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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 18:04:32 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0005935
Secondary Accession Numbers
  • HMDB0006571
  • HMDB05935
  • HMDB06571
Metabolite Identification
Common NameAndrostenol
DescriptionAndrostenol 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
Data?1582752369
Synonyms
ValueSource
(3alpha,5alpha)-Androst-16-en-3-olChEBI
3alpha-Hydroxyandrost-16-eneChEBI
Androst-16-en-3alpha-olChEBI
(3a,5a)-Androst-16-en-3-olGenerator
(3Α,5α)-androst-16-en-3-olGenerator
3a-Hydroxyandrost-16-eneGenerator
3Α-hydroxyandrost-16-eneGenerator
Androst-16-en-3a-olGenerator
Androst-16-en-3α-olGenerator
16,17-Androstene-3-olHMDB
3a-Hydroxy-5a-androst-16-eneHMDB
3a-HydroxyandrosteneHMDB
5a-Androst-16-en-3a-olHMDB
5alpha-Androst-16-en-3alpha-olHMDB
Androst-16-en-3-olHMDB
5 alpha-Androst-16-en-3 alpha-olHMDB
Androst-16-en-3 alpha-olHMDB
a-AndrostenolHMDB
Α-androstenolHMDB
AndrostenolChEBI
Chemical FormulaC19H30O
Average Molecular Weight274.4409
Monoisotopic Molecular Weight274.229665582
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 Number1153-51-1
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 KeyKRVXMNNRSSQZJP-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point142.75 °CNot Available
Boiling Point374.07 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3.64 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.030 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
logP5.13ALOGPS
logP4.07ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.23 m³·mol⁻¹ChemAxon
Polarizability33.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.4531661259
DarkChem[M-H]-164.23331661259
DeepCCS[M-2H]-199.4430932474
DeepCCS[M+Na]+174.63230932474
AllCCS[M+H]+171.732859911
AllCCS[M+H-H2O]+168.632859911
AllCCS[M+NH4]+174.732859911
AllCCS[M+Na]+175.532859911
AllCCS[M-H]-176.932859911
AllCCS[M+Na-2H]-177.032859911
AllCCS[M+HCOO]-177.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
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@]12C2141.8Standard polar33892256
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@]12C2272.2Standard non polar33892256
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@]12C2303.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Androstenol,1TMS,isomer #1C[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]1CC22326.9Semi standard non polar33892256
Androstenol,1TBDMS,isomer #1CC(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)C12592.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Androstenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mk-1190000000-2998cb0396687c8b98972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstenol GC-MS (1 TMS) - 70eV, Positivesplash10-0159-4249000000-8c4afa438fe5fff4e7172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 10V, Positive-QTOFsplash10-0a6r-0090000000-1be7cd81baa4d84a37892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 20V, Positive-QTOFsplash10-0a6r-1390000000-ed025605b018708efcde2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 40V, Positive-QTOFsplash10-00mk-4590000000-855def90dad1c5c1e9512017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 10V, Negative-QTOFsplash10-00di-0090000000-1541ebdd0dbc2495323f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 20V, Negative-QTOFsplash10-00di-0090000000-0ac5caa5bbe92d84a24d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 40V, Negative-QTOFsplash10-0a4l-1190000000-cff2612a42b766eff16e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 10V, Positive-QTOFsplash10-004i-0090000000-312b5e8b6401fa650e172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 20V, Positive-QTOFsplash10-00mk-1930000000-e0db6359d078ed97578f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 40V, Positive-QTOFsplash10-0002-6900000000-f1d874e55c03f8da28282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 10V, Negative-QTOFsplash10-00di-0090000000-c0274c5a0ec76c02edd62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 20V, Negative-QTOFsplash10-00di-0090000000-c0274c5a0ec76c02edd62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstenol 40V, Negative-QTOFsplash10-00di-0090000000-b42c05dd2b34d249baba2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01889
Phenol Explorer Compound IDNot Available
FooDB IDFDB112227
KNApSAcK IDNot Available
Chemspider ID92136
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostenol
METLIN IDNot Available
PubChem Compound101989
PDB IDATE
ChEBI ID40933
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1010781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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

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
  1. 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 ]