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Showing metabocard for Androstenedione (LMDB00021)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:40:38 UTC
Update Date2016-07-19 23:06:50 UTC
LmdbLMDB00021
Secondary Accession NumbersNone
Metabolite Identification
Common NameAndrostenedione
DescriptionAndrostenedione is a 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Androstene-3,17-dioneChEBI
4-ANDROSTENE-3-17-dioneChEBI
delta(4)-Androsten-3,17-dioneChEBI
delta(4)-Androstene-3,17-dioneChEBI
Δ(4)-Androsten-3,17-dioneGenerator
Δ(4)-Androstene-3,17-dioneGenerator
(4)-Androsten-3,17-dioneHMDB
17-KetotestosteroneHMDB
3,17-Dioxoandrost-4-eneHMDB
4-Androsten-3,17-dioneHMDB
4-AndrostenedioneHMDB
Androst-4-ene-3,17-dioneHMDB, KEGG
AndrostendioneHMDB
D4-Androstene-3,17-dioneHMDB
delta4-AndrostenedioneHMDB
FecundinHMDB
delta 4 AndrostenedioneMeSH, HMDB
delta-4-AndrostenedioneMeSH, HMDB
4 Androstene 3,17 dioneMeSH, HMDB
AndrostenedioneHMDB
delta4-Androstene-3,17-dioneHMDB
Δ4-Androstene-3,17-dioneHMDB
Chemical FormulaC19H26O2
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
IUPAC Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
CAS Registry Number63-05-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=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/t14-,15-,16-,18-,19-/m0/s1
InChI KeyAEMFNILZOJDQLW-QAGGRKNESA-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
  • 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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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
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
Polarizability33.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-518e1ad38bcc73325b53Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-5172e05f9889ee2bfaf4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-8940000000-f2892fe3b281d44164c8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-007d-1960000000-167f1765b095da9d603bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-518e1ad38bcc73325b53Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-5172e05f9889ee2bfaf4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0590000000-502d6b821317a01a1990Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-36e848ba16b141eef47bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9600000000-712954fc35a84c8217deSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-f8e9aa16b4b208b69f7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-8940000000-e12025ea2b7808c64b9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-6910000000-b616785c86a92f46158eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-9800000000-73e545a1eb2232d55371Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-735473bc44dd70e29259Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-114675a4457063901f2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-0347db9e9578e8d5d6f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05pc-0490000000-d4049441f1c172450dc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-4790000000-355bc0834a6465ecad30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-887b6f223b77c683ef99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-9dafdd780cca012f1fb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-2190000000-264074b1eefeed0e3103Spectrum
MSMass Spectrum (Electron Ionization)splash10-059m-3940000000-9cb32ac21e46afb2829aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified0.000716 uMNot AvailableBovine details
SerumDetected and Quantified<0.000545 uMNot AvailableBovine details
SerumDetected and Quantified<0.000545 uMNot AvailableBovine details
SerumDetected and Quantified0.000320&0.000545 uMNot AvailableBovine details
DrugBank IDDB01536
HMDB IDHMDB0000053
FooDB IDFDB030678
Phenol Explorer IDNot Available
KNApSAcK IDC00003644
BiGG ID2210012
BioCyc IDANDROST4ENE
METLIN ID2795
PDB IDNot Available
Wikipedia LinkAndrostenedione
Chemspider ID5898
ChEBI ID16422
PubChem Compound ID6128
Kegg Compound IDC00280
YMDB IDNot Available
ECMDB IDM2MDB005064
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available