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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:01:35 UTC
Update Date2022-03-07 02:55:05 UTC
HMDB IDHMDB0036847
Secondary Accession Numbers
  • HMDB36847
Metabolite Identification
Common NameColubrinic acid
DescriptionColubrinic acid, also known as colubrinate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Colubrinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862937
Synonyms
ValueSource
ColubrinateGenerator
Zizyberanalic acidHMDB
15-Formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylateGenerator
Chemical FormulaC30H46O4
Average Molecular Weight470.6838
Monoisotopic Molecular Weight470.33960996
IUPAC Name15-formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylic acid
Traditional Name15-formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylic acid
CAS Registry Number67594-73-4
SMILES
CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)C(C=O)C(O)C(C)(C)C5CCC34C)C12)C(O)=O
InChI Identifier
InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-27(5)19(23(18)30)8-9-22-28(27,6)12-11-21-26(3,4)24(32)20(16-31)29(21,22)7/h16,18-24,32H,1,8-15H2,2-7H3,(H,33,34)
InChI KeySLWJVQQNDGLXTK-UHFFFAOYSA-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
  • Steroid acid
  • 3-carboxy steroid
  • 18-oxosteroid
  • 18-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 16-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Aldehyde
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point282 - 284 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0006 g/LALOGPS
logP5.08ALOGPS
logP5.42ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity133.18 m³·mol⁻¹ChemAxon
Polarizability54.68 ųChemAxon
Number of Rings5ChemAxon
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]+208.73431661259
DarkChem[M-H]-203.03431661259
DeepCCS[M-2H]-244.38830932474
DeepCCS[M+Na]+219.95430932474
AllCCS[M+H]+213.332859911
AllCCS[M+H-H2O]+211.732859911
AllCCS[M+NH4]+214.932859911
AllCCS[M+Na]+215.332859911
AllCCS[M-H]-215.432859911
AllCCS[M+Na-2H]-217.232859911
AllCCS[M+HCOO]-219.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Colubrinic acidCC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)C(C=O)C(O)C(C)(C)C5CCC34C)C12)C(O)=O3107.0Standard polar33892256
Colubrinic acidCC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)C(C=O)C(O)C(C)(C)C5CCC34C)C12)C(O)=O3491.4Standard non polar33892256
Colubrinic acidCC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)C(C=O)C(O)C(C)(C)C5CCC34C)C12)C(O)=O3738.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Colubrinic acid,1TMS,isomer #1C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)C(C=O)C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123794.3Semi standard non polar33892256
Colubrinic acid,1TMS,isomer #2C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)C(C=O)C(O)C(C)(C)C5CCC43C)C123724.9Semi standard non polar33892256
Colubrinic acid,1TMS,isomer #3C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C)C(O)C(C)(C)C5CCC43C)C123767.4Semi standard non polar33892256
Colubrinic acid,2TMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)C(C=O)C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123582.1Semi standard non polar33892256
Colubrinic acid,2TMS,isomer #2C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123722.8Semi standard non polar33892256
Colubrinic acid,2TMS,isomer #3C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C)C(O)C(C)(C)C5CCC43C)C123639.1Semi standard non polar33892256
Colubrinic acid,3TMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123549.4Semi standard non polar33892256
Colubrinic acid,3TMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123599.0Standard non polar33892256
Colubrinic acid,1TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)C(C=O)C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124021.3Semi standard non polar33892256
Colubrinic acid,1TBDMS,isomer #2C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)C(C=O)C(O)C(C)(C)C5CCC43C)C123975.3Semi standard non polar33892256
Colubrinic acid,1TBDMS,isomer #3C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C(C)(C)C)C(O)C(C)(C)C5CCC43C)C124012.6Semi standard non polar33892256
Colubrinic acid,2TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)C(C=O)C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124083.2Semi standard non polar33892256
Colubrinic acid,2TBDMS,isomer #2C=C(C)C1CCC2(C(=O)O)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124202.0Semi standard non polar33892256
Colubrinic acid,2TBDMS,isomer #3C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C(C)(C)C)C(O)C(C)(C)C5CCC43C)C124141.8Semi standard non polar33892256
Colubrinic acid,3TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124266.5Semi standard non polar33892256
Colubrinic acid,3TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)C(=CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124288.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Colubrinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar3-0039800000-89aa9a2e90be413702262017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Colubrinic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-3034393000-d9fa50587124622ec23b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Colubrinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Colubrinic acid 10V, Negative-QTOFsplash10-014i-0000900000-cd319dcb992264c246402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Colubrinic acid 20V, Negative-QTOFsplash10-014i-0000900000-fa1b996e12716755e6442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Colubrinic acid 40V, Negative-QTOFsplash10-014i-0000900000-df3efb935b48f82394382021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 10V, Negative-QTOFsplash10-014i-0000900000-bbc0b60ef32faa80be072015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 20V, Negative-QTOFsplash10-0lfr-0000900000-212a5cd8ce367531dfe52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 40V, Negative-QTOFsplash10-0pbc-2002900000-0124bbe8a7f3ffe8b58f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 10V, Negative-QTOFsplash10-014i-0000900000-eed153c89a68fc831e0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 20V, Negative-QTOFsplash10-014l-0001900000-f30ca310ca833e0138b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 40V, Negative-QTOFsplash10-014i-0002900000-432988c1f2ec1f3f46352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 10V, Positive-QTOFsplash10-0uk9-0000900000-d4a27df66176e1741bb62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 20V, Positive-QTOFsplash10-0zg0-0001900000-1508f0fe53beb11861f42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 40V, Positive-QTOFsplash10-0a4j-2287900000-f4770134575bd17ce4622015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 10V, Positive-QTOFsplash10-00di-0000900000-e059fcfeb15305c8e26d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 20V, Positive-QTOFsplash10-0fi9-0145900000-14022d2f4358f5d1072d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colubrinic acid 40V, Positive-QTOFsplash10-0019-4984000000-f06202c1dc2a0e6aad9f2021-09-22Wishart 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 IDFDB015799
KNApSAcK IDC00032552
Chemspider ID22370281
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14137704
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.