Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 18:04:32 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005935

Secondary Accession Numbers

HMDB0006571
HMDB05935
HMDB06571

Metabolite Identification

Common Name

Androstenol

Description

Androstenol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. Androstenol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. Androstenol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890 , 8142319 , 16415088 ). 3a-Hydroxyandrost-16-ene is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 3a-Hydroxyandrost-16-ene has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 3a-Hydroxyandrost-16-ene is structurally similar to endogenous A-ring reduced neurosteroids that act as positive modulators of GABAA receptors. 3a-Hydroxyandrost-16-ene has neurosteroid-like activity as a GABAA receptor modulator. The various actions of 3a-Hydroxyandrost-16-ene in the whole-animal models are consistent with its activity as a GABAA receptor modulator. GABAA receptors could represent a target for 3a-Hydroxyandrost-16-ene as a pheromone, for which it is well suited because of high volatility and lipophilicity, or as a conventional hormonal neurosteroid. (PMID: 1419890 , 8142319 , 16415088 ).

Structure

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

ATE
  Mrv1652304202019592D          

 25 28  0  0  0  0            999 V2000
    3.2286    0.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4165    0.3291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1362   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847    0.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.8146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5407    1.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922    0.0387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5119   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199   -0.1065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3002   -0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    0.5242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2714    1.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    0.3790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0151    0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.3969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1123   -1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687   -0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929   -0.1173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709    1.3638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.9706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    0.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 21  1  1  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 22  1  6  0  0  0
  7 13  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  6  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 24  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  6  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  1  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END

HMDB0005935
     RDKit          3D
Androstenol
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.9373   -1.5148   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -0.0748   -0.6702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2649    0.4541   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035    0.9322    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.7374    1.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    0.8133    0.3521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8724    0.3515    0.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1841    1.4583    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698    1.2279    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.7368    0.4962 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3674    0.2330    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -0.1389   -0.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3798    0.9843   -1.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -1.1294   -1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -0.7344   -1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -0.3605   -0.2224 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1519   -1.5484    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    0.2004   -0.5751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7764   -0.5646   -1.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379    0.0762   -1.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221   -1.8520    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -2.1421   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -1.7061    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    0.4489   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4427    1.3900    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -0.3001    1.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1866    1.5112    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358    1.8504   -0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716   -0.5497    1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    1.5145    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    2.4130    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    2.2168    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4566    0.5775    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235    1.5772   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260    1.0974    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705   -0.6024    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1003   -0.5957   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    1.6362   -0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -2.1628   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -1.1174   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8650    0.1115   -2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -1.6409   -1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -1.2519    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956   -2.1642    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394   -2.2499    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    1.2424   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -1.6326   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -0.4923   -2.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185    1.1544   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897   -0.4212   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  2  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
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
  6  2  1  0
 18  7  1  0
 20  2  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

ATE
  Mrv1652304202019592D          

 25 28  0  0  0  0            999 V2000
    3.2286    0.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4165    0.3291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1362   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847    0.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.8146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5407    1.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922    0.0387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5119   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199   -0.1065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3002   -0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    0.5242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2714    1.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    0.3790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0151    0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.3969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1123   -1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687   -0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929   -0.1173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709    1.3638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.9706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    0.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 21  1  1  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 22  1  6  0  0  0
  7 13  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  6  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 24  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  6  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  1  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005935

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC=C[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/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
KRVXMNNRSSQZJP-PHFHYRSDSA-N

> <FORMULA>
C19H30O

> <MOLECULAR_WEIGHT>
274.4409

> <EXACT_MASS>
274.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
33.66968019841896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol

> <ALOGPS_LOGP>
5.13

> <JCHEM_LOGP>
4.072646241333334

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.29639632111979

> <JCHEM_PKA_STRONGEST_BASIC>
-1.356956249142204

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
84.23230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0005935
     RDKit          3D
Androstenol
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.9373   -1.5148   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -0.0748   -0.6702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2649    0.4541   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035    0.9322    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.7374    1.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    0.8133    0.3521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8724    0.3515    0.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1841    1.4583    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698    1.2279    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.7368    0.4962 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3674    0.2330    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -0.1389   -0.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3798    0.9843   -1.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -1.1294   -1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -0.7344   -1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -0.3605   -0.2224 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1519   -1.5484    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    0.2004   -0.5751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7764   -0.5646   -1.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379    0.0762   -1.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221   -1.8520    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -2.1421   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -1.7061    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    0.4489   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4427    1.3900    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -0.3001    1.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1866    1.5112    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358    1.8504   -0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716   -0.5497    1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    1.5145    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    2.4130    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    2.2168    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4566    0.5775    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235    1.5772   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260    1.0974    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705   -0.6024    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1003   -0.5957   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    1.6362   -0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -2.1628   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -1.1174   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8650    0.1115   -2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -1.6409   -1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -1.2519    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956   -2.1642    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394   -2.2499    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    1.2424   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -1.6326   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -0.4923   -2.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185    1.1544   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897   -0.4212   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  2  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
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
  6  2  1  0
 18  7  1  0
 20  2  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ATE                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0       6.027   0.885   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.511   0.614   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.988  -0.834   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.472  -1.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.518   1.792   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.002   1.521   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.009   2.698   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.479   0.072   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.956  -1.376   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.037  -0.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.560  -1.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.030   0.979   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.507   2.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.546   0.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.762   1.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.069  -0.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.076  -1.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.741  -2.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.608  -0.691   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.036   0.788   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       5.213  -0.219   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.372   2.546   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.665  -1.032   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.732   1.812   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.285   1.766   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    5   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    8                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7    8   22                                             
CONECT    7    6   13                                                       
CONECT    8    4    6    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   23                                             
CONECT   11   10   17                                                       
CONECT   12   10   13   14   24                                             
CONECT   13    7   12                                                       
CONECT   14   12   15   16   25                                             
CONECT   15   14   20                                                       
CONECT   16   14   17   18   19                                             
CONECT   17   11   16                                                       
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   15   19                                                       
CONECT   21    2                                                            
CONECT   22    6                                                            
CONECT   23   10                                                            
CONECT   24   12                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0005935
HETATM    1  C1  UNL     1      -2.937  -1.515  -0.214  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.914  -0.075  -0.670  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.265   0.454  -0.644  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.503   0.932   0.571  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.277   0.737   1.440  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.229   0.813   0.352  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.872   0.352   0.710  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.184   1.458   1.494  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.270   1.228   1.696  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.007   0.737   0.496  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.367   0.233   0.855  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.131  -0.139  -0.397  1.00  0.00           C  
HETATM   13  O1  UNL     1       4.380   0.984  -1.191  1.00  0.00           O  
HETATM   14  C13 UNL     1       3.384  -1.129  -1.255  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.964  -0.734  -1.495  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.251  -0.360  -0.222  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.152  -1.548   0.720  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.087   0.200  -0.575  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.776  -0.565  -1.640  1.00  0.00           C  
HETATM   20  C19 UNL     1      -2.138   0.076  -1.939  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.022  -1.852   0.270  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.070  -2.142  -1.142  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.817  -1.706   0.406  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.956   0.449  -1.498  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.443   1.390   0.875  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.282  -0.300   1.823  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.187   1.511   2.200  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.236   1.850  -0.025  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.872  -0.550   1.333  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.674   1.515   2.496  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.409   2.413   0.981  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.727   2.217   1.980  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.457   0.578   2.596  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.123   1.577  -0.216  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.926   1.097   1.308  1.00  0.00           H  
HETATM   36  H16 UNL     1       3.371  -0.602   1.557  1.00  0.00           H  
HETATM   37  H17 UNL     1       5.100  -0.596  -0.104  1.00  0.00           H  
HETATM   38  H18 UNL     1       4.882   1.636  -0.665  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.450  -2.163  -0.899  1.00  0.00           H  
HETATM   40  H20 UNL     1       3.901  -1.117  -2.258  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.865   0.111  -2.194  1.00  0.00           H  
HETATM   42  H22 UNL     1       1.430  -1.641  -1.898  1.00  0.00           H  
HETATM   43  H23 UNL     1       1.073  -1.252   1.776  1.00  0.00           H  
HETATM   44  H24 UNL     1       2.096  -2.164   0.641  1.00  0.00           H  
HETATM   45  H25 UNL     1       0.339  -2.250   0.424  1.00  0.00           H  
HETATM   46  H26 UNL     1       0.081   1.242  -0.955  1.00  0.00           H  
HETATM   47  H27 UNL     1      -0.908  -1.633  -1.423  1.00  0.00           H  
HETATM   48  H28 UNL     1      -0.163  -0.492  -2.561  1.00  0.00           H  
HETATM   49  H29 UNL     1      -1.918   1.154  -2.114  1.00  0.00           H  
HETATM   50  H30 UNL     1      -2.590  -0.421  -2.804  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    6   20
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6   26   27
CONECT    6    7   28
CONECT    7    8   18   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   16   34
CONECT   11   12   35   36
CONECT   12   13   14   37
CONECT   13   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   18
CONECT   17   43   44   45
CONECT   18   19   46
CONECT   19   20   47   48
CONECT   20   49   50
END

HMDB0005935
     RDKit          3D
Androstenol
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.9373   -1.5148   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -0.0748   -0.6702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2649    0.4541   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035    0.9322    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.7374    1.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286    0.8133    0.3521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8724    0.3515    0.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1841    1.4583    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698    1.2279    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.7368    0.4962 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3674    0.2330    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -0.1389   -0.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3798    0.9843   -1.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -1.1294   -1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -0.7344   -1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -0.3605   -0.2224 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1519   -1.5484    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    0.2004   -0.5751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7764   -0.5646   -1.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379    0.0762   -1.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221   -1.8520    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -2.1421   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -1.7061    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    0.4489   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4427    1.3900    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -0.3001    1.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1866    1.5112    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358    1.8504   -0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716   -0.5497    1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    1.5145    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    2.4130    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    2.2168    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4566    0.5775    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235    1.5772   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260    1.0974    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705   -0.6024    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1003   -0.5957   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    1.6362   -0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -2.1628   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -1.1174   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8650    0.1115   -2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -1.6409   -1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -1.2519    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0956   -2.1642    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394   -2.2499    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    1.2424   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -1.6326   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1632   -0.4923   -2.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185    1.1544   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897   -0.4212   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  2  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
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
  6  2  1  0
 18  7  1  0
 20  2  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5alpha)-Androst-16-en-3-ol	ChEBI
3alpha-Hydroxyandrost-16-ene	ChEBI
Androst-16-en-3alpha-ol	ChEBI
(3a,5a)-Androst-16-en-3-ol	Generator
(3Α,5α)-androst-16-en-3-ol	Generator
3a-Hydroxyandrost-16-ene	Generator
3Α-hydroxyandrost-16-ene	Generator
Androst-16-en-3a-ol	Generator
Androst-16-en-3α-ol	Generator
16,17-Androstene-3-ol	HMDB
3a-Hydroxy-5a-androst-16-ene	HMDB
3a-Hydroxyandrostene	HMDB
5a-Androst-16-en-3a-ol	HMDB
5alpha-Androst-16-en-3alpha-ol	HMDB
Androst-16-en-3-ol	HMDB
5 alpha-Androst-16-en-3 alpha-ol	HMDB
Androst-16-en-3 alpha-ol	HMDB
a-Androstenol	HMDB
Α-androstenol	HMDB
Androstenol	ChEBI

Chemical Formula

C₁₉H₃₀O

Average Molecular Weight

274.4409

Monoisotopic Molecular Weight

274.229665582

IUPAC Name

(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol

Traditional Name

(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol

CAS Registry Number

1153-51-1

SMILES

[H][C@@]12CC=C[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/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1

InChI Key

KRVXMNNRSSQZJP-PHFHYRSDSA-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
3-alpha-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-sterol (CHEBI:40933 )
C19 steroids (androgens) and derivatives (LMST02020008 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0005935)
Membrane (HMDB: HMDB0005935)

Source

Exogenous

Exogenous (HMDB: HMDB0005935)

Food

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: HMDB0005935)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142.75 °C	Not Available
Boiling Point	374.07 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3.64 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.030 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00036 g/L	ALOGPS
logP	5.13	ALOGPS
logP	4.07	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.23 m³·mol⁻¹	ChemAxon
Polarizability	33.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.45	31661259
DarkChem	[M-H]-	164.233	31661259
DeepCCS	[M-2H]-	199.44	30932474
DeepCCS	[M+Na]+	174.632	30932474
AllCCS	[M+H]+	171.7	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	174.7	32859911
AllCCS	[M+Na]+	175.5	32859911
AllCCS	[M-H]-	176.9	32859911
AllCCS	[M+Na-2H]-	177.0	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.17 minutes	32390414
Predicted by Siyang on May 30, 2022	18.4468 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.45 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2703.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	532.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	219.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	240.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	543.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	764.2 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	685.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1497.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	498.7 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	1579.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	321.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.5 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Androstenol	[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@]([H])(O)CC[C@]12C	2141.8	Standard polar	33892256
Androstenol	[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@]([H])(O)CC[C@]12C	2272.2	Standard non polar	33892256
Androstenol	[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@]([H])(O)CC[C@]12C	2303.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Androstenol,1TMS,isomer #1	C[C@@]12C=CC[C@H]1[C@@H]1CC[C@H]3C[C@H](O[Si](C)(C)C)CC[C@]3(C)[C@H]1CC2	2326.9	Semi standard non polar	33892256
Androstenol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]32)C1	2592.4	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 - Androstenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mk-1190000000-2998cb0396687c8b9897	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstenol GC-MS (1 TMS) - 70eV, Positive	splash10-0159-4249000000-8c4afa438fe5fff4e717	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 10V, Positive-QTOF	splash10-0a6r-0090000000-1be7cd81baa4d84a3789	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 20V, Positive-QTOF	splash10-0a6r-1390000000-ed025605b018708efcde	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 40V, Positive-QTOF	splash10-00mk-4590000000-855def90dad1c5c1e951	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 10V, Negative-QTOF	splash10-00di-0090000000-1541ebdd0dbc2495323f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 20V, Negative-QTOF	splash10-00di-0090000000-0ac5caa5bbe92d84a24d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 40V, Negative-QTOF	splash10-0a4l-1190000000-cff2612a42b766eff16e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 10V, Positive-QTOF	splash10-004i-0090000000-312b5e8b6401fa650e17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 20V, Positive-QTOF	splash10-00mk-1930000000-e0db6359d078ed97578f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 40V, Positive-QTOF	splash10-0002-6900000000-f1d874e55c03f8da2828	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 10V, Negative-QTOF	splash10-00di-0090000000-c0274c5a0ec76c02edd6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 20V, Negative-QTOF	splash10-00di-0090000000-c0274c5a0ec76c02edd6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenol 40V, Negative-QTOF	splash10-00di-0090000000-b42c05dd2b34d249baba	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01889

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112227

KNApSAcK ID

Not Available

Chemspider ID

92136

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Androstenol

METLIN ID

Not Available

PubChem Compound

101989

PDB ID

ATE

ChEBI ID

40933

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1010781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kwan TK, Trafford DJ, Makin HL, Mallet AI, Gower DB: GC-MS studies of 16-androstenes and other C19 steroids in human semen. J Steroid Biochem Mol Biol. 1992 Nov;43(6):549-56. [PubMed:1419890 ]
Gower DB, Holland KT, Mallet AI, Rennie PJ, Watkins WJ: Comparison of 16-androstene steroid concentrations in sterile apocrine sweat and axillary secretions: interconversions of 16-androstenes by the axillary microflora--a mechanism for axillary odour production in man? J Steroid Biochem Mol Biol. 1994 Mar;48(4):409-18. [PubMed:8142319 ]
Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA: The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors. J Pharmacol Exp Ther. 2006 May;317(2):694-703. Epub 2006 Jan 13. [PubMed:16415088 ]

Enzymes

Enzyme Details

1. Nuclear receptor subfamily 1 group I member 3

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element
Gene Name:: NR1I3
Uniprot ID:: Q14994
Molecular weight:: 39942.1

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for Androstenol (HMDB0005935)

MOL for HMDB0005935 (Androstenol)

3D MOL for HMDB0005935 (Androstenol)

3D SDF for HMDB0005935 (Androstenol)

3D-SDF for HMDB0005935 (Androstenol)

PDB for HMDB0005935 (Androstenol)

3D PDB for HMDB0005935 (Androstenol)

SMILES for HMDB0005935 (Androstenol)

INCHI for HMDB0005935 (Androstenol)

Structure for HMDB0005935 (Androstenol)

3D Structure for HMDB0005935 (Androstenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References