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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-22 20:50:56 UTC
Update Date2022-09-22 18:34:19 UTC
HMDB IDHMDB0006271
Secondary Accession Numbers
  • HMDB06271
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
Data?1582752378
Synonyms
ValueSource
5alpha-Cholesta-8,24-dien-3beta-olChEBI
delta8,24-Cholestadien-3beta-olChEBI
ZymostrolChEBI
5a-Cholesta-8,24-dien-3b-olGenerator
5Α-cholesta-8,24-dien-3β-olGenerator
delta8,24-Cholestadien-3b-olGenerator
Δ8,24-cholestadien-3β-olGenerator
Zymosterol intermediic acid 2Generator
Δ8,24-cholestadien-3b-olHMDB
(3b,5a)- Cholesta-8,24-dien-3-olHMDB
Cholest-8,24-dien-3b-olHMDB
Cholesta-8,24-dien-3-olHMDB
ZymosterolHMDB
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 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
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
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point110 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.001 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 Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.2 m³·mol⁻¹ChemAxon
Polarizability49.72 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.10431661259
DarkChem[M-H]-186.89831661259
DeepCCS[M-2H]-230.91630932474
DeepCCS[M+Na]+205.42130932474
AllCCS[M+H]+204.432859911
AllCCS[M+H-H2O]+202.232859911
AllCCS[M+NH4]+206.532859911
AllCCS[M+Na]+207.132859911
AllCCS[M-H]-204.832859911
AllCCS[M+Na-2H]-206.332859911
AllCCS[M+HCOO]-208.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Zymosterol intermediate 2[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])CC32447.7Standard polar33892256
Zymosterol intermediate 2[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])CC33116.5Standard non polar33892256
Zymosterol intermediate 2[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])CC33150.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Zymosterol intermediate 2,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C[C@@H]1CC33184.9Semi standard non polar33892256
Zymosterol intermediate 2,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1CC33414.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zymosterol intermediate 2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cfr-1019000000-1b05483747ddc32500b02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zymosterol intermediate 2 GC-MS (1 TMS) - 70eV, Positivesplash10-002f-3106900000-eda3cfead337ce02b2b52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zymosterol intermediate 2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zymosterol intermediate 2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 10V, Positive-QTOFsplash10-014r-0019000000-010b245dedfb160716ba2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 20V, Positive-QTOFsplash10-014i-2149000000-c0828080ef844c1d5c692016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 40V, Positive-QTOFsplash10-02vi-3259000000-96993d821222323ab0752016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 10V, Negative-QTOFsplash10-001i-0009000000-0373115d11504acc8b812016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 20V, Negative-QTOFsplash10-001i-0009000000-cc742e0af833cc290a8f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 40V, Negative-QTOFsplash10-0gb9-1019000000-87e4aab6501a99f5baec2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 10V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 20V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 40V, Negative-QTOFsplash10-001i-0019000000-384e7aa03192295e15892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 10V, Positive-QTOFsplash10-000i-0019000000-3fe44ab0178bb12e2a162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 20V, Positive-QTOFsplash10-001i-4249000000-ee1fd80800f89af74a912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zymosterol intermediate 2 40V, Positive-QTOFsplash10-0abc-8930000000-32bc5a989db5c704eabf2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-21Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031258
KNApSAcK IDC00023749
Chemspider ID83724
KEGG Compound IDC05437
BioCyc IDNot Available
BiGG ID1454806
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92746
PDB IDNot Available
ChEBI ID18252
Food Biomarker OntologyNot Available
VMH IDZYMST
MarkerDB IDNot Available
Good Scents IDNot Available
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 → 5alpha-Cholesta-7,24-dien-3beta-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 → 5alpha-Cholest-8-en-3beta-ol + NADPdetails