androsta-1,4-diene-3,17-dione (PAMDB120259)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120259
Identification
Name: androsta-1,4-diene-3,17-dione
Description:A steroid that consists of androstane having double bonds at positions 1 and 4 and two keto groups at positions 3 and 17.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1,4-Androstadiene-3,17-dione
  • 1-Dehydroandrostenedione
  • ADD
  • ADT
  • androsta-1,4-diene-3,17-dione
  • ANDROSTA-1,4-DIENE-3,17-DIONE
  • Androstadienedione
  • Boldione
Chemical Formula: C19H24O2
Average Molecular Weight: 284.397
Monoisotopic Molecular Weight: 284.17764
InChI Key: LUJVUUWNAPIQQI-QAGGRKNESA-N
InChI:InChI=1S/C19H24O2/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/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
CAS number: 897-06-3
IUPAC Name:androsta-1,4-diene-3,17-dione
Traditional IUPAC Name: androsta-1,4-diene-3,17-dione
SMILES:CC34(C=CC(=O)C=C(CC[CH]1([CH](CCC2(C)(C(CC[CH]12)=O))3))4)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct Parent Androgens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 mg/mLALOGPS
logP2.78ALOGPS
logP3.93ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.83ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.7 m3·mol-1ChemAxon
Polarizability32.47 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
androst-4-ene-3,17-dione + Acceptor → androsta-1,4-diene-3,17-dione + Donor-H2
androsta-1,4-diene-3,17-dione + Oxygen + NADH + Hydrogen ion → 9α-hydroxyandrosta-1,4-diene-3,17-dione + NAD+ + Water
Pathways:
Spectra
Spectra: Not Available
References
References:
  • Weber S, Puripattanavong J, Brecht V, Frahm AW (2000)Phytochemical investigation of Aglaia rubiginosa. Journal of natural products 63, Pubmed: 10843575
Synthesis Reference: Brzezowska, Ewa; Kowalski, Tadeusz. Method for obtaining androsta-1,4-diene-3,17-dione. Pol. (2007), 4pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
HMDBHMDB03422
CHEBI40799