Human Metabolome Database Version 3.5

Showing metabocard for Zymosterol intermediate 2 (HMDB06271)

Record Information
Version 3.5
Creation Date 2007-05-22 14:50:56 -0600
Update Date 2013-05-29 13:43:22 -0600
HMDB ID HMDB06271
Secondary Accession Numbers None
Metabolite Identification
Common Name Zymosterol intermediate 2
Description Zymosterol is the precursor of cholesterol and is found in the plasma membrane. zymosterol circulates within the cells. The structural features of zymosterol provided optimal substrate acceptability. In human fibroblasts, zymosterol is converted to cholesterol solely in the rough ER. Little or no zymosterol or cholesterol accumulates in the rough ER in vivo. Newly synthesized zymosterol moves to the plasma membrane without a detectable lag and with a half-time of 9 min, about twice as fast as cholesterol. The pool of radiolabeled zymosterol in the plasma membrane turns over rapidly, faster than does intracellular cholesterol. Thus, plasma membrane zymosterol is not stagnant. [3H]Zymosterol pulsed into intact cells is initially found in the plasma membrane. (PMID: 1939176 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3b,5a)- Cholesta-8,24-dien-3-ol
  2. 5alpha-Cholesta-8,24-dien-3beta-ol
  3. Cholest-8,24-dien-3b-ol
  4. Cholesta-8,24-dien-3-ol
  5. Delta8,24-Cholestadien-3beta-ol
  6. Zymosterol
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-1(10)-en-5-ol
Traditional IUPAC Name zymosterol
CAS Registry Number 128-33-6
SMILES [H][C@@](C)(CCC=C(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/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/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
InChI Key CGSJXLIKVBJVRY-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(KEGG)
  • Cholesterol and derivatives(Lipidmaps)
Substituents
  • 3 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • 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 110 °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 9.980E-04 g/L ALOGPS
LogP 6.51 ALOGPS
LogP 6.66 ChemAxon
LogS -5.59 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 121.2 ChemAxon
Polarizability 49.86 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 FDB023869
KNApSAcK ID Not Available
Chemspider ID 83724 Link_out
KEGG Compound ID C05437 Link_out
BioCyc ID Not Available
BiGG ID 1454806 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06271 Link_out
Metagene Link HMDB06271 Link_out
METLIN ID Not Available
PubChem Compound 92746 Link_out
PDB ID Not Available
ChEBI ID 18252 Link_out
References
Synthesis Reference Dolle, Roland E.; Schmidt, Stanley J.; Kruse, Lawrence I. Synthesis of zymosterol: salient intermediate of fungal and mammalian sterol biosynthesis. Journal of the Chemical Society, Chemical Communications (1988), (1), 19-21.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Lange Y, Echevarria F, Steck TL: Movement of zymosterol, a precursor of cholesterol, among three membranes in human fibroblasts. J Biol Chem. 1991 Nov 15;266(32):21439-43. Pubmed: 1939176 Link_out

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:
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