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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 07:54:46 UTC
Update Date2021-09-24 07:54:46 UTC
HMDB IDHMDB0304192
Secondary Accession NumbersNone
Metabolite Identification
Common Name4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol
Description 4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol can be found in a number of food items such as white lupine, chinese chives, radish, and pear, which makes 4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol a potential biomarker for the consumption of these food products.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H43O3
Average Molecular Weight427.65
Monoisotopic Molecular Weight427.321768825
IUPAC Name5-hydroxy-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylate
Traditional Name5-hydroxy-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylate
CAS Registry NumberNot Available
SMILES
CC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C1CC3)C([O-])=O
InChI Identifier
InChI=1S/C28H44O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h7,18,20-21,23-25,29H,6,8-16H2,1-5H3,(H,30,31)/p-1
InChI KeyJHIWIFRQJXLNEU-UHFFFAOYSA-M
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
  • Steroid acid
  • 4-carboxy steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic anion
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP6.18ALOGPS
logP6.04ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity138.12 m³·mol⁻¹ChemAxon
Polarizability52.24 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
AllCCS[M+H]+209.62932859911
AllCCS[M+H-H2O]+207.62332859911
AllCCS[M+Na]+211.99732859911
AllCCS[M+NH4]+211.47132859911
AllCCS[M-H]-208.69232859911
AllCCS[M+Na-2H]-210.54732859911
AllCCS[M+HCOO]-212.74532859911
DeepCCS[M-2H]-233.97830932474
DeepCCS[M+Na]+209.25130932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol 10V, Negative-QTOFsplash10-0a4i-0003900000-4b0b8b2bff31dda469cd2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol 20V, Negative-QTOFsplash10-067i-0009400000-153e27f2d5fe237a75442019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol 40V, Negative-QTOFsplash10-014i-0019000000-276537ca59497ffb82182019-02-23Wishart 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 IDFDB030522
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74428071
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 ReferencesNot Available