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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:18 UTC
Update Date2020-02-26 21:37:02 UTC
HMDB IDHMDB0012165
Secondary Accession Numbers
  • HMDB12165
Metabolite Identification
Common Name4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol
Description4alpha-carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol. It is also a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and can be generated from the enzymatic carboxylation of 4alpha-methyl-5alpha-cholesta-8-en-3-one. 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?1582753022
Synonyms
ValueSource
4a-Carboxy-4b-methyl-5a-cholesta-8-en-3b-olGenerator
4Α-carboxy-4β-methyl-5α-cholesta-8-en-3β-olGenerator
4a-Carboxy-4beta-methyl-5a-cholesta-8-en-3beta-olHMDB
4alpha-Carboxy-4b-methyl-5alpha-cholesta-8-en-3b-olHMDB
(2S,5S,6S,15R)-5-Hydroxy-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylateGenerator
Chemical FormulaC29H48O3
Average Molecular Weight444.6896
Monoisotopic Molecular Weight444.360345402
IUPAC Name(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
Traditional Name(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O
InChI Identifier
InChI=1S/C29H48O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h18-19,21-22,24-25,30H,7-17H2,1-6H3,(H,31,32)/t19?,21?,22?,24?,25-,27+,28+,29-/m0/s1
InChI KeyGLCDBDRQLZKKOJ-XQTRBMGCSA-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
  • 4-carboxy steroid
  • Steroid acid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 15-hydroxysteroid
  • Steroid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP6.82ALOGPS
logP7ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.94 m³·mol⁻¹ChemAxon
Polarizability55.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xr-1009600000-218f2e8215c950df3ac7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3001290000-b4abb9bc6f63998dba1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0002900000-cecfa0f4033bf3bdf954Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7j-4009800000-a4c68b0092c77b998c0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6239200000-ddf379dda298914e4227Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003900000-f421950834a235d62ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000w-0009500000-aaf74005758f1f8e1526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1009200000-3569c0a5ed13ef7146c4Spectrum
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 IDFDB028819
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25202944
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.