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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:11:59 UTC
Update Date2022-03-07 03:17:53 UTC
HMDB IDHMDB0062383
Secondary Accession Numbers
  • HMDB62383
Metabolite Identification
Common Name4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol
Description4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol, also known as 4alpha-carboxy-4beta-methyl-zymosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol is considered to be a sterol lipid molecule. 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866304
Synonyms
ValueSource
(3beta,4alpha,5alpha)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylic acidChEBI
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
4alpha-Carboxy-4beta-methyl-cholesta-8,24-dien-3beta-olChEBI
4alpha-Carboxy-4beta-methyl-zymosterolChEBI
(3b,4a,5a)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylateGenerator
(3b,4a,5a)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylic acidGenerator
(3beta,4alpha,5alpha)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylateGenerator
(3Β,4α,5α)-3-hydroxy-4-methylcholesta-8,24-diene-4-carboxylateGenerator
(3Β,4α,5α)-3-hydroxy-4-methylcholesta-8,24-diene-4-carboxylic acidGenerator
4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-olGenerator
4a-Carboxy-4b-methyl-cholesta-8,24-dien-3b-olGenerator
4Α-carboxy-4β-methyl-cholesta-8,24-dien-3β-olGenerator
4a-Carboxy-4b-methyl-zymosterolGenerator
4Α-carboxy-4β-methyl-zymosterolGenerator
Chemical FormulaC29H46O3
Average Molecular Weight442.6737
Monoisotopic Molecular Weight442.344695338
IUPAC Name(2S,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
Traditional Name(2S,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(O)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C29H46O3/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/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21-,22+,24-,25+,27-,28-,29+/m1/s1
InChI KeyMYWAIWDQTCHPTH-LJAIZBFVSA-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 Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0022 g/lALOGPS
LogP6.64ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.64ALOGPS
logP6.6ChemAxon
logS-5.3ALOGPS
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 Count5ChemAxon
Refractivity131.79 m³·mol⁻¹ChemAxon
Polarizability54.42 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]+209.54331661259
DarkChem[M-H]-203.83331661259
DeepCCS[M-2H]-246.82130932474
DeepCCS[M+Na]+220.92830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-3??-ol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(O)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C3428.4Standard polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-3??-ol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(O)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C3378.0Standard non polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-3??-ol[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(O)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C3549.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-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)(C(=O)O)[C@@H]1CC33541.7Semi standard non polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-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)(C(=O)O[Si](C)(C)C)[C@@H]1CC33492.0Semi standard non polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-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)(C(=O)O[Si](C)(C)C)[C@@H]1CC33494.6Semi standard non polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-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)(C(=O)O)[C@@H]1CC33768.0Semi standard non polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-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)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC33744.9Semi standard non polar33892256
4??-carboxy-4??-methyl-5??-cholesta-8,24-dien-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)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC33988.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1009500000-659d37e4a554032db6552017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3001290000-49cf623a8c01d727af892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-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-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 10V, Positive-QTOFsplash10-004l-0003900000-f0c6600c4e9f4b0ebe5b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 20V, Positive-QTOFsplash10-004i-1009500000-0b5ddc78f46f99358d6a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 40V, Positive-QTOFsplash10-014r-3139200000-0ffe6baaea219aee2a612016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 10V, Negative-QTOFsplash10-0006-0004900000-3f078b450569105ded832016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 20V, Negative-QTOFsplash10-002e-0009500000-ec62c372df35c30832142016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 40V, Negative-QTOFsplash10-003r-1009200000-7f445ec03fa57924e2f52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 10V, Negative-QTOFsplash10-0006-0000900000-a071385ec6b10bec98022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 20V, Negative-QTOFsplash10-0006-0007900000-a679f216bf445402e2f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 40V, Negative-QTOFsplash10-014r-1009300000-0d8a0e3dbdcfdc36b4052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 10V, Positive-QTOFsplash10-0006-0004900000-6ab84f255513309528922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 20V, Positive-QTOFsplash10-001r-7829500000-6c46f5c397c9c07c620d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol 40V, Positive-QTOFsplash10-0apu-9448000000-f2eb3b928ee415bf05f92021-09-24Wishart 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 ID20059528
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22298938
PDB IDNot Available
ChEBI ID50591
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.