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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:25 UTC
Update Date2021-09-14 15:41:41 UTC
HMDB IDHMDB0012172
Secondary Accession Numbers
  • HMDB12172
Metabolite Identification
Common Name4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol
Description4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from 4-alpha-methylzymosterol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.
Structure
Data?1582753023
Synonyms
ValueSource
4a-Hydroxymethyl-5a-cholesta-8,24-dien-3b-olGenerator
4Α-hydroxymethyl-5α-cholesta-8,24-dien-3β-olGenerator
4 alpha-Hysroxymethyl-5 alpha-cholsta-8,24-dien-3 beta-olHMDB
4-alpha-Hysroxymethyl-5-alpha-cholsta-8,24-dien-3-beta-olHMDB
Chemical FormulaC28H46O2
Average Molecular Weight414.6636
Monoisotopic Molecular Weight414.349780716
IUPAC Name(2S,5S,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
SMILES
CC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC3
InChI Identifier
InChI=1S/C28H46O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,19,21-24,26,29-30H,6,8-17H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1
InChI KeyORZKEIGPXNMCHC-GYISYUOESA-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
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.003 g/LALOGPS
logP10(5.55) g/LALOGPS
logP10(5.63) g/LChemAxon
logS10(-5.1) g/LALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.5 m³·mol⁻¹ChemAxon
Polarizability52.07 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.53131661259
DarkChem[M-H]-188.89931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-olCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC32572.2Standard polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-olCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC33353.2Standard non polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-olCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC33548.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol,1TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](CO)C1CC33411.8Semi standard non polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol,1TMS,isomer #2CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](CO[Si](C)(C)C)C1CC33467.5Semi standard non polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol,2TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)C1CC33454.6Semi standard non polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol,1TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)C1CC33638.0Semi standard non polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol,1TBDMS,isomer #2CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)C1CC33696.2Semi standard non polar33892256
4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol,2TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)C1CC33915.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pa-1009000000-26a6475677afe7b86ff02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol GC-MS (2 TMS) - 70eV, Positivesplash10-0006-3101390000-9a7be192c5b850bae9982017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-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 - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 10V, Positive-QTOFsplash10-00kb-0009200000-6a505952adf6b44c34712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 20V, Positive-QTOFsplash10-00os-2019000000-bfa43bfa929440dc08862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 40V, Positive-QTOFsplash10-07br-3229000000-f36e1263e8ba538a453e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 10V, Negative-QTOFsplash10-03di-0005900000-10de80058b799a204f932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 20V, Negative-QTOFsplash10-03yj-0009300000-6ac3a41026db556615bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 40V, Negative-QTOFsplash10-014i-0009000000-3023571b31cb46c006272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 10V, Negative-QTOFsplash10-03di-0000900000-801eb48ce946466924ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 20V, Negative-QTOFsplash10-03di-0004900000-e378fd1e3979963780412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 40V, Negative-QTOFsplash10-0159-0009100000-ebfff925eb97c38760e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 10V, Positive-QTOFsplash10-014i-1009600000-2c72cfeb5cd28e69d4992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 20V, Positive-QTOFsplash10-053r-5049200000-384720890ef04a94050b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol 40V, Positive-QTOFsplash10-0a5i-9102000000-5354f5963314ff320b292021-09-24Wishart 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 IDFDB028826
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25202625
PDB IDNot Available
ChEBI IDNot Available
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. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
  6. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  8. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..