Human Metabolome Database Version 3.5

Showing metabocard for 5a-Cholest-8-en-3b-ol (HMDB06841)

Record Information
Version 3.5
Creation Date 2008-08-13 05:22:33 -0600
Update Date 2013-05-29 13:45:17 -0600
HMDB ID HMDB06841
Secondary Accession Numbers
  • HMDB06541
  • HMDB59618
Metabolite Identification
Common Name 5a-Cholest-8-en-3b-ol
Description 5a-Cholest-8-en-3b-ol is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in serum and bile of patients with cerebrotendinous xanthomatosis, compared to controls or in patients with cerebrotendinous xanthomatosis treated with chenodeoxycholic acid. Kidney transplant recipients had lower serum zymostenol when compared to controls. During consumption of plant stanol ester spread by hypercholesterolemic children, plant sterols in the plasma decrease and cholesterol precursor sterols such as zymostenol increase. (PMID: 15736111 Link_out, 16709621 Link_out, 16477216 Link_out, 12756385 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3beta,5alpha)Cholestenol
  2. 3beta-hydroxy-8(9)-cholestene
  3. 3beta-hydroxycholest-8(9)-ene
  4. 5-alpha-Cholest-8-en-3-beta-ol
  5. 5alpha-Cholest-8(9)-en-3beta-ol
  6. 5alpha-cholest-8-en-3beta-ol
  7. Cholest-8(9)-en-3beta-ol
  8. Cholesta-8(9)-en-3beta-ol
  9. delta(8)-Cholestenol
Chemical Formula C27H46O
Average Molecular Weight 386.6535
Monoisotopic Molecular Weight 386.354866094
IUPAC Name (2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional IUPAC Name 5α-cholest-8-en-3β-ol
CAS Registry Number 566-97-2
SMILES [H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3
InChI Identifier InChI=1S/C27H46O/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/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
InChI Key QETLKNDKQOXZRP-XTGBIJOFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols and Derivatives
Other Descriptors
  • 3beta-sterol(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(Lipidmaps)
Substituents
  • 3 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
  • Sesterterpene
Direct Parent Cholesterols and Derivatives
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
  • Endoplasmic reticulum
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 2.220E-04 g/L ALOGPS
LogP 6.59 ALOGPS
LogP 7.07 ChemAxon
LogS -6.24 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 5 ChemAxon
Refractivity 120.35 ChemAxon
Polarizability 50.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • 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 FDB024114
KNApSAcK ID Not Available
Chemspider ID 91952 Link_out
KEGG Compound ID C03845 Link_out
BioCyc ID CPD-8621 Link_out
BiGG ID 42633 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06841 Link_out
Metagene Link HMDB06841 Link_out
METLIN ID Not Available
PubChem Compound 101770 Link_out
PDB ID Not Available
ChEBI ID 16608 Link_out
References
Synthesis Reference Reindel, F.; Weickmann, A. Zymosterol. Ann. (1929), 475 86-100. CAN 24:5322 AN 1930:5322
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Clarenbach JJ, Lindenthal B, Dotti MT, Federico A, Kelleher JK, von Bergmann K: Isotopomer spectral analysis of intermediates of cholesterol synthesis in patients with cerebrotendinous xanthomatosis. Metabolism. 2005 Mar;54(3):335-44. Pubmed: 15736111 Link_out
  2. Oostendorp M, Engelke UF, Willemsen MA, Wevers RA: Diagnosing inborn errors of lipid metabolism with proton nuclear magnetic resonance spectroscopy. Clin Chem. 2006 Jul;52(7):1395-405. Epub 2006 May 18. Pubmed: 16709621 Link_out
  3. Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. Pubmed: 16477216 Link_out
  4. Ketomaki AM, Gylling H, Antikainen M, Siimes MA, Miettinen TA: Red cell and plasma plant sterols are related during consumption of plant stanol and sterol ester spreads in children with hypercholesterolemia. J Pediatr. 2003 May;142(5):524-31. Pubmed: 12756385 Link_out

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