Human Metabolome Database Version 3.5

Showing metabocard for 5a-Cholesta-7,24-dien-3b-ol (HMDB06842)

Record Information
Version 3.5
Creation Date 2008-08-13 05:32:19 -0600
Update Date 2013-02-08 17:15:25 -0700
HMDB ID HMDB06842
Secondary Accession Numbers
  • HMDB00997
Metabolite Identification
Common Name 5a-Cholesta-7,24-dien-3b-ol
Description 5alpha-Cholesta-7,24-dien-3beta-ol is involved in the biosynthesis of steroids. 5alpha-Cholesta-7,24-dien-3beta-ol is reversibly converted to 5alpha-Cholest-7-en-3beta-ol by delta24-sterol reductase [EC:1.3.1.72]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to zymosterol by cholestenol delta-isomerase [EC:5.3.3.5]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to 7-Dehydrodesmosterol. 5a-Cholesta-7,24-dien-3b-ol is a substrate for 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5 alpha-Cholesta-7,24-dien-3beta-ol
  2. 5alpha-Cholesta-7,24-dien-3beta-ol
Chemical Formula C27H44O
Average Molecular Weight 384.6377
Monoisotopic Molecular Weight 384.33921603
IUPAC Name (2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional IUPAC Name (2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number 651-54-7
SMILES [H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25?,26+,27-/m1/s1
InChI Key PKEPPDGGTSZLBL-FZAJRYLSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Sesterterpenes
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(KEGG)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • Secondary Alcohol
  • Steroid
Direct Parent Sesterterpenes
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 147 - 151 °C 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 1.640E-04 g/L ALOGPS
LogP 7.40 ALOGPS
LogP 6.71 ChemAxon
LogS -6.37 ALOGPS
pKa (strongest acidic) 18.36 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 121.47 ChemAxon
Polarizability 49.73 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Steroid Biosynthesis SMP00023 map00100 Link_out
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 FDB024115
KNApSAcK ID Not Available
Chemspider ID 389550 Link_out
KEGG Compound ID C05439 Link_out
BioCyc ID 5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL Link_out
BiGG ID 45811 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06842 Link_out
Metagene Link HMDB06842 Link_out
METLIN ID 5928 Link_out
PubChem Compound 440670 Link_out
PDB ID Not Available
ChEBI ID 16290 Link_out
References
Synthesis Reference Moreau, Jacques P.; Aberhart, Donald J.; Caspi, Eliahu. Synthesis of 5a-cholesta-7,24-dien-3b-ol and cholesta-5,7,24-trien-3b-ol. Journal of Organic Chemistry (1974), 39(14), 2018-23.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
Reactions:
Zymosterol intermediate 2 unknown 5a-Cholesta-7,24-dien-3b-ol details
Gene Name: EBP
Uniprot ID: Q15125 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta(24)-sterol reductase
Reactions:
Lathosterol + NADP unknown 5a-Cholesta-7,24-dien-3b-ol + NADPH + Hydrogen Ion details
Gene Name: DHCR24
Uniprot ID: Q15392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA