.858   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.974  -2.419   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.309   3.602   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.692   0.576   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.022  -0.116   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.644  -2.255   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.692   3.653   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.344   1.340   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.344   2.889   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.879   0.868   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.855  -3.118   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      12.063   1.802   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      11.623   1.974   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.275   0.040   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2    3   23                                                       
CONECT    3    2   24                                                       
CONECT    4    5    6   12   26                                             
CONECT    5    4    9   10   16                                             
CONECT    6    4    7   13   27                                             
CONECT    7    6    8   11   28                                             
CONECT    8    7   15   18   19                                             
CONECT    9    5   11                                                       
CONECT   10    1    5   14   20                                             
CONECT   11    7    9                                                       
CONECT   12    4   14                                                       
CONECT   13    6   17                                                       
CONECT   14   10   12                                                       
CONECT   15    8   17   21                                                  
CONECT   16    5                                                            
CONECT   17   13   15                                                       
CONECT   18    8   22                                                       
CONECT   19    8                                                            
CONECT   20   10   25                                                       
CONECT   21   15   23                                                       
CONECT   22   18   23   24                                                  
CONECT   23    2   21   22                                                  
CONECT   24    3   22                                                       
CONECT   25   20                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0002835
HETATM    1  C1  UNL     1       4.143  -2.121   0.324  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.945  -0.974  -0.000  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.678   0.421  -0.397  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.445   0.829  -1.455  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.842   1.295   0.834  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.489   1.263   1.554  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.724   0.227   0.800  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.232   0.357   0.890  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.242  -0.225   2.183  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.705  -0.420   2.326  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.462  -0.529   1.061  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.548  -1.256   1.051  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.339  -1.403  -0.163  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.469  -2.088  -0.404  1.00  0.00           O  
HETATM   15  N1  UNL     1      -5.788  -1.911  -1.643  1.00  0.00           N  
HETATM   16  C13 UNL     1      -4.897  -1.116  -2.257  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.941  -0.775  -1.296  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.740   0.068  -1.363  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.948   0.180  -0.131  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.958   1.671   0.278  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.499  -0.289  -0.242  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.097  -0.146  -1.589  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.586  -0.427  -1.521  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.192   0.564  -0.625  1.00  0.00           C  
HETATM   25  C22 UNL     1       1.861   1.955  -1.037  1.00  0.00           C  
HETATM   26  H1  UNL     1       4.299  -3.134   0.611  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.238   0.217  -1.528  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.609   0.852   1.526  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.168   2.311   0.605  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.021   2.249   1.375  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.617   1.032   2.629  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.102  -0.773   1.042  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.035   1.465   0.969  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.118   0.354   3.072  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.247  -1.237   2.301  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.963  -1.278   2.989  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.125   0.473   2.876  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.910  -1.784   1.953  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.850  -0.763  -3.269  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.118  -0.197  -2.262  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.153   1.106  -1.620  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.277   2.272  -0.330  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.992   2.046   0.000  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.905   1.796   1.361  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.524  -1.399  -0.003  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.151   0.828  -2.016  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.324  -0.957  -2.233  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.025  -0.428  -2.558  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.687  -1.441  -1.071  1.00  0.00           H  
HETATM   50  H25 UNL     1       2.756   2.632  -1.038  1.00  0.00           H  
HETATM   51  H26 UNL     1       1.108   2.460  -0.436  1.00  0.00           H  
HETATM   52  H27 UNL     1       1.566   1.916  -2.126  1.00  0.00           H  
CONECT    1    2    2    2   26
CONECT    2    3
CONECT    3    4    5   24
CONECT    4   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   24   32
CONECT    8    9   21   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   12   19
CONECT   12   13   38
CONECT   13   14   17   17
CONECT   14   15
CONECT   15   16   16
CONECT   16   17   39
CONECT   17   18
CONECT   18   19   40   41
CONECT   19   20   21
CONECT   20   42   43   44
CONECT   21   22   45
CONECT   22   23   46   47
CONECT   23   24   48   49
CONECT   24   25
CONECT   25   50   51   52
END

HMDB0002835
     RDKit          3D
Danazol
 52 56  0  0  0  0  0  0  0  0999 V2000
    4.1427   -2.1208    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9447   -0.9744   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779    0.4208   -0.3974 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4446    0.8290   -1.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421    1.2952    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891    1.2629    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245    0.2272    0.8000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2315    0.3566    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2252    2.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -0.4198    2.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -0.5290    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482   -1.2555    1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -1.4027   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -2.0877   -0.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7882   -1.9109   -1.6427 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974   -1.1155   -2.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9410   -0.7749   -1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401    0.0676   -1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481    0.1798   -0.1313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9578    1.6708    0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4994   -0.2892   -0.2419 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0971   -0.1458   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5857   -0.4268   -1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    0.5639   -0.6248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8610    1.9554   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2988   -3.1339    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.2172   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094    0.8516    1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677    2.3113    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    2.2485    1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6172    1.0318    2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016   -0.7731    1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0352    1.4648    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    0.3544    3.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -1.2368    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -1.2784    2.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.4731    2.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -1.7839    1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8500   -0.7633   -3.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182   -0.1970   -2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    1.1060   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    2.2716   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916    2.0457    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054    1.7965    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238   -1.3991   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1510    0.8283   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244   -0.9572   -2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248   -0.4280   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -1.4414   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    2.6316   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    2.4601   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661    1.9159   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  3  1  0
 24  7  1  0
 21  8  1  0
 19 11  1  0
 17 13  2  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  1
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cyclomen	ChEBI
Danazolum	ChEBI
Danocrine	ChEBI
(17a)-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol	HMDB
1-Ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-cyclopenta[7,8]phenanthro[3,2-D]isoxazol-1-ol	HMDB
17 alpha-Pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol	HMDB
17a-Pregna-2,4-dien-20-yne-[2,3-D]isoxazole-17b-ol	HMDB
17a-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol	HMDB
1H-Cyclopenta[7,8]phenanthro[3,2-D]isoxazole- pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol deriv.	HMDB
Bonzol	HMDB
Chronogyn	HMDB
Danol	HMDB
Danovaol	HMDB
Danzol	HMDB
Ladogal	HMDB
Winobanin	HMDB
Alphapharm brand OF danazol	HMDB
Kendrick brand OF danazol	HMDB
Sanofi brand OF danazol	HMDB
Danatrol	HMDB
Danazant	HMDB
Danazol-ratiopharm	HMDB
Danoval	HMDB
Ratiopharm brand OF danazol	HMDB
Antigen brand OF danazol	HMDB
Azol	HMDB
Norciden	HMDB
Panacrine	HMDB
Sanofi synthelabo brand OF danazol	HMDB
Sanofi winthrop brand OF danazol	HMDB
Danazol ratiopharm	HMDB

Chemical Formula

C₂₂H₂₇NO₂

Average Molecular Weight

337.4553

Monoisotopic Molecular Weight

337.204179113

IUPAC Name

(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol

Traditional Name

(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol

CAS Registry Number

17230-88-5

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3

InChI Identifier

InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1

InChI Key

POZRVZJJTULAOH-LHZXLZLDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Ynone
Heteroaromatic compound
Azole
Cyclic alcohol
Tertiary alcohol
Isoxazole
Acetylide
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4315 )
17beta-hydroxy steroid (CHEBI:4315 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002835)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0002835)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002835)

Source

Exogenous

Exogenous (HMDB: HMDB0002835)

Food

Food (HMDB: HMDB0002835)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002835)

Molecular messenger

Signaling molecule (HMDB: HMDB0002835)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002835)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002835)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	225.6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	4.081	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.46	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.59	ChemAxon
pKa (Strongest Basic)	0.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	98.54 m³·mol⁻¹	ChemAxon
Polarizability	38.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.086	31661259
DarkChem	[M-H]-	174.92	31661259
DeepCCS	[M-2H]-	210.138	30932474
DeepCCS	[M+Na]+	184.261	30932474
AllCCS	[M+H]+	185.1	32859911
AllCCS	[M+H-H2O]+	182.2	32859911
AllCCS	[M+NH4]+	187.8	32859911
AllCCS	[M+Na]+	188.6	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	191.7	32859911
AllCCS	[M+HCOO]-	191.8	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.	7.81 minutes	32390414
Predicted by Siyang on May 30, 2022	19.0476 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2590.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	556.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	242.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	844.4 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	995.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1571.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	493.2 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	1667.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	581.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	488.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	428.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	702.7 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Danazol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3	4044.9	Standard polar	33892256
Danazol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3	2871.3	Standard non polar	33892256
Danazol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3	2971.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Danazol,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC5=C(C=NO5)C[C@]4(C)[C@H]3CC[C@@]21C	3060.0	Semi standard non polar	33892256
Danazol,1TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC5=C(C=NO5)C[C@]4(C)[C@H]3CC[C@@]21C	3326.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Danazol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0669000000-7afc135d5b1e92134191	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Danazol GC-MS (1 TMS) - 70eV, Positive	splash10-000x-2479000000-d5f94bb7e7215a30f820	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Danazol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0009000000-9e745b8feecd354f6618	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-01b9-6902000000-854476472755ef5419e5	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9100000000-0d62c0c1b53c1cea5a25	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol , positive-QTOF	splash10-000i-0329000000-56adc37fd83dfa3c686f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol , positive-QTOF	splash10-05ia-3931000000-1490f6c4984a84016076	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 90V, Positive-QTOF	splash10-002f-6900000000-529d2d24864b26fdd611	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 90V, Positive-QTOF	splash10-002f-6900000000-01f21f6ea357e6649d15	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 30V, Positive-QTOF	splash10-000i-1309000000-271d4ce8113e1bf16016	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 45V, Positive-QTOF	splash10-00dj-2910000000-3af637f5ddbf8cfd6b84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 45V, Positive-QTOF	splash10-00dj-2920000000-ba6bb4b948be2171d864	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 60V, Positive-QTOF	splash10-05tg-3900000000-29df3c1f08b04956955d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 15V, Positive-QTOF	splash10-000i-0009000000-5fc69729a45a40e94073	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 75V, Positive-QTOF	splash10-002f-4900000000-7ba349192301fd4e5013	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Danazol 60V, Positive-QTOF	splash10-05tg-3900000000-a692616aee182eeb1270	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 10V, Positive-QTOF	splash10-000i-0119000000-d7acb78e38c02e285d4f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 20V, Positive-QTOF	splash10-01wr-0289000000-2db311b410937e72f25a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 40V, Positive-QTOF	splash10-000j-3690000000-5eb98df42b0016f9967a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 10V, Negative-QTOF	splash10-000i-0009000000-d1a89ea3e6c72ff1ab88	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 20V, Negative-QTOF	splash10-000i-0009000000-71fbd4000b06296a8386	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 40V, Negative-QTOF	splash10-00e9-2089000000-24b6d7f3ec074a6c2b59	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 10V, Positive-QTOF	splash10-000i-0019000000-2626c30d979a970252f0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 20V, Positive-QTOF	splash10-007y-0982000000-4cf29ec44560862d68c7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 40V, Positive-QTOF	splash10-1001-1890000000-24565065bfdf6e8edf39	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 10V, Negative-QTOF	splash10-000i-0009000000-8413c28ca2b1374741c7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Danazol 20V, Negative-QTOF	splash10-000i-0009000000-3424fea43411af836104	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01406

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023073

KNApSAcK ID

Not Available

Chemspider ID

26436

KEGG Compound ID

C06938

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Danazol

METLIN ID

Not Available

PubChem Compound

28417

PDB ID

Not Available

ChEBI ID

4315

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Raczkowska, Sabina; Lypacewicz, Maria K.; Chojecka-Koryn, Ewa; Jaworska, Romana; Wasiak, Teresa; Mozolowski, Felicjan; Wajcht, Jozef. Method of obtaining highly pure danazol. Pol. (1991), 3 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Beaumont H, Augood C, Duckitt K, Lethaby A: Danazol for heavy menstrual bleeding. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD001017. [PubMed:17636649 ]
de Oca Porto RM, Fernandez AR, Brito DM, Vidal TC, Diaz AL: Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 2;830(1):178-83. Epub 2005 Nov 8. [PubMed:16288903 ]
de Boer D, de Jong EG, Maes RA: The detection of danazol and its significance in doping analysis. J Anal Toxicol. 1992 Jan-Feb;16(1):14-8. [PubMed:1640693 ]

Enzymes

Enzyme Details

1. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

Enzyme Details

2. Sex hormone-binding globulin

General function:: Involved in androgen binding
Specific function:: Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration
Gene Name:: SHBG
Uniprot ID:: P04278
Molecular weight:: 43778.8

Enzyme Details

3. 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

4. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

Enzyme Details

5. Gonadotropin-releasing hormone receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle- stimulating hormone (FSH). This receptor mediates its action by association with G-proteins that activate a phosphatidylinositol- calcium second messenger system. Isoform 2 may act as an inhibitor of GnRH-R signaling
Gene Name:: GNRHR
Uniprot ID:: P30968
Molecular weight:: 37730.4

Enzyme Details

6. Putative gonadotropin-releasing hormone II receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for gonadotropin releasing hormone II (GnRH II). This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system (Potential)
Gene Name:: GNRHR2
Uniprot ID:: Q96P88
Molecular weight:: 19031.1

Enzyme Details

7. N-acetylated-alpha-linked acidic dipeptidase-like protein

General function:: Involved in peptidase activity
Specific function:: NAALADase-like activity unknown. Has no NAAG hydrolyzing activity. Exhibits a dipeptidyl-peptidase IV type activity. In vitro, cleaves Gly-Pro-AMC
Gene Name:: NAALADL1
Uniprot ID:: Q9UQQ1
Molecular weight:: 80566.9

Showing metabocard for Danazol (HMDB0002835)

MOL for HMDB0002835 (Danazol)

3D MOL for HMDB0002835 (Danazol)

3D SDF for HMDB0002835 (Danazol)

3D-SDF for HMDB0002835 (Danazol)

PDB for HMDB0002835 (Danazol)

3D PDB for HMDB0002835 (Danazol)

SMILES for HMDB0002835 (Danazol)

INCHI for HMDB0002835 (Danazol)

Structure for HMDB0002835 (Danazol)

3D Structure for HMDB0002835 (Danazol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes