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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
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 NameNot Available
Traditional NameNot Available
CAS Registry Number846-46-8
SMILESNot Available
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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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