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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:39:23 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006849
Secondary Accession Numbers
  • HMDB06849
Metabolite Identification
Common Name24-Methylenecholesterol
Description24-Methylenecholesterol, also known as chalinasterol or ostreasterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 24-methylenecholesterol is considered to be a sterol lipid molecule. 24-Methylenecholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-dehydroepisterol by 7-dehydrocholesterol reductase (EC 1.3.1.21). 24-Methylenecholesterol is converted into campesterol by delta24-sterol reductase (EC 1.3.1.72).
Structure
Data?1588352617
Synonyms
ValueSource
24-MethylencholesterolChEBI
24-Methylene-cholest-5-en-3beta-olChEBI
ChalinasterolChEBI
OstreasterolChEBI
24-Methylene-cholest-5-en-3b-olGenerator
24-Methylene-cholest-5-en-3β-olGenerator
Ergosta-5,24(28)-dien-3 beta-olMeSH
(3beta)-Ergosta-5,24(28)-dien-3-olHMDB
(3β)-Ergosta-5,24(28)-dien-3-olHMDB
24-Methylcholesta-5,24(28)-dien-3beta-olHMDB
24-Methylcholesta-5,24(28)-dien-3β-olHMDB
24-Methylenecholest-5-en-3beta-olHMDB
24-Methylenecholest-5-en-3β-olHMDB
24-MethylenecholesterolHMDB
Ergosta-5,24(28)-dien-3beta-olHMDB
Ergosta-5,24(28)-dien-3β-olHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.675
Monoisotopic Molecular Weight398.354866101
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number474-63-5
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C
InChI Identifier
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18,20,22-26,29H,3,7-8,10-17H2,1-2,4-6H3/t20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
InChI KeyINDVLXYUCBVVKW-PXBBAZSNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP6.61ALOGPS
logP7.05ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.94 m³·mol⁻¹ChemAxon
Polarizability51.51 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
DeepCCS[M-2H]-234.91230932474
DeepCCS[M+Na]+209.17530932474
AllCCS[M+H]+206.232859911
AllCCS[M+H-H2O]+204.232859911
AllCCS[M+NH4]+208.132859911
AllCCS[M+Na]+208.732859911
AllCCS[M-H]-205.332859911
AllCCS[M+Na-2H]-207.132859911
AllCCS[M+HCOO]-209.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
24-Methylenecholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C2538.4Standard polar33892256
24-Methylenecholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C3200.8Standard non polar33892256
24-Methylenecholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C3262.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
24-Methylenecholesterol,1TMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3263.2Semi standard non polar33892256
24-Methylenecholesterol,1TBDMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3494.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 24-Methylenecholesterol 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 - 24-Methylenecholesterol 10V, Positive-QTOFsplash10-0002-0029000000-71f1483e076b063b7b602021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenecholesterol 20V, Positive-QTOFsplash10-0a59-9186000000-7cc2bc6023dd1fe0b7512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenecholesterol 40V, Positive-QTOFsplash10-0536-9510000000-57fc3dd27bd0033df4232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenecholesterol 10V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenecholesterol 20V, Negative-QTOFsplash10-0002-0009000000-98dfe229433f1d54d64c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Methylenecholesterol 40V, Negative-QTOFsplash10-0002-0009000000-1e6bd3683f62bedab8952021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001361
KNApSAcK IDC00007271
Chemspider ID83160
KEGG Compound IDC15781
BioCyc IDCPD-706
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92113
PDB IDNot Available
ChEBI ID19812
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Reactions
5-Dehydroepisterol → 24-Methylenecholesteroldetails
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
24-Methylenecholesterol + NADPH + Hydrogen Ion → Campesterol + NADPdetails