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Record Information
Version3.6
Creation Date2009-04-06 16:20:50 UTC
Update Date2013-05-13 23:09:18 UTC
HMDB IDHMDB12196
Secondary Accession NumbersNone
Metabolite Identification
Common NameCampest-4-en-3-one
DescriptionCampest-4-en-3-one is an intermediate in Brassinolide Biosynthesis pathway.The conversion of the membrane Sterol Campesterol to BL occurs via a series of reductions, hydroxylations, epimerizations and oxidations that have been extensively studied in several species. The conversion of Campesterol to Campestanol is not a single step, but composed of the biosynthetic sequence of Campesterol 4-en-3Beta-ol ---> 4-en-3-one ---> 3-one ---> Campestanol in Arabidopsis. In the first step, Campesterol is converted to Campest-4-en-3Beta-ol in presence of enzyme Delta-5-3-Ketosteroid Isomerase. Enzymes that catalyze the conversion from 3-Beta-Hydroxy-Delta,5-6-Steroid to 3-oxo-Delta-4-5 Isomerase have been reported in Bacteria and Mammals. Campest-4-en-3 Beta-ol is converted to Campest-4-en-3-one in presence of enzyme 3-Beta-Hydroxysteroid Dehydrogenase. In the next step, Campest-4-en-3-one is converted to Campestanol via 5-Alpha-Campestan-3-one. 3-Oxo-5Alpha-Steroid 4-Dehydrogenase family members (encoded by Det2 in Arabidopsis) catalyze the formation of 5-Alpha-Campestan-3-one.
Structure
Thumb
Synonyms
  1. (24R)-ergost-4-en-3-one
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(2R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(2R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry NumberNot Available
SMILES
CC(C)[C@H](C)CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-20,23-26H,7-16H2,1-6H3/t19-,20-,23?,24?,25?,26?,27+,28-/m1/s1
InChI KeyQQIOPZFVTIHASB-PHOXBLGLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassErgosterols and Derivatives
Other Descriptors
  • 3-oxo steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Ergosterols and C24-methyl derivatives(KEGG)
  • Ergosterols and C24-methyl derivatives(Lipidmaps)
  • Triterpenes
Substituents
  • 3 Keto Steroid
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
Direct ParentErgosterols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.92e-05ALOGPS
logP6.4ALOGPS
logP7.97ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.11 m3·mol-1ChemAxon
Polarizability51.19 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB018055
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-3945
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12196
Metagene LinkHMDB12196
METLIN IDNot Available
PubChem Compound25200612
PDB IDNot Available
ChEBI ID18534
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265