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Showing Compound Androstenedione (FDB021807)

Record Information
Version1.0
Creation date2011-04-11 17:01:39 UTC
Update date2019-11-26 03:20:53 UTC
Primary IDFDB021807
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAndrostenedione
DescriptionA delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins. [HMDB]
CAS Number63-05-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(4)-Androsten-3,17-dioneHMDB
[4-14C]-AndrostenedioneHMDB
[4-14C]Androst-4-ene-3,17-dioneHMDB
17-KetotestosteroneHMDB
3,17-Dioxoandrost-4-eneHMDB
4-Androsten-3,17-dioneHMDB
4-ANDROSTENE-3-17-dioneChEBI
4-Androstene-3,17-dioneChEBI
4-AndrostenedioneHMDB
Androst-4-ene-3,17-dioneChEBI
AndrostendioneHMDB
D4-Androstene-3,17-dioneHMDB
Delta(4)-Androsten-3,17-dioneChEBI
Delta(4)-Androstene-3,17-dioneChEBI
Delta4-AndrostenedioneHMDB
FecundinHMDB
δ(4)-androsten-3,17-dioneGenerator
δ(4)-androstene-3,17-dioneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.93ALOGPS
logP3.93ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.61 m³·mol⁻¹ChemAxon
Polarizability33.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O2
IUPAC name2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
InChI IdentifierInChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3
InChI KeyAEMFNILZOJDQLW-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC2=O
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
Classification
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
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAndrostenedione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0590000000-5a9584eeea2fe552809eSpectrum
Predicted GC-MSAndrostenedione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000j-5390000000-7be30effd5358ab0ade02021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-930e43a1a0a7194fa20c2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i00-1890000000-33f61600f4c6ce2679792021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7910000000-1cd51346e4131aa9d77f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-69c80a26e4f51bb27abb2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-69c80a26e4f51bb27abb2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-0a33ad63cf830bb094a92021-10-12View Spectrum
NMRNot Available
ChemSpider ID5898
ChEMBL IDCHEMBL274826
KEGG Compound IDC00280
Pubchem Compound ID6128
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01536
HMDB IDHMDB00053
CRC / DFC (Dictionary of Food Compounds) IDHLC84-H:HLC84-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2210012
KNApSAcK IDNot Available
HET IDASD
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
3-oxo-5-alpha-steroid 4-dehydrogenase 2SRD5A2P31213
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A1P18405
Testosterone 17-beta-dehydrogenase 3HSD17B3P37058
Androgen receptorARP10275
Polyprenol reductaseSRD5A3Q9H8P0
LeptinLEPP41159
Cytochrome P450, family 17, subfamily A, polypeptide 1CYP17A1Q1HB44
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference