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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:34 UTC
HMDB IDHMDB0059642
Secondary Accession Numbers
  • HMDB59642
Metabolite Identification
Common Name4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol
Description4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563865959
Synonyms
ValueSource
4-b-Hydroxymethyl-4-a-methyl-5-a-cholest-7-en-3-b-olGenerator
4-Β-hydroxymethyl-4-α-methyl-5-α-cholest-7-en-3-β-olGenerator
Chemical FormulaC29H50O2
Average Molecular Weight430.7061
Monoisotopic Molecular Weight430.381080844
IUPAC Name(1R,2R,11R,14R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Name(1R,2R,11R,14R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CCC2C(C)(CO)C(O)CC[C@]12C
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/h10,19-20,22-26,30-31H,7-9,11-18H2,1-6H3/t20-,22-,23+,24+,25?,26?,27-,28-,29?/m1/s1
InChI KeyDWEXIFLNCXYYAA-NGHOBUOVSA-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
  • Cholesterol
  • Diterpenoid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
logP6.95ALOGPS
logP6.58ChemAxon
logS-6.4ALOGPS
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
Refractivity131.26 m³·mol⁻¹ChemAxon
Polarizability55.33 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]+204.68731661259
DarkChem[M-H]-196.64531661259
DeepCCS[M-2H]-242.16430932474
DeepCCS[M+Na]+218.53330932474
AllCCS[M+H]+210.632859911
AllCCS[M+H-H2O]+208.832859911
AllCCS[M+NH4]+212.332859911
AllCCS[M+Na]+212.832859911
AllCCS[M-H]-207.132859911
AllCCS[M+Na-2H]-209.532859911
AllCCS[M+HCOO]-212.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CCC2C(C)(CO)C(O)CC[C@]12C2784.1Standard polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CCC2C(C)(CO)C(O)CC[C@]12C3500.9Standard non polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CCC2C(C)(CO)C(O)CC[C@]12C3622.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4C(C)(CO[Si](C)(C)C)C(O)CC[C@]4(C)[C@H]3CC[C@@]21C3543.5Semi standard non polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4C(C)(CO)C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3576.3Semi standard non polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4C(C)(CO[Si](C)(C)C)C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3541.4Semi standard non polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4C(C)(CO[Si](C)(C)C(C)(C)C)C(O)CC[C@]4(C)[C@H]3CC[C@@]21C3777.6Semi standard non polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4C(C)(CO)C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3783.5Semi standard non polar33892256
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4C(C)(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4007.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gb9-1106900000-74b51fc35552469ef9ba2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol GC-MS (2 TMS) - 70eV, Positivesplash10-0bta-3000290000-e017787e41a54e1e91cd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-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 - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Positive-QTOFsplash10-03e9-0003900000-fefcf197689a399fbacf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Positive-QTOFsplash10-08fs-4139600000-d8da129630e9238f62172017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Positive-QTOFsplash10-0a4l-6449200000-3f19ac27d43f51a372f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Negative-QTOFsplash10-004i-0001900000-c1917f0711e0ae853c692017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Negative-QTOFsplash10-01u1-0008900000-80ef32a1a3dcf90c5e652017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Negative-QTOFsplash10-001i-0009000000-b87880239776161df3e62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Negative-QTOFsplash10-004i-0000900000-d3ddef81c134412455e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Negative-QTOFsplash10-004i-0000900000-d3ddef81c134412455e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Negative-QTOFsplash10-004i-0004900000-f72b27681355470ec0572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 10V, Positive-QTOFsplash10-001i-0004900000-5aa2a3e5822f592f800e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 20V, Positive-QTOFsplash10-0830-8829500000-3673b6b4b45359d618a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol 40V, Positive-QTOFsplash10-0002-9112000000-0673567bb7fab18037362021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769779
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..

Enzymes

General function:
Involved in iron ion binding
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
Q15800
Molecular weight:
19470.325
Reactions
4,4-Dimethyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + Oxygen → 4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)(+) + Waterdetails
4-beta-Hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + Oxygen → 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)(+) + Waterdetails