9α-hydroxyandrosta-1,4-diene-3,17-dione (PAMDB120268)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120268
Identification
Name: 9α-hydroxyandrosta-1,4-diene-3,17-dione
Description:A steroid that consists of androstane having double bonds at positions 1 and 4, two keto groups at positions 3 and 17 and a hydroxy group at position 9.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 9alpha-Hydroxyandrosta-1,4-diene-3,17-dione
  • 9α-hydroxyandrosta-1,4-diene-3,17-dione
Chemical Formula: C19H24O3
Average Molecular Weight: 300.397
Monoisotopic Molecular Weight: 300.17255
InChI Key: JCEUDJXAQHPZGL-PLOWYNNNSA-N
InChI:InChI=1S/C19H24O3/c1-17-9-10-19(22)15(14(17)5-6-16(17)21)4-3-12-11-13(20)7-8-18(12,19)2/h7-8,11,14-15,22H,3-6,9-10H2,1-2H3/t14-,15-,17-,18-,19+/m0/s1
CAS number: Not Available
IUPAC Name:9-hydroxyandrosta-1,4-diene-3,17-dione
Traditional IUPAC Name: Not Available
SMILES:CC13(C(=O)CC[CH]1[CH]2(CCC4(C(C)(C2(O)CC3)C=CC(=O)C=4)))
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Steroids and steroid derivatives
Sub ClassAndrostane steroids
Direct Parent Androgens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 17-oxosteroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
  • a 3-oxo-\u0026Delta;\u003cSUP\u003e4\u003c/SUP\u003e-steroid (CPD-13680)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass300.3910ChemAxon
logP2.9783ChemAxon
H-bond acceptors3ChemAxon
H-bond donors1ChemAxon
Rotatable bonds0ChemAxon
PSA54.3700ChemAxon
RO5 violations0ChemAxon
RO3 violations1ChemAxon
Refractivity85.1228ChemAxon
Atoms46ChemAxon
Rings4ChemAxon
Heavy atoms22ChemAxon
Hydrogen atoms24ChemAxon
Heteroatoms3ChemAxon
N/O atoms3ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers5ChemAxon
R/S chiral centers0ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers5ChemAxon
Stereo double bonds0ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds0ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
9α-hydroxyandrosta-1,4-diene-3,17-dione → 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione
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:
  • Petrusma M, Dijkhuizen L, van der Geize R (2009)Rhodococcus rhodochrous DSM 43269 3-ketosteroid 9alpha-hydroxylase, a two-component iron-sulfur-containing monooxygenase with subtle steroid substrate specificity. Applied and environmental microbiology 75, Pubmed: 19561185
  • Capyk JK, D'Angelo I, Strynadka NC, Eltis LD (2009)Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis. The Journal of biological chemistry 284, Pubmed: 19234303
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI63641