Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:13:21 UTC
Update Date2022-03-07 03:17:54 UTC
HMDB IDHMDB0062391
Secondary Accession Numbers
  • HMDB62391
Metabolite Identification
Common Name4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol
Description4alpha-hydroxymethyl-4beta-methyl-5alpha-8-cholesten-3beta-ol, also known as 4α-(hydroxymethyl)-4-methyl-5α-cholest-8-en-3β-ol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 4alpha-hydroxymethyl-4beta-methyl-5alpha-8-cholesten-3beta-ol is considered to be a sterol lipid molecule. 4alpha-hydroxymethyl-4beta-methyl-5alpha-8-cholesten-3beta-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866305
Synonyms
ValueSource
4alpha-(Hydroxymethyl)-4-methyl-5alpha-cholest-8-en-3beta-olChEBI
4alpha-Hydroxymethyl-4beta-methyl-5alpha-cholest-8-en-3beta-olChEBI
4a-(Hydroxymethyl)-4-methyl-5a-cholest-8-en-3b-olGenerator
4Α-(hydroxymethyl)-4-methyl-5α-cholest-8-en-3β-olGenerator
4a-Hydroxymethyl-4b-methyl-5a-cholest-8-en-3b-olGenerator
4Α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-olGenerator
4a-Hydroxymethyl-4b-methyl-5a-8-cholesten-3b-olGenerator
4Α-hydroxymethyl-4β-methyl-5α-8-cholesten-3β-olGenerator
Chemical FormulaC29H50O2
Average Molecular Weight430.717
Monoisotopic Molecular Weight430.38108085
IUPAC Name(2S,5S,6R,7R,11R,14R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,6R,7R,11R,14R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
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)(CO)[C@]1([H])CC3
InChI Identifier
InChI=1S/C29H50O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h19-20,22-23,25-26,30-31H,7-18H2,1-6H3/t20-,22-,23+,25-,26+,27-,28-,29+/m1/s1
InChI KeyUVSRXDFMOZKKGE-WKYRUEGDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0011 g/lALOGPS
LogP6.29ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.29ALOGPS
logP6.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.99 m³·mol⁻¹ChemAxon
Polarizability55.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.47731661259
DarkChem[M-H]-195.5631661259
DeepCCS[M-2H]-238.5430932474
DeepCCS[M+Na]+212.63530932474
AllCCS[M+H]+210.732859911
AllCCS[M+H-H2O]+208.932859911
AllCCS[M+NH4]+212.332859911
AllCCS[M+Na]+212.832859911
AllCCS[M-H]-207.232859911
AllCCS[M+Na-2H]-209.632859911
AllCCS[M+HCOO]-212.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol[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)(CO)[C@]1([H])CC32691.9Standard polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol[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)(CO)[C@]1([H])CC33476.1Standard non polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol[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)(CO)[C@]1([H])CC33581.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol,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)(CO)[C@@H]1CC33420.6Semi standard non polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@](C)(CO[Si](C)(C)C)[C@@H]1CC33396.5Semi standard non polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol,2TMS,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)(CO[Si](C)(C)C)[C@@H]1CC33378.0Semi standard non polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol,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)(CO)[C@@H]1CC33657.6Semi standard non polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@](C)(CO[Si](C)(C)C(C)(C)C)[C@@H]1CC33641.8Semi standard non polar33892256
4??-hydroxymethyl-4??-methyl-5??-cholesta-8-en-3??-ol,2TBDMS,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)(CO[Si](C)(C)C(C)(C)C)[C@@H]1CC33870.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0i00-3016900000-ab3e529fef0b0b6bc74c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol GC-MS (2 TMS) - 70eV, Positivesplash10-08fs-3101390000-e98dc85fd15b3dfd42592017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 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 - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 10V, Positive-QTOFsplash10-03e9-0003900000-859fa2e6192485c5f81d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 20V, Positive-QTOFsplash10-08fs-4139600000-0587ba2fd781412079472017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 40V, Positive-QTOFsplash10-0a4l-6539300000-3007858fd17a652e7f222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 10V, Negative-QTOFsplash10-004i-0001900000-c1917f0711e0ae853c692017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 20V, Negative-QTOFsplash10-01u1-0008900000-09a21da797853708753c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 40V, Negative-QTOFsplash10-001i-0009000000-57a536ae23b1dd6fca8b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 10V, Positive-QTOFsplash10-001i-0004900000-01e87cebab812ea696902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 20V, Positive-QTOFsplash10-0201-5318900000-c998dddf8fa46392bb672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 40V, Positive-QTOFsplash10-06dl-9334000000-672bed4bf348bc3d8d782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 10V, Negative-QTOFsplash10-004i-0000900000-d3ddef81c134412455e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 20V, Negative-QTOFsplash10-004i-0000900000-d3ddef81c134412455e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 40V, Negative-QTOFsplash10-004i-0005900000-8fbb954829347e9daa3b2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-8611
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44263321
PDB IDNot Available
ChEBI ID87045
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 References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.