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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000554

Secondary Accession Numbers

HMDB00554

Metabolite Identification

Common Name

Dihydroandrosterone

Description

Dihydroandrosterone is a major metabolite of testosterone. Dihydroandrosterone is the main steroid produced by the immature ovary; at puberty the synthesis of steroids shifts toward 4-ene-3-oxo steroids. testosterone 5a-reduced metabolites, including dihydrotestosterone are produced in the anterior pituitary and the central nervous system. Anabolic androgen steroid (AAS) are one of primary performance-enhancing substances abused by athletes. To defeat doping controls, athletes changed to take endogenous androgens from the application of synthetic AAS. testosterone was one candidate of endogenous androgens abused in sports. testosterone and its relevant steroids in urine is detected and monitored with GC/MS. The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. (PMID: 17112575 , 6243214 , 491593 , 491592 ).

Structure

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

5a-Androstane-3a,17b-diol.mol
  Mrv1652305271900092D          

 25 28  0  0  0  0            999 V2000
   -2.0637   -1.1385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0637   -0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.1385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0797   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    1.1789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.9240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.5115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
  1 20  1  6  0  0  0
 12 21  1  1  0  0  0
  5 22  1  6  0  0  0
 17 23  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  6  0  0  0
M  END

HMDB0000554
     RDKit          3D
Dihydroandrosterone
 53 56  0  0  0  0  0  0  0  0999 V2000
    2.9360   -0.4092   -1.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -0.3349   -0.2686 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1180   -1.5478    0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995   -1.6573   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.4452    0.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5585    0.7625   -0.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2552    2.0103   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    1.7851   -0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    0.6915   -0.2246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6856    0.5159   -0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.4977    0.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5302    0.1100    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485   -1.0018    1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173   -1.5157    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373   -0.5990   -0.2168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6379   -1.3215   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    0.8665    0.1416 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7461    1.9957   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412    1.5558    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    0.0511    0.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1105   -0.6079   -0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5994   -1.3806   -2.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.4223   -2.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -0.3386   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983   -1.5601    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -2.4423   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2571   -2.6003    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733   -1.6522   -1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -0.2974    1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575    0.5367   -1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2674    2.8391   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    2.2384    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    2.6691   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.4007   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    1.0479    0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156    0.2598   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1942    1.5208   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7905   -1.3500   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5674    1.0712    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028   -1.8685    1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201   -0.2517    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -1.6126    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -2.5516    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832   -0.7621   -2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294   -1.5310   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825   -2.3283   -1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.8287    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    2.9611    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280    2.2086   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551    2.0134    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229    1.8692   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0570   -0.2283    1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598   -1.5380   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  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  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  1
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  1
 21 53  1  0
M  END

5a-Androstane-3a,17b-diol.mol
  Mrv1652305271900092D          

 25 28  0  0  0  0            999 V2000
   -2.0637   -1.1385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0637   -0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    0.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.1385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0797   -1.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    1.1789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.9240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6348    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.5115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.7260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
  1 20  1  6  0  0  0
 12 21  1  1  0  0  0
  5 22  1  6  0  0  0
 17 23  1  6  0  0  0
  8 24  1  1  0  0  0
  9 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000554

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
CBMYJHIOYJEBSB-KHOSGYARSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.4562

> <EXACT_MASS>
292.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.24736542564138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.2037568309999997

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705356554483

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7580100340749988

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
84.63119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000554
     RDKit          3D
Dihydroandrosterone
 53 56  0  0  0  0  0  0  0  0999 V2000
    2.9360   -0.4092   -1.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -0.3349   -0.2686 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1180   -1.5478    0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995   -1.6573   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.4452    0.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5585    0.7625   -0.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2552    2.0103   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    1.7851   -0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    0.6915   -0.2246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6856    0.5159   -0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.4977    0.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5302    0.1100    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485   -1.0018    1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173   -1.5157    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373   -0.5990   -0.2168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6379   -1.3215   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    0.8665    0.1416 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7461    1.9957   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412    1.5558    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    0.0511    0.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1105   -0.6079   -0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5994   -1.3806   -2.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.4223   -2.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -0.3386   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983   -1.5601    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -2.4423   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2571   -2.6003    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733   -1.6522   -1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -0.2974    1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575    0.5367   -1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2674    2.8391   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    2.2384    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    2.6691   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.4007   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    1.0479    0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156    0.2598   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1942    1.5208   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7905   -1.3500   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5674    1.0712    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028   -1.8685    1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201   -0.2517    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -1.6126    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -2.5516    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832   -0.7621   -2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294   -1.5310   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825   -2.3283   -1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.8287    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    2.9611    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280    2.2086   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551    2.0134    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229    1.8692   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0570   -0.2283    1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598   -1.5380   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  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  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  1
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  1
 21 53  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5a-Androstane-3a,17b-diol.mol                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.852  -2.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.852  -0.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.519   0.185   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.519  -2.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.185  -2.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.149  -2.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.483  -2.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -0.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.816   0.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.281  -0.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.186   0.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.281   2.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.816   1.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.816   3.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.483   2.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.149   1.725   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.149   0.185   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.185  -0.585   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.185   0.955   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.186  -2.895   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.757   3.665   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -1.185  -3.665   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.149  -1.355   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.483   0.955   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.816  -1.355   0.000  0.00  0.00           H+0
CONECT    1    2    4   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2   18                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   18   22                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17   24                                             
CONECT    9    8   10   13   25                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12    9   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18   23                                             
CONECT   18   17    3    5   19                                             
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21   12                                                            
CONECT   22    5                                                            
CONECT   23   17                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000554
HETATM    1  C1  UNL     1       2.936  -0.409  -1.759  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.752  -0.335  -0.269  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.118  -1.548   0.312  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.699  -1.657  -0.204  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.119  -0.445   0.189  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.558   0.762  -0.475  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.255   2.010  -0.277  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.587   1.785  -1.000  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.299   0.692  -0.225  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.686   0.516  -0.747  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.408  -0.498   0.105  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.530   0.110   0.685  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.548  -1.002   1.229  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.217  -1.516   0.795  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.537  -0.599  -0.217  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.638  -1.322  -1.561  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.897   0.867   0.142  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.746   1.996  -0.282  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.141   1.556   0.168  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.060   0.051   0.348  1.00  0.00           C  
HETATM   21  O2  UNL     1       5.111  -0.608  -0.272  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.599  -1.381  -2.192  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.451   0.422  -2.307  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.028  -0.339  -2.040  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.198  -1.560   1.397  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.662  -2.442  -0.096  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.257  -2.600   0.166  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.773  -1.652  -1.325  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.003  -0.297   1.286  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.557   0.537  -1.557  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.267   2.839  -0.754  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.457   2.238   0.786  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.225   2.669  -0.987  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.389   1.401  -2.016  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.367   1.048   0.823  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.716   0.260  -1.826  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.194   1.521  -0.663  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.791  -1.350  -0.490  1.00  0.00           H  
HETATM   39  H18 UNL     1      -5.567   1.071   0.548  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.103  -1.868   1.687  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.420  -0.252   2.035  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.584  -1.613   1.721  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.322  -2.552   0.408  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.183  -0.762  -2.377  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.729  -1.531  -1.745  1.00  0.00           H  
HETATM   46  H25 UNL     1      -1.182  -2.328  -1.395  1.00  0.00           H  
HETATM   47  H26 UNL     1       1.821   0.829   1.232  1.00  0.00           H  
HETATM   48  H27 UNL     1       2.501   2.961   0.226  1.00  0.00           H  
HETATM   49  H28 UNL     1       2.728   2.209  -1.362  1.00  0.00           H  
HETATM   50  H29 UNL     1       4.355   2.013   1.174  1.00  0.00           H  
HETATM   51  H30 UNL     1       4.923   1.869  -0.527  1.00  0.00           H  
HETATM   52  H31 UNL     1       4.057  -0.228   1.426  1.00  0.00           H  
HETATM   53  H32 UNL     1       4.860  -1.538  -0.502  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   15   35
CONECT   10   11   36   37
CONECT   11   12   13   38
CONECT   12   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16
CONECT   16   44   45   46
CONECT   17   18   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   52
CONECT   21   53
END

HMDB0000554
     RDKit          3D
Dihydroandrosterone
 53 56  0  0  0  0  0  0  0  0999 V2000
    2.9360   -0.4092   -1.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -0.3349   -0.2686 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1180   -1.5478    0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995   -1.6573   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.4452    0.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5585    0.7625   -0.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2552    2.0103   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    1.7851   -0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    0.6915   -0.2246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6856    0.5159   -0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076   -0.4977    0.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5302    0.1100    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485   -1.0018    1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173   -1.5157    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373   -0.5990   -0.2168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6379   -1.3215   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    0.8665    0.1416 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7461    1.9957   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412    1.5558    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599    0.0511    0.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1105   -0.6079   -0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5994   -1.3806   -2.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.4223   -2.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -0.3386   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983   -1.5601    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -2.4423   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2571   -2.6003    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733   -1.6522   -1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -0.2974    1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575    0.5367   -1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2674    2.8391   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566    2.2384    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    2.6691   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.4007   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3672    1.0479    0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7156    0.2598   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1942    1.5208   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7905   -1.3500   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5674    1.0712    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028   -1.8685    1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201   -0.2517    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -1.6126    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -2.5516    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832   -0.7621   -2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294   -1.5310   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825   -2.3283   -1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.8287    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    2.9611    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280    2.2086   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3551    2.0134    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229    1.8692   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0570   -0.2283    1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8598   -1.5380   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  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  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  1
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  1
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5alpha,17beta)-Androstane-3,17-diol	ChEBI
3alpha,17beta-Dihydroxy-5alpha-androstane	ChEBI
Hombreol	ChEBI
(3a,5a,17b)-Androstane-3,17-diol	Generator
(3Α,5α,17β)-androstane-3,17-diol	Generator
3a,17b-Dihydroxy-5a-androstane	Generator
3Α,17β-dihydroxy-5α-androstane	Generator
Adiol	HMDB
Etiocholane-3a,17b-diol	HMDB
3a,5a-Tetrahydrotestosterone	HMDB
5a-Androstane-3a,17b-diol	HMDB
5alpha-Androstane-3alpha,17beta-androstanediol	HMDB
5alpha-Androstane-3alpha,17beta-diol	HMDB
Androstane-3a,17b-diol	HMDB
Etiocholane-3alpha,17beta-diol	HMDB
3a-Androstanediol	HMDB
3Α-androstanediol	HMDB
5Α-androstane-3α,17β-diol	HMDB

Chemical Formula

C₁₉H₃₂O₂

Average Molecular Weight

292.4562

Monoisotopic Molecular Weight

292.240230268

IUPAC Name

(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

Traditional Name

(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

CAS Registry Number

1852-53-5

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

CBMYJHIOYJEBSB-KHOSGYARSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
17-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

androstane-3alpha,17beta-diol (CHEBI:36713 )
C19 steroids (androgens) and derivatives (LMST02020052 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17716701)

Cellular substructure

Tissue

Epithelium

Epidermis (HMDB: HMDB0000554)

Nervous tissue

Hepatic tissue (HMDB: HMDB0000554)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000554)

Organ

Skin (HMDB: HMDB0000554)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000554)

Source

Exogenous

Exogenous (HMDB: HMDB0000554)

Food

Food (HMDB: HMDB0000554)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000554)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000554)

Molecular messenger

Hormone (HMDB: HMDB0000554)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000554)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000554)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 - 221 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.56	ALOGPS
logP	3.2	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.63 m³·mol⁻¹	ChemAxon
Polarizability	35.25 Å³	ChemAxon
Number of Rings	4	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]+	169.787	31661259
DarkChem	[M-H]-	167.553	31661259
AllCCS	[M+H]+	177.839	32859911
AllCCS	[M-H]-	179.136	32859911
DeepCCS	[M-2H]-	209.29	30932474
DeepCCS	[M+Na]+	183.754	30932474
AllCCS	[M+H]+	177.8	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.6	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	179.9	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.	5.94 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4283 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	68.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2466.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	623.2 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	599.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1114.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	449.0 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	1497.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	375.9 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	43.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroandrosterone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C	2433.3	Standard polar	33892256
Dihydroandrosterone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C	2438.1	Standard non polar	33892256
Dihydroandrosterone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C	2611.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroandrosterone,1TMS,isomer #1	C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]12	2563.9	Semi standard non polar	33892256
Dihydroandrosterone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O	2552.9	Semi standard non polar	33892256
Dihydroandrosterone,2TMS,isomer #1	C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]12	2573.3	Semi standard non polar	33892256
Dihydroandrosterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2857.1	Semi standard non polar	33892256
Dihydroandrosterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C1	2820.7	Semi standard non polar	33892256
Dihydroandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3133.6	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 - Dihydroandrosterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gi-0290000000-ef7ce05726cbec3a35bd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-2226900000-73765a85fad7c004bde8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroandrosterone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 10V, Positive-QTOF	splash10-004l-0090000000-22d60c19836ea8b4c291	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 20V, Positive-QTOF	splash10-056r-0390000000-edb0fb77b27575b4b729	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 40V, Positive-QTOF	splash10-00mk-2980000000-cd6eafa93f3164ed780a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 10V, Negative-QTOF	splash10-0006-0090000000-bc689c3cdfdf044c011e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 20V, Negative-QTOF	splash10-006x-0090000000-bfbc140857bbdb62bcff	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 40V, Negative-QTOF	splash10-06vm-1290000000-bced1e06a8686f3501af	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 10V, Positive-QTOF	splash10-002f-0090000000-36f4d97265b0d994d628	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 20V, Positive-QTOF	splash10-052b-3940000000-b87bad8b672cc5fb32b0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 40V, Positive-QTOF	splash10-0aos-3900000000-0f8ce10c286f165d6e0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 10V, Negative-QTOF	splash10-0006-0090000000-11452f48ce72555f1f28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 20V, Negative-QTOF	splash10-0006-0090000000-11452f48ce72555f1f28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroandrosterone 40V, Negative-QTOF	splash10-000l-0090000000-ac9e93370094e8aebfa1	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Epidermis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000475 (0.000352-0.000548) uM	Adult (>18 years old)	Male	Normal	17716701	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01530

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022114

KNApSAcK ID

Not Available

Chemspider ID

15039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3%CE%B1-Androstanediol

METLIN ID

5538

PubChem Compound

15818

PDB ID

Not Available

ChEBI ID

36713

Food Biomarker Ontology

Not Available

VMH ID

CE2209

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kieslich, Klaus. 5a-Androstane-3a,17b-diol. Ger. Offen. (1980), 6 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Deslypere JP, Vermeulen A: Aging and tissue androgens. J Clin Endocrinol Metab. 1981 Aug;53(2):430-4. [PubMed:7251820 ]
Rittmaster RS, Zwicker H, Thompson DL, Konok G, Norman RW: Androstanediol glucuronide production in human liver, prostate, and skin. Evidence for the importance of the liver in 5 alpha-reduced androgen metabolism. J Clin Endocrinol Metab. 1993 Apr;76(4):977-82. [PubMed:8473413 ]
Frye CA: Some rewarding effects of androgens may be mediated by actions of its 5alpha-reduced metabolite 3alpha-androstanediol. Pharmacol Biochem Behav. 2007 Feb;86(2):354-67. Epub 2006 Nov 15. [PubMed:17112575 ]
Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism. I--In the hypothalamus and in the anterior pituitary. J Steroid Biochem. 1979 Jul;11(1A):215-9. [PubMed:491592 ]
Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism--II. In the ventral prostate and in the seminal vesicles. J Steroid Biochem. 1979 Jul;11(1A):221-5. [PubMed:491593 ]
Eckstein B, Ravid R: Regulation of ovarian 17 beta-hydroxysteroid dehydrogenase activity by gonadotropin. Biochim Biophys Acta. 1980 Jan 17;627(2):165-71. [PubMed:6243214 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Showing metabocard for Dihydroandrosterone (HMDB0000554)

MOL for HMDB0000554 (Dihydroandrosterone)

3D MOL for HMDB0000554 (Dihydroandrosterone)

3D SDF for HMDB0000554 (Dihydroandrosterone)

3D-SDF for HMDB0000554 (Dihydroandrosterone)

PDB for HMDB0000554 (Dihydroandrosterone)

3D PDB for HMDB0000554 (Dihydroandrosterone)

SMILES for HMDB0000554 (Dihydroandrosterone)

INCHI for HMDB0000554 (Dihydroandrosterone)

Structure for HMDB0000554 (Dihydroandrosterone)

3D Structure for HMDB0000554 (Dihydroandrosterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra