Human Metabolome Database Version 3.5

Showing metabocard for 5-Dehydroavenasterol (HMDB06852)

Record Information
Version 3.5
Creation Date 2008-08-13 07:49:58 -0600
Update Date 2013-02-08 17:15:26 -0700
HMDB ID HMDB06852
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Dehydroavenasterol
Description 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15783). It is the third to last step in the synthesis of Stigmasterol and is converted from delta 7-Avenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to Isofucosterol via the enzyme 7-dehydrocholesterol reductase [EC:1.3.1.21].
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C29H46O
Average Molecular Weight 410.6749
Monoisotopic Molecular Weight 410.354866094
IUPAC Name (2R,5S,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name (2R,5S,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
CAS Registry Number Not Available
SMILES C\C=C(/C(C)C)CC[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25?,26?,27?,28+,29-/m1/s1
InChI Key XPRWWANUPMYKMF-UUHDPGOWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Stigmastanes and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Isoprene
  • Secondary Alcohol
Direct Parent Stigmastanes and Derivatives
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.620E-04 g/L ALOGPS
LogP 8.24 ALOGPS
LogP 7.03 ChemAxon
LogS -6.20 ALOGPS
pKa (strongest acidic) 18.27 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 131.47 ChemAxon
Polarizability 51.98 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024118
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C15783 Link_out
BioCyc ID CPD-4126 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06852 Link_out
Metagene Link HMDB06852 Link_out
METLIN ID Not Available
PubChem Compound 23724575 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Lathosterol oxidase
Reactions:
Delta7-Avenasterol unknown 5-Dehydroavenasterol details
Gene Name: SC5DL
Uniprot ID: O75845 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 7-dehydrocholesterol reductase
Reactions:
5-Dehydroavenasterol unknown Avenasterol details
Gene Name: DHCR7
Uniprot ID: Q9UBM7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA