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Record Information
Version3.6
Creation Date2007-04-12 18:04:32 UTC
Update Date2016-02-11 01:07:19 UTC
HMDB IDHMDB05935
Secondary Accession Numbers
  • 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
Thumb
Synonyms
ValueSource
(3a,5a)-Androst-16-en-3-olHMDB
(3alpha,5alpha)-Androst-16-en-3-olHMDB
16,17-Androstene-3-olHMDB
3a-Hydroxy-5a-androst-16-eneHMDB
3a-Hydroxyandrost-16-eneHMDB
3a-HydroxyandrosteneHMDB
3alpha-Hydroxyandrost-16-eneHMDB
5a-Androst-16-en-3a-olHMDB
5alpha-Androst-16-en-3alpha-olHMDB
Androst-16-en-3-olHMDB
Androst-16-en-3alpha-olHMDB
Chemical FormulaC19H30O
Average Molecular Weight274.4409
Monoisotopic Molecular Weight274.229665582
IUPAC Name(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-ol
Traditional Nameandrostenol
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 KeyInChIKey=KRVXMNNRSSQZJP-PHFHYRSDSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142.75 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000355 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.23 m3·mol-1ChemAxon
Polarizability33.67 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01889
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012828
KNApSAcK IDNot Available
Chemspider ID92136
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostenol
NuGOwiki LinkHMDB05935
Metagene LinkHMDB05935
METLIN IDNot Available
PubChem Compound101989
PDB IDATE
ChEBI ID40933
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. [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. [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. [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. [10592235 ]