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enzymes (1) Show 1 protein

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

HMDB0000495

Secondary Accession Numbers

HMDB00495

Metabolite Identification

Common Name

Androstanediol

Description

Androstanediol is a metabolite of dihydrotestosterone, itself a metabolite of testosterone. Androstanediol is implicated in the regulation of gonadotropin secretion. As a metabolite of dihydroxytestosterone formed in the peripheral tissues, androstanediol and androstnediol-glucuronide can be used to estimate peripheral androgen activity. Androstanediol is a potential GABA (A) receptor-modulating neurosteroid with anticonvulsant properties and hence could act as a key neuromodulator in the central nervous system. It is considered that androstanediol has hedonic effects; therefore it is anticipated that androgens that are readily metabolized to androstanediol may have higher abuse potential than androgens that are not as easily metabolized to androstanediol. These results add to the growing literature indicating that athletes and non-athletes may be at considerable risk when they abuse androgens. (PMID: 11500254 , 16040068 , 11744084 ).

Structure

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


  Mrv0541 02231218332D          

 25 28  0  0  1  0            999 V2000
   23.0815  -14.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0815  -15.0231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.7960  -15.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5105  -15.0231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.5105  -14.1981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.7960  -13.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -15.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -15.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -14.1981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2249  -13.7856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.6539  -13.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6539  -12.9606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.9394  -12.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -12.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4385  -14.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9235  -13.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4385  -12.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3670  -15.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7401  -12.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6935  -11.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -14.6106    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5105  -13.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -13.3731    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.7401  -14.6061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5302  -15.8676    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  6  0  0  0
M  END

HMDB0000495
     RDKit          3D
Androstanediol
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.1633    1.3205   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7541    0.0204   -0.0063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2694    0.1578    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    0.8022    1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0540    0.0324    0.5969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420    0.1032   -0.8346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5341   -0.4784   -1.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -0.1065   -1.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996   -0.4577   -0.1354 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7662   -0.3243    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1933    0.2458    1.3545 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4549   -0.3005    1.6629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -0.1788    2.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379    0.2140    2.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779    0.4298    0.7599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6847    1.8977    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818   -0.6990   -0.8388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3882   -0.8852   -2.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885   -1.2851   -1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -0.9662   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0984   -0.4903    0.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5065    1.6652   -1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943    1.2548   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654    2.1053    0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766   -0.7913    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743    0.8478    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    0.7161    2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    1.8660    1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0269   -1.0468    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596    1.1728   -1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.0982   -2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.5865   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.7460   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.9388   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -1.5023    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2459    0.2636   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -1.3567   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    1.3460    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4016   -1.2917    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -1.2798    2.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    0.3009    3.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -0.6109    2.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393    1.1308    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    2.3155   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    2.4961    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546    2.0954   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969   -1.6651   -0.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109    0.0529   -2.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.6797   -2.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9018   -2.4036   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5690   -0.7790   -2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244   -1.8760    0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3747   -0.9063    1.0682 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  0
 21 53  1  0
M  END


  Mrv0541 02231218332D          

 25 28  0  0  1  0            999 V2000
   23.0815  -14.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0815  -15.0231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.7960  -15.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5105  -15.0231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.5105  -14.1981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.7960  -13.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -15.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -15.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -14.1981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2249  -13.7856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.6539  -13.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6539  -12.9606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.9394  -12.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -12.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4385  -14.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9235  -13.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4385  -12.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3670  -15.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7401  -12.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6935  -11.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -14.6106    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5105  -13.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -13.3731    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.7401  -14.6061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5302  -15.8676    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000495

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(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-UNPXRYTGSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.4562

> <EXACT_MASS>
292.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.34320962303727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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>
84.63119999999998

> <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,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000495
     RDKit          3D
Androstanediol
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.1633    1.3205   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7541    0.0204   -0.0063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2694    0.1578    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    0.8022    1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0540    0.0324    0.5969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420    0.1032   -0.8346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5341   -0.4784   -1.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -0.1065   -1.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996   -0.4577   -0.1354 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7662   -0.3243    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1933    0.2458    1.3545 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4549   -0.3005    1.6629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -0.1788    2.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379    0.2140    2.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779    0.4298    0.7599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6847    1.8977    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818   -0.6990   -0.8388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3882   -0.8852   -2.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885   -1.2851   -1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -0.9662   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0984   -0.4903    0.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5065    1.6652   -1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943    1.2548   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654    2.1053    0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766   -0.7913    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743    0.8478    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    0.7161    2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    1.8660    1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0269   -1.0468    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596    1.1728   -1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.0982   -2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.5865   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.7460   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.9388   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -1.5023    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2459    0.2636   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -1.3567   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    1.3460    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4016   -1.2917    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -1.2798    2.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    0.3009    3.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -0.6109    2.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393    1.1308    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    2.3155   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    2.4961    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546    2.0954   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969   -1.6651   -0.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109    0.0529   -2.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.6797   -2.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9018   -2.4036   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5690   -0.7790   -2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244   -1.8760    0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3747   -0.9063    1.0682 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  0
 21 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      43.085 -26.503   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.085 -28.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      44.419 -28.813   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      45.753 -28.043   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.753 -26.503   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      44.419 -25.733   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.086 -28.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.420 -28.043   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.420 -26.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.086 -25.733   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.754 -25.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.754 -24.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      48.420 -23.423   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      47.086 -24.193   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.219 -26.209   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.124 -24.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      51.219 -23.717   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      41.752 -28.813   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      49.915 -22.662   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      51.695 -22.253   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      47.086 -27.273   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      45.753 -24.963   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      48.420 -24.963   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      49.915 -27.265   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      45.790 -29.620   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   25                                             
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20                                                  
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000495
HETATM    1  C1  UNL     1      -3.163   1.320  -0.626  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.754   0.020  -0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.269   0.158   1.408  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.906   0.802   1.452  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.054   0.032   0.597  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.442   0.103  -0.835  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.534  -0.478  -1.817  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.954  -0.107  -1.565  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.300  -0.458  -0.135  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.766  -0.324   0.046  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.193   0.246   1.355  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.455  -0.300   1.663  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.252  -0.179   2.432  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.838   0.214   2.218  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.478   0.430   0.760  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.685   1.898   0.450  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.682  -0.699  -0.839  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.388  -0.885  -2.110  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.788  -1.285  -1.661  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.863  -0.966  -0.180  1.00  0.00           C  
HETATM   21  O2  UNL     1      -5.098  -0.490   0.197  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.507   1.665  -1.432  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.194   1.255  -1.082  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.265   2.105   0.164  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.277  -0.791   1.940  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.974   0.848   1.932  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.549   0.716   2.511  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.934   1.866   1.205  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.027  -1.047   0.919  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.560   1.173  -1.075  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.250  -0.098  -2.826  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.455  -1.586  -1.873  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.594  -0.746  -2.210  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.199   0.939  -1.825  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.929  -1.502   0.026  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.246   0.264  -0.789  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.214  -1.357  -0.053  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.349   1.346   1.326  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.402  -1.292   1.478  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.389  -1.280   2.607  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.601   0.301   3.392  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.191  -0.611   2.639  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.539   1.131   2.770  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.779   2.316  -0.031  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.829   2.496   1.392  1.00  0.00           H  
HETATM   46  H25 UNL     1       2.555   2.095  -0.180  1.00  0.00           H  
HETATM   47  H26 UNL     1      -1.497  -1.665  -0.350  1.00  0.00           H  
HETATM   48  H27 UNL     1      -2.511   0.053  -2.688  1.00  0.00           H  
HETATM   49  H28 UNL     1      -1.910  -1.680  -2.716  1.00  0.00           H  
HETATM   50  H29 UNL     1      -3.902  -2.404  -1.754  1.00  0.00           H  
HETATM   51  H30 UNL     1      -4.569  -0.779  -2.243  1.00  0.00           H  
HETATM   52  H31 UNL     1      -3.624  -1.876   0.437  1.00  0.00           H  
HETATM   53  H32 UNL     1      -5.375  -0.906   1.068  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

HMDB0000495
     RDKit          3D
Androstanediol
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.1633    1.3205   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7541    0.0204   -0.0063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2694    0.1578    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056    0.8022    1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0540    0.0324    0.5969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420    0.1032   -0.8346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5341   -0.4784   -1.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -0.1065   -1.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996   -0.4577   -0.1354 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7662   -0.3243    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1933    0.2458    1.3545 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4549   -0.3005    1.6629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -0.1788    2.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379    0.2140    2.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4779    0.4298    0.7599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6847    1.8977    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818   -0.6990   -0.8388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3882   -0.8852   -2.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885   -1.2851   -1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -0.9662   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0984   -0.4903    0.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5065    1.6652   -1.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943    1.2548   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654    2.1053    0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2766   -0.7913    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743    0.8478    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    0.7161    2.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    1.8660    1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0269   -1.0468    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596    1.1728   -1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.0982   -2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.5865   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.7460   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.9388   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -1.5023    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2459    0.2636   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -1.3567   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    1.3460    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4016   -1.2917    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -1.2798    2.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    0.3009    3.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -0.6109    2.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393    1.1308    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    2.3155   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8285    2.4961    1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546    2.0954   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969   -1.6651   -0.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109    0.0529   -2.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.6797   -2.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9018   -2.4036   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5690   -0.7790   -2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244   -1.8760    0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3747   -0.9063    1.0682 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  0
 21 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Androstane-3,17-diol	KEGG
3-a-Androstanediol	HMDB
3-alpha-Androstanediol	HMDB
3alpha-Androstanediol	HMDB
5 a-Androstane-3 a, 17 b-diol	HMDB
5 alpha-Androstane-3 alpha, 17 beta-diol	HMDB
5-a-Androstane-3-a, 17-b-diol	HMDB
5-alpha-Androstan-3-alpha,17-beta-diol	HMDB
5-alpha-Androstane-3-a, 17-beta-diol	HMDB
5-alpha-Androstane-3-alpha-17-beta-diol	HMDB
5 Androstane 3,17 diol	MeSH, HMDB
5 alpha Androstane 3 alpha,17 beta diol	MeSH, HMDB
5 alpha Androstane 3 beta,17 alpha diol	MeSH, HMDB
5 alpha Androstane 3 beta,17 beta diol	MeSH, HMDB
5 alpha Androstane 3alpha,17 beta diol	MeSH, HMDB
5 alpha-Androstane-3 alpha,17 beta-diol	MeSH, HMDB
5 alpha-Androstane-3 beta,17 alpha-diol	MeSH, HMDB
5 alpha-Androstane-3 beta,17 beta-diol	MeSH, HMDB
5 alpha-Androstane-3alpha,17 beta-diol	MeSH, HMDB
5 beta Androstane 3 alpha,17 beta diol	MeSH, HMDB
5 beta-Androstane-3 alpha,17 beta-diol	MeSH, HMDB
5-Androstane-3,17-diol	MeSH, HMDB
5alpha Androstane 3beta,17alpha diol	MeSH, HMDB
5alpha-Androstane-3beta,17alpha-diol	MeSH, HMDB
Androstane 3,17 diol	MeSH, HMDB

Chemical Formula

C₁₉H₃₂O₂

Average Molecular Weight

292.4562

Monoisotopic Molecular Weight

292.240230268

IUPAC Name

(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

Traditional Name

(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

CAS Registry Number

25126-76-5

SMILES

[H][C@@]12CCC(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-UNPXRYTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0000495)
Extracellular (HMDB: HMDB0000495)

Biofluid or Excreta

Excreta

Urine (PMID: 6180540)

Non-excretory biofluid

Blood (HMDB: HMDB0000495)

Blood (HMDB: HMDB0000495)
Urine (HMDB: HMDB0000495)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000495)

Organ

Testis (HMDB: HMDB0000495)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000495)

Source

Endogenous

Endogenous (HMDB: HMDB0000495)

Animal

Animal (HMDB: HMDB0000495)

Exogenous

Food

Food (HMDB: HMDB0000495)

Animal origin

Lagomorph

Poultry

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

Bovine

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Venison

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

Swine

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

Caprae

Domestic goat (FooDB: FOOD00529)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Prostate cancer (HMDB: HMDB0000495)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000495)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000495)

Cellular process

Cell signaling (HMDB: HMDB0000495)

System process

Reproduction (HMDB: HMDB0000495)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000495)

Molecular messenger

Hormone (HMDB: HMDB0000495)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000495)

Emulsifier (HMDB: HMDB0000495)

Pharmaceutical industry

Biomarker

Prostate cancer (MarkerDB: MDB00000176)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	35.34 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]+	170.663	31661259
DarkChem	[M-H]-	166.247	31661259
AllCCS	[M+H]+	177.839	32859911
AllCCS	[M-H]-	179.136	32859911
DeepCCS	[M-2H]-	206.369	30932474
DeepCCS	[M+Na]+	181.627	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Androstanediol	[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C	2444.0	Standard polar	33892256
Androstanediol	[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C	2471.5	Standard non polar	33892256
Androstanediol	[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C	2611.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Androstanediol,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@@]43C)[C@@H]1CCC2O[Si](C)(C)C	2596.8	Semi standard non polar	33892256
Androstanediol,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]1CCC2O	2582.8	Semi standard non polar	33892256
Androstanediol,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2O[Si](C)(C)C	2601.9	Semi standard non polar	33892256
Androstanediol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2876.1	Semi standard non polar	33892256
Androstanediol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(O)[C@@]4(C)CC[C@@H]32)C1	2839.6	Semi standard non polar	33892256
Androstanediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC[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	3155.6	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 - Androstanediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gi-0290000000-ef7ce05726cbec3a35bd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-2237900000-35be1627cada18777db8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstanediol 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 - Androstanediol 10V, Positive-QTOF	splash10-004l-0090000000-22d60c19836ea8b4c291	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 20V, Positive-QTOF	splash10-056r-0390000000-edb0fb77b27575b4b729	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 40V, Positive-QTOF	splash10-00mk-2980000000-cd6eafa93f3164ed780a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 10V, Negative-QTOF	splash10-0006-0090000000-bc689c3cdfdf044c011e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 20V, Negative-QTOF	splash10-006x-0090000000-bfbc140857bbdb62bcff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 40V, Negative-QTOF	splash10-06vm-1290000000-bced1e06a8686f3501af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 10V, Negative-QTOF	splash10-0006-0090000000-11452f48ce72555f1f28	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 20V, Negative-QTOF	splash10-0006-0090000000-11452f48ce72555f1f28	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 40V, Negative-QTOF	splash10-000l-0090000000-ac9e93370094e8aebfa1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 10V, Positive-QTOF	splash10-002f-0090000000-36f4d97265b0d994d628	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 20V, Positive-QTOF	splash10-052b-3940000000-b87bad8b672cc5fb32b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstanediol 40V, Positive-QTOF	splash10-0aos-3900000000-0f8ce10c286f165d6e0f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.022 +/- 0.0043 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	6180540	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.019 +/- 0.0029 umol/mmol creatinine	Adult (>18 years old)	Both	Benign prostatic hypertrophy (BPH)	6180540	details
Urine	Detected and Quantified	0.10 +/- 0.04 umol/mmol creatinine	Adult (>18 years old)	Both	Prostate cancer	6180540	details

Associated Disorders and Diseases

Disease References

Benign prostatic hyperplasia
Puah CM, Williams G, Ghanadian R: Urinary unconjugated 5 alpha-androstane-3 alpha, 17 beta-diol in patients with prostatic tumours. Urol Res. 1982;10(2):81-4. [PubMed:6180540 ]
Prostate cancer
Puah CM, Williams G, Ghanadian R: Urinary unconjugated 5 alpha-androstane-3 alpha, 17 beta-diol in patients with prostatic tumours. Urol Res. 1982;10(2):81-4. [PubMed:6180540 ]

Associated OMIM IDs

600082 (Benign prostatic hyperplasia)
176807 (Prostate cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB025706

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000176

Good Scents ID

Not Available

References

Synthesis Reference

Vierhapper H Formation of androstanediol from 13C-labeled testosterone in humans. Steroids (1990), 55(4), 177-80.

Material Safety Data Sheet (MSDS)

Not Available

General References

Chetyrkin SV, Hu J, Gough WH, Dumaual N, Kedishvili NY: Further characterization of human microsomal 3alpha-hydroxysteroid dehydrogenase. Arch Biochem Biophys. 2001 Feb 1;386(1):1-10. [PubMed:11360992 ]
Karlsson T, Vahlquist A, Kedishvili N, Torma H: 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8. [PubMed:12646198 ]
Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]
Gupta MK, Guryev OL, Auchus RJ: 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. [PubMed:14522586 ]
Secreto G, Toniolo P, Berrino F, Recchione C, Cavalleri A, Pisani P, Totis A, Fariselli G, Di Pietro S: Serum and urinary androgens and risk of breast cancer in postmenopausal women. Cancer Res. 1991 May 15;51(10):2572-6. [PubMed:2021938 ]
Gratterola R: Anovulation and increased androgenic activity as breast cancer risk in women with fibrocystic disease of the breast. Cancer Res. 1978 Sep;38(9):3051-4. [PubMed:679211 ]
Leszczynski DE, Schafer RM: Characterization of steroid hormone association with human plasma lipoproteins. Steroids. 1989 Jul;54(1):37-53. [PubMed:2815156 ]
Thompson DL, Rittmaster RS, Rodriguez AM, Moore PH Jr, Rao PN: Synthesis of new steroid haptens for radioimmunoassay--VIII. Development and validation of a specific radioimmunoassay for serum 5 alpha-androstane-3 alpha, 17 beta-diol 17-glucuronide. J Steroid Biochem. 1990 Jul 4;36(4):345-9. [PubMed:2391963 ]
Secreto G, Toniolo P, Berrino F, Recchione C, Di Pietro S, Fariselli G, Decarli A: Increased androgenic activity and breast cancer risk in premenopausal women. Cancer Res. 1984 Dec;44(12 Pt 1):5902-5. [PubMed:6498847 ]
Ivell R, Balvers M, Anand RJ, Paust HJ, McKinnell C, Sharpe R: Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells. Endocrinology. 2003 Jul;144(7):3130-7. [PubMed:12810569 ]
Wudy SA, Dorr HG, Solleder C, Djalali M, Homoki J: Profiling steroid hormones in amniotic fluid of midpregnancy by routine stable isotope dilution/gas chromatography-mass spectrometry: reference values and concentrations in fetuses at risk for 21-hydroxylase deficiency. J Clin Endocrinol Metab. 1999 Aug;84(8):2724-8. [PubMed:10443667 ]
Keel BA, Abney TO: Oestrogenic regulation of testicular androgen production during development in the rat. J Endocrinol. 1985 May;105(2):211-8. [PubMed:2985727 ]
Klemm W, Liebich HM, Gupta D: Plasma levels of 5alpha-androstane-3alpha,17beta-diol in boys during adolescent growth. J Clin Endocrinol Metab. 1976 Mar;42(3):514-9. [PubMed:1254692 ]
Frye CA, Park D, Tanaka M, Rosellini R, Svare B: The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference. Psychoneuroendocrinology. 2001 Oct;26(7):731-50. [PubMed:11500254 ]
Reddy DS, Venkatarangan L, Chien B, Ramu K: A high-performance liquid chromatography-tandem mass spectrometry assay of the androgenic neurosteroid 3alpha-androstanediol (5alpha-androstane-3alpha,17beta-diol) in plasma. Steroids. 2005 Dec 1;70(13):879-85. Epub 2005 Jul 22. [PubMed:16040068 ]
Rosellini RA, Svare BB, Rhodes ME, Frye CA: The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference. Brain Res Brain Res Rev. 2001 Nov;37(1-3):162-71. [PubMed:11744084 ]

Enzymes

Enzyme Details

1. Retinol dehydrogenase 16

General function:: Involved in oxidoreductase activity
Specific function:: Oxidoreductase with a preference for NAD. Oxidizes all- trans-retinol and 13-cis-retinol to the corresponding aldehydes. Has higher activity towards CRBP-bound retinol than with free retinol. Oxidizes 3-alpha-hydroxysteroids. Oxidizes androstanediol and androsterone to dihydrotestosterone and androstanedione. Can also catalyze the reverse reaction
Gene Name:: RDH16
Uniprot ID:: O75452
Molecular weight:: 35673.1

Showing metabocard for Androstanediol (HMDB0000495)

MOL for HMDB0000495 (Androstanediol)

3D MOL for HMDB0000495 (Androstanediol)

3D SDF for HMDB0000495 (Androstanediol)

3D-SDF for HMDB0000495 (Androstanediol)

PDB for HMDB0000495 (Androstanediol)

3D PDB for HMDB0000495 (Androstanediol)

SMILES for HMDB0000495 (Androstanediol)

INCHI for HMDB0000495 (Androstanediol)

Structure for HMDB0000495 (Androstanediol)

3D Structure for HMDB0000495 (Androstanediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes