Showing metabocard for Androstanedione (BMDB0000899)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:18 UTC
Update Date2020-05-11 20:55:15 UTC
BMDB IDBMDB0000899
Secondary Accession Numbers
  • BMDB00899
Metabolite Identification
Common NameAndrostanedione
DescriptionAndrostanedione 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. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Androstanedione exists in all living organisms, ranging from bacteria to humans. Androstanedione participates in a number of enzymatic reactions, within cattle. In particular, Androstanedione can be biosynthesized from androstenedione; which is mediated by the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase 1. In addition, Androstanedione can be converted into androsterone; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, androstanedione is involved in the metabolic pathway called the androstenedione metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5alpha-Androstan-3,17-dioneChEBI
5a-Androstan-3,17-dioneGenerator
5Α-androstan-3,17-dioneGenerator
(5a)-Androstane-3,17-dioneHMDB
5-alpha-Androstane-3,17-dioneHMDB
5a-Androsta-3,17-dioneHMDB
5a-Androstane-3, 17-dioneHMDB
5a-Androstane-3,17-dioneHMDB
5a-AndrostanedioneHMDB
5alpha-Androstane-3,17-dioneHMDB
Androstane-3,17-dioneHMDB
Androstane-3,7-dioneHMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomerHMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomerHMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomerHMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomerHMDB
Androstane-3,17-dione, (5beta)-isomerHMDB
3,17-Dioxy-5 alpha-androstaneHMDB
5 alpha-AndrostanedioneHMDB
5 beta-Androstane-3,17-dioneHMDB
5 alpha-Androstane-3,17-dioneHMDB
Androstane-3,17-dione, (5alpha)-isomerHMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
Traditional Name(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
CAS Registry Number846-46-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
InChI KeyRAJWOBJTTGJROA-WZNAKSSCSA-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-oxo-5-alpha-steroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 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 but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133.5 - 134.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.4ALOGPS
logP3.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.78 m³·mol⁻¹ChemAxon
Polarizability33.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003u-9711000000-845e34a01c44999f2dedView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-2790000000-3265da77fd4cc7bfa1c9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003u-9711000000-845e34a01c44999f2dedView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0490000000-e4819053bc47c4809a6cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-decf354145d0bc46e624View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01vk-4910000000-1f05b00fe5f61dd134c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05ng-9800000000-ef0555e1d54150aaffd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0aou-0290000000-ffd1b454b311f471cb73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0390000000-f4995b2047bec58846f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0390000000-a4cf943964aae2cffee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-8b26abdeab6d06d616e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-0490000000-5411cf1f548c371b71f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mkg-2690000000-fd3043c5fcf860949b79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-be391ca3b57229eb2b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-0c9ee67f63fb1f48c00aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3190000000-4d4ec5ab2ebbcfdebbd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a3a5ee5e1cdb4d550aacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-0970000000-66d8653b98d2df4aa327View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-2a46c86775b66edae018View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-0497207bd4a67a50d8d8View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Semen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000899
DrugBank IDDB01561
Phenol Explorer Compound IDNot Available
FooDB IDFDB022307
KNApSAcK IDNot Available
Chemspider ID193520
KEGG Compound IDC00674
BioCyc IDCPD-342
BiGG ID42505
Wikipedia LinkAndrostanedione
METLIN ID5855
PubChem Compound222865
PDB IDNot Available
ChEBI ID15994
References
Synthesis ReferenceMarker, Russell E.; Kamm, Oliver; Jones, David M.; Oakwood, Thomas S. Sterols. VIII. Preparation of androstanedione from allopregnanediol. Journal of the American Chemical Society (1937), 59 614-16.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available