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Record Information
Version3.6
Creation Date2007-05-22 20:50:56 UTC
Update Date2013-05-29 19:43:22 UTC
HMDB IDHMDB06271
Secondary Accession NumbersNone
Metabolite Identification
Common NameZymosterol intermediate 2
DescriptionZymosterol 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 ).
Structure
Thumb
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 FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
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 Namezymosterol
CAS Registry Number128-33-6
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 KeyCGSJXLIKVBJVRY-XTGBIJOFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassCholesterols 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 ParentCholesterols and Derivatives
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point110 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility9.980E-04 g/LALOGPS
logP6.51ALOGPS
logP6.66ChemAxon
logS-5.6ALOGPS
pKa (strongest acidic)18.36ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count4ChemAxon
refractivity121.2ChemAxon
polarizability49.86ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023map00100
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023869
KNApSAcK IDNot Available
Chemspider ID83724
KEGG Compound IDC05437
BioCyc IDNot Available
BiGG ID1454806
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06271
Metagene LinkHMDB06271
METLIN IDNot Available
PubChem Compound92746
PDB IDNot Available
ChEBI ID18252
References
Synthesis ReferenceDolle, 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

Enzymes

General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Reactions
Zymosterol intermediate 2 → 5a-Cholesta-7,24-dien-3b-oldetails
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Zymosterol intermediate 2 + NADPH + Hydrogen Ion → 5a-Cholest-8-en-3b-ol + NADPdetails