Showing Compound Card for Androstadienoned (CDB005842)

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Record Information
Version1.0
Created at2020-04-27 17:02:01 UTC
Updated at2021-01-04 18:49:24 UTC
CannabisDB IDCDB005842
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAndrostadienoned
DescriptionAndrosta-4,16-dien-3-one also known as Androstadienone belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. Steroids consisting of a core structure of four rings arranged in a specific molecular configuration. Steroids are different by their functional groups attached to this four-ring core and by the oxidation state of the rings. Steroids are biologically active compounds found in plants, animals and fungi. Androstadienone is an endogenous steroid that has been described as having potent pheromone-like activities in humans (PMID: 17287500 ). In particular, Androstadienone, in picogram quantities, has been shown to have "significant reduction of nervousness, tension and other negative feeling states" in females (PMID: 10737699 ). Androstadienone is structurally related to the androgen sex hormones; however it does not exhibit any androgenic or anabolic effects. It is synthesized from androstadienol by 3β-hydroxysteroid dehydrogenase and can be converted into androstenone (a more potent and odorous pheromone) by 5α-reductase, which can subsequently be converted into 3α-androstenol or 3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase. Androstadienone is also a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,16-Androstadien-3-oneMeSH
Androsta-4,16-dien-3-oneMeSH
Chemical FormulaC19H26O
Average Molecular Weight270.42
Monoisotopic Molecular Weight270.1984
IUPAC Name(1S,2R,10S,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one
Traditional Name(1S,2R,10S,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one
CAS Registry Number4075-07-4
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC=C2
InChI Identifier
InChI=1S/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3/t15-,16-,17-,18-,19-/m0/s1
InChI KeyHNDHDMOSWUAEAW-VMXHOPILSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.13ALOGPS
logP4.23ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)19.08ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.03 m³·mol⁻¹ChemAxon
Polarizability32.35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAndrostadienoned, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-0090000000-fc7a466f267b10e350bd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-2290000000-7ec8261a11f598b485ac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00dj-5890000000-c23e88a12b4a246d124e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0592-5940000000-f7f4e4434dff08bb181a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-052b-6920000000-fa3dca4d2f612bda00812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-052b-6910000000-5d45315689bb350166aa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4j-7900000000-2d3a0c437d59c86bcd0b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-0a4j-9700000000-b6c70788d10980517f212020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-0a6v-9500000000-16dcf069d1395e083cfb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-056v-9300000000-006d6237a5076c48e65b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-004l-9300000000-1f28efbad4c68c1e2df12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-00ou-9300000000-d83556c1505d4bc476ab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0udj-2950000000-c9ab4e61bc1f870d986a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-004i-9000000000-3fc57d92cb9e245947b02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00lr-9000000000-37aa8de72aa999b579d72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-06r2-0920000000-de8e914fa352317ac7522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0aor-0900000000-9905ebe27110b82d270b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0udi-0290000000-c7f95f769e64cf9fac872020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0udi-0590000000-b3f11784037d2ffdabe82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0udi-1980000000-5ed530d4091004e02d452020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0zfs-1930000000-68227f5d21aade50e30b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-0537-2910000000-8c1c023437e202b0c44c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-05ox-2900000000-b1ac78f60a446889888f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 29V, positivesplash10-05r3-2900000000-f8b6bc5bd1f67b29cafe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 35V, positivesplash10-0fvl-2900000000-386afa19fc5c5a899d112020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID83932
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostadienone
METLIN IDNot Available
PubChem Compound92979
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Wyart C, Webster WW, Chen JH, Wilson SR, McClary A, Khan RM, Sobel N: Smelling a single component of male sweat alters levels of cortisol in women. J Neurosci. 2007 Feb 7;27(6):1261-5. doi: 10.1523/JNEUROSCI.4430-06.2007. [PubMed:17287500 ]
  2. Grosser BI, Monti-Bloch L, Jennings-White C, Berliner DL: Behavioral and electrophysiological effects of androstadienone, a human pheromone. Psychoneuroendocrinology. 2000 Apr;25(3):289-99. doi: 10.1016/s0306-4530(99)00056-6. [PubMed:10737699 ]