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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:43 UTC

HMDB ID

HMDB0000493

Secondary Accession Numbers

HMDB00493

Metabolite Identification

Common Name

5alpha-Androstane-3beta,17beta-diol

Description

5alpha-Androstane-3beta,17beta-diol, also known as 5-α-androstane-3-β,17β-diol or 3beta,17beta-dihydroxy-5alpha-androstane, 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. Thus, 5alpha-androstane-3beta,17beta-diol is considered to be a steroid. Based on a literature review a significant number of articles have been published on 5alpha-Androstane-3beta,17beta-diol.

Structure

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


  Mrv1652310181922522D          

 25 28  0  0  0  0            999 V2000
 9999.308010000.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445010001.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4450 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1715 9998.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9997.9063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.732310000.3854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5965 9999.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5965 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3071 9999.5578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3071 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0216 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7361 9998.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.733610001.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019110000.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0191 9999.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7336 9999.5641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.232710001.0566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.448110000.8016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4481 9999.9766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2327 9999.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.717610000.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.487710001.8412    0.0000 O   0  0  0  0  0  0  0  0  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  1  0  0  0
 10  4  1  1  0  0  0
 11 13  1  0  0  0  0
 13  5  1  6  0  0  0
  8 12  1  0  0  0  0
 12  1  1  1  0  0  0
 18 12  1  0  0  0  0
 18  7  1  6  0  0  0
 15 19  1  0  0  0  0
 19  6  1  1  0  0  0
 19 22  1  0  0  0  0
 22  3  1  6  0  0  0
 16 21  1  0  0  0  0
 21  2  1  1  0  0  0
M  END

HMDB0000493
     RDKit          3D
5alpha-Androstane-3beta,17beta-diol
 53 56  0  0  0  0  0  0  0  0999 V2000
   -2.7557   -0.2502    1.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6953   -0.5109    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9821   -1.7741   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277   -1.6655    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -0.4821   -0.4808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6254    0.7494   -0.0114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0371    2.0290   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    2.0256    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856    0.9293   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6398    0.8899   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718   -0.0597   -0.9963 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6262   -0.3300   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -1.3561   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -1.3043   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825   -0.4235   -0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0190   -1.0380    1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9946    0.6197   -0.5611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9097    1.7518   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    1.1131   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0705   -0.3868   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0613   -0.8764    0.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7654   -0.5999    2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219   -0.8076    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.8103    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -2.0009   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4210   -2.6086    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -2.6111   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3716   -1.5280    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131   -0.6076   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6245    0.7023    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    2.0184   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752    2.8623   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533    2.9652    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783    1.8365    1.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266    1.1772   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8110    0.7445    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477    1.9221   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331    0.4638   -1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668   -0.3853    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992   -1.7534   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -2.1614   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8827   -0.8819   -2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -2.3262   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -1.1710    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879   -2.0653    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -0.4638    1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    0.3221   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275    2.4977   -1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307    2.3118    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5700    1.2635   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.5113    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.9277   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7074   -0.1596    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1
  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  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 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  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  6
 21 53  1  0
M  END


  Mrv1652310181922522D          

 25 28  0  0  0  0            999 V2000
 9999.308010000.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445010001.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4450 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1715 9998.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9997.9063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.732310000.3854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9999.1515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5965 9999.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8820 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5965 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3071 9999.5578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3071 9998.7327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0216 9998.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7361 9998.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.733610001.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019110000.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0191 9999.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7336 9999.5641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.232710001.0566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.448110000.8016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4481 9999.9766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2327 9999.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.717610000.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.487710001.8412    0.0000 O   0  0  0  0  0  0  0  0  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  1  0  0  0
 10  4  1  1  0  0  0
 11 13  1  0  0  0  0
 13  5  1  6  0  0  0
  8 12  1  0  0  0  0
 12  1  1  1  0  0  0
 18 12  1  0  0  0  0
 18  7  1  6  0  0  0
 15 19  1  0  0  0  0
 19  6  1  1  0  0  0
 19 22  1  0  0  0  0
 22  3  1  6  0  0  0
 16 21  1  0  0  0  0
 21  2  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000493

> <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-YSZCXEEOSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.4562

> <EXACT_MASS>
292.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.56109148865969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,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,5S,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

$$$$

HMDB0000493
     RDKit          3D
5alpha-Androstane-3beta,17beta-diol
 53 56  0  0  0  0  0  0  0  0999 V2000
   -2.7557   -0.2502    1.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6953   -0.5109    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9821   -1.7741   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277   -1.6655    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -0.4821   -0.4808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6254    0.7494   -0.0114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0371    2.0290   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    2.0256    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856    0.9293   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6398    0.8899   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718   -0.0597   -0.9963 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6262   -0.3300   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -1.3561   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -1.3043   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825   -0.4235   -0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0190   -1.0380    1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9946    0.6197   -0.5611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9097    1.7518   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    1.1131   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0705   -0.3868   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0613   -0.8764    0.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7654   -0.5999    2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219   -0.8076    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.8103    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -2.0009   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4210   -2.6086    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -2.6111   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3716   -1.5280    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131   -0.6076   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6245    0.7023    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    2.0184   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752    2.8623   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533    2.9652    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783    1.8365    1.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266    1.1772   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8110    0.7445    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477    1.9221   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331    0.4638   -1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668   -0.3853    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992   -1.7534   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -2.1614   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8827   -0.8819   -2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -2.3262   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -1.1710    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879   -2.0653    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -0.4638    1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    0.3221   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275    2.4977   -1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307    2.3118    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5700    1.2635   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.5113    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.9277   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7074   -0.1596    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1
  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  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 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  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  6
 21 53  1  0
M  END

HEADER    PROTEIN                                 18-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-19         0                                  
HETATM    1  C   UNK     0    8665.3758667.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3648669.709   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.3648665.083   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.3878663.525   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8665.3758662.758   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8668.0348667.386   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.7078665.083   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8664.0478666.611   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7138665.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.7138664.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0478663.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3738665.841   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3738664.301   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.7078663.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.0418664.301   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.0368668.933   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.7028668.163   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.7028666.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.0368665.853   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.8348668.639   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3708668.163   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.3708666.623   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.8348666.147   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.7408667.393   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8671.3108670.104   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   10                                                            
CONECT    5   13                                                            
CONECT    6   19                                                            
CONECT    7   18                                                            
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    4                                                  
CONECT   11   10   13                                                       
CONECT   12   13    8    1   18                                             
CONECT   13   12   14   11    5                                             
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16   17   21                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12    7                                             
CONECT   19   18   15    6   22                                             
CONECT   20   21   24   25                                                  
CONECT   21   20   22   16    2                                             
CONECT   22   21   23   19    3                                             
CONECT   23   22   24                                                       
CONECT   24   20   23                                                       
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000493
HETATM    1  C1  UNL     1      -2.756  -0.250   1.665  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.695  -0.511   0.181  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.982  -1.774  -0.150  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.528  -1.665   0.206  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.118  -0.482  -0.481  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.625   0.749  -0.011  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.037   2.029  -0.406  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.430   2.026   0.239  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.186   0.929  -0.468  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.640   0.890  -0.120  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.372  -0.060  -0.996  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.626  -0.330  -0.400  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.708  -1.356  -1.250  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.220  -1.304  -1.377  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.582  -0.423  -0.298  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.019  -1.038   1.036  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.995   0.620  -0.561  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.910   1.752  -0.375  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.288   1.113  -0.559  1.00  0.00           C  
HETATM   20  C19 UNL     1      -4.070  -0.387  -0.377  1.00  0.00           C  
HETATM   21  O2  UNL     1      -5.061  -0.876   0.440  1.00  0.00           O  
HETATM   22  H1  UNL     1      -3.765  -0.600   2.014  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.022  -0.808   2.250  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.691   0.810   1.931  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.069  -2.001  -1.214  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.421  -2.609   0.447  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.040  -2.611  -0.126  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.372  -1.528   1.293  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.113  -0.608  -1.579  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.625   0.702   1.106  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.213   2.018  -1.507  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.575   2.862  -0.070  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.953   2.965   0.063  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.278   1.836   1.305  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.127   1.177  -1.569  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.811   0.745   0.968  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.048   1.922  -0.334  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.633   0.464  -1.959  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.467  -0.385   0.571  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.099  -1.753  -2.232  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.961  -2.161  -0.514  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.883  -0.882  -2.348  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.819  -2.326  -1.283  1.00  0.00           H  
HETATM   44  H23 UNL     1       3.116  -1.171   1.057  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.588  -2.065   1.113  1.00  0.00           H  
HETATM   46  H25 UNL     1       1.623  -0.464   1.894  1.00  0.00           H  
HETATM   47  H26 UNL     1      -1.981   0.322  -1.627  1.00  0.00           H  
HETATM   48  H27 UNL     1      -2.727   2.498  -1.203  1.00  0.00           H  
HETATM   49  H28 UNL     1      -2.831   2.312   0.556  1.00  0.00           H  
HETATM   50  H29 UNL     1      -4.570   1.264  -1.627  1.00  0.00           H  
HETATM   51  H30 UNL     1      -5.025   1.511   0.138  1.00  0.00           H  
HETATM   52  H31 UNL     1      -4.112  -0.928  -1.345  1.00  0.00           H  
HETATM   53  H32 UNL     1      -5.707  -0.160   0.725  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

HMDB0000493
     RDKit          3D
5alpha-Androstane-3beta,17beta-diol
 53 56  0  0  0  0  0  0  0  0999 V2000
   -2.7557   -0.2502    1.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6953   -0.5109    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9821   -1.7741   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277   -1.6655    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -0.4821   -0.4808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6254    0.7494   -0.0114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0371    2.0290   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    2.0256    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856    0.9293   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6398    0.8899   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3718   -0.0597   -0.9963 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6262   -0.3300   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -1.3561   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -1.3043   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825   -0.4235   -0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0190   -1.0380    1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9946    0.6197   -0.5611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9097    1.7518   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    1.1131   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0705   -0.3868   -0.3765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0613   -0.8764    0.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7654   -0.5999    2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219   -0.8076    2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906    0.8103    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -2.0009   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4210   -2.6086    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -2.6111   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3716   -1.5280    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131   -0.6076   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6245    0.7023    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    2.0184   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752    2.8623   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533    2.9652    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783    1.8365    1.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1266    1.1772   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8110    0.7445    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477    1.9221   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331    0.4638   -1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668   -0.3853    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992   -1.7534   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -2.1614   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8827   -0.8819   -2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -2.3262   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -1.1710    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5879   -2.0653    1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -0.4638    1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    0.3221   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275    2.4977   -1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307    2.3118    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5700    1.2635   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.5113    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.9277   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7074   -0.1596    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1
  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  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 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  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  6
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,5alpha,17beta)-Androstane-3,17-diol	ChEBI
3beta,17beta-Dihydroxy-5alpha-androstane	ChEBI
5-ALPHA-ANDROSTANE-3-BETA,17BETA-diol	ChEBI
5alpha-Androstan-3beta,17beta-diol	ChEBI
(3b,5a,17b)-Androstane-3,17-diol	Generator
(3Β,5α,17β)-androstane-3,17-diol	Generator
3b,17b-Dihydroxy-5a-androstane	Generator
3Β,17β-dihydroxy-5α-androstane	Generator
5-a-ANDROSTANE-3-b,17b-diol	Generator
5-Α-androstane-3-β,17β-diol	Generator
5a-Androstan-3b,17b-diol	Generator
5Α-androstan-3β,17β-diol	Generator
5a-Androstane-3b,17b-diol	Generator
5Α-androstane-3β,17β-diol	Generator
3b,17b-Androstanediol	HMDB
3b-Androstanediol	HMDB
3Β-androstanediol	HMDB
5alpha-Androstane-3beta,17beta-diol	HMDB

Chemical Formula

C₁₉H₃₂O₂

Average Molecular Weight

292.4562

Monoisotopic Molecular Weight

292.240230268

IUPAC Name

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

CAS Registry Number

571-20-0

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-YSZCXEEOSA-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-beta-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

3beta-hydroxy steroid (CHEBI:18329 )
17beta-hydroxy steroid (CHEBI:18329 )
androstane-3,17-diol (CHEBI:18329 )
C19 steroids (androgens) and derivatives (C12525 )
C19 steroids (androgens) and derivatives (LMST02020053 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000493)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17716701)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000493)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000493)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000493)

Source

Exogenous

Exogenous (HMDB: HMDB0000493)

Food

Food (HMDB: HMDB0000493)

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: HMDB0000493)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000493)

Molecular messenger

Hormone (HMDB: HMDB0000493)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000493)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000493)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3 mg/mL	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	35.56 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]+	168.854	31661259
DarkChem	[M-H]-	164.972	31661259
AllCCS	[M+H]+	177.839	32859911
AllCCS	[M-H]-	179.136	32859911
DeepCCS	[M-2H]-	206.069	30932474
DeepCCS	[M+Na]+	180.618	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.	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
5alpha-Androstane-3beta,17beta-diol	[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
5alpha-Androstane-3beta,17beta-diol	[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
5alpha-Androstane-3beta,17beta-diol	[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
5alpha-Androstane-3beta,17beta-diol,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
5alpha-Androstane-3beta,17beta-diol,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
5alpha-Androstane-3beta,17beta-diol,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
5alpha-Androstane-3beta,17beta-diol,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
5alpha-Androstane-3beta,17beta-diol,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
5alpha-Androstane-3beta,17beta-diol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C1	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 - 5alpha-Androstane-3beta,17beta-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gj-0290000000-f3f7878ea28711151686	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-2226900000-73765a85fad7c004bde8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0feb-0910000000-95c33219e21fca1431b4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-006t-9621000000-2bf4147f35ce4e2b858a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0aos-9851000000-65b418ed0598e7d18552	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Positive-QTOF	splash10-004l-0090000000-22d60c19836ea8b4c291	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Positive-QTOF	splash10-056r-0390000000-edb0fb77b27575b4b729	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Positive-QTOF	splash10-00mk-2980000000-cd6eafa93f3164ed780a	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Negative-QTOF	splash10-0006-0090000000-bc689c3cdfdf044c011e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Negative-QTOF	splash10-006x-0090000000-bfbc140857bbdb62bcff	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Negative-QTOF	splash10-06vm-1290000000-bced1e06a8686f3501af	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Positive-QTOF	splash10-002f-0090000000-36f4d97265b0d994d628	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Positive-QTOF	splash10-052b-3940000000-b87bad8b672cc5fb32b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Positive-QTOF	splash10-0aos-3900000000-0f8ce10c286f165d6e0f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Negative-QTOF	splash10-0006-0090000000-11452f48ce72555f1f28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Negative-QTOF	splash10-0006-0090000000-11452f48ce72555f1f28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Negative-QTOF	splash10-000l-0090000000-ac9e93370094e8aebfa1	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000149 (0.000057-0.00025) uM	Adult (>18 years old)	Male	Normal	17716701	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

DB03882

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022073

KNApSAcK ID

Not Available

Chemspider ID

211834

KEGG Compound ID

C12525

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3β-Androstanediol

METLIN ID

5479

PubChem Compound

242332

PDB ID

Not Available

ChEBI ID

18329

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Merlani, M. I.; Amiranashvili, L. Sh.; Men'shova, N. I.; Kemertelidze, E. P. Synthesis of 5a-androstan-3b,17b-diol from tigogenin. Chemistry of Natural Compounds (2007), 43(1), 97-99.

Material Safety Data Sheet (MSDS)

Not Available

General References

Stewart ME, Pochi PE, Strauss JS, Wotiz HH, Clark SJ: In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol. J Endocrinol. 1977 Mar;72(3):385-90. [PubMed:856929 ]
Guerini V, Sau D, Scaccianoce E, Rusmini P, Ciana P, Maggi A, Martini PG, Katzenellenbogen BS, Martini L, Motta M, Poletti A: The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype. Cancer Res. 2005 Jun 15;65(12):5445-53. [PubMed:15958594 ]

Showing metabocard for 5alpha-Androstane-3beta,17beta-diol (HMDB0000493)

MOL for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

3D MOL for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

3D SDF for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

3D-SDF for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

PDB for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

3D PDB for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

SMILES for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

INCHI for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

Structure for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

3D Structure for HMDB0000493 (5alpha-Androstane-3beta,17beta-diol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra