Human Metabolome Database Version 3.5

Showing metabocard for 5-Dehydroepisterol (HMDB06848)

Record Information
Version 3.5
Creation Date 2008-08-13 07:36:27 -0600
Update Date 2013-02-08 17:15:26 -0700
HMDB ID HMDB06848
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Dehydroepisterol
Description 5-Dehydroepisterol is an intermediate in the biosynthesis of steroids (KEGG ID C15780), and is converted from Episterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to 24-Methylenecholesterol 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
  1. Campesta-7,24(28)-dien-3beta-ol
  2. Ergosta-5,7,24(28)-trien-3beta-ol
Chemical Formula C28H44O
Average Molecular Weight 396.6484
Monoisotopic Molecular Weight 396.33921603
IUPAC Name (1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name 5-dehydroepisterol
CAS Registry Number 23582-83-4
SMILES [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C
InChI Identifier InChI=1S/C28H44O/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/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1
InChI Key ZEPNVCGPJXYABB-LOIOQLKMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Ergosterols and Derivatives
Other Descriptors
  • 3beta-sterol(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Ergosterols and C24-methyl derivatives(KEGG)
  • Ergosterols and C24-methyl derivatives(Lipidmaps)
  • Triterpenes
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Isoprene
  • Secondary Alcohol
Direct Parent Ergosterols 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 6.030E-04 g/L ALOGPS
LogP 7.64 ALOGPS
LogP 6.65 ChemAxon
LogS -5.82 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 125.79 ChemAxon
Polarizability 50.73 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 FDB024117
KNApSAcK ID Not Available
Chemspider ID 9069833 Link_out
KEGG Compound ID C15780 Link_out
BioCyc ID CPD-700 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06848 Link_out
Metagene Link HMDB06848 Link_out
METLIN ID Not Available
PubChem Compound 10894570 Link_out
PDB ID Not Available
ChEBI ID 52972 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Lathosterol oxidase
Reactions:
Episterol unknown 5-Dehydroepisterol details
Gene Name: SC5DL
Uniprot ID: O75845 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 7-dehydrocholesterol reductase
Reactions:
5-Dehydroepisterol unknown 24-Methylenecholesterol details
Gene Name: DHCR7
Uniprot ID: Q9UBM7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA