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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:24:36 UTC
Update Date2022-03-07 02:55:38 UTC
HMDB IDHMDB0038126
Secondary Accession Numbers
  • HMDB38126
Metabolite Identification
Common NameGenipinic acid
DescriptionGenipinic acid, also known as genipinate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Genipinic acid has been detected, but not quantified in, beverages and fruits. This could make genipinic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Genipinic acid.
Structure
Data?1563863144
Synonyms
ValueSource
GenipinateGenerator
2-{3-hydroxy-1H,3H,4H,5H,6H-cyclopenta[c]furan-4-yl}-3-methoxy-3-oxopropanoateHMDB
Chemical FormulaC11H14O6
Average Molecular Weight242.2253
Monoisotopic Molecular Weight242.07903818
IUPAC Name2-{3-hydroxy-1H,3H,4H,5H,6H-cyclopenta[c]furan-4-yl}-3-methoxy-3-oxopropanoic acid
Traditional Name2-{3-hydroxy-1H,3H,4H,5H,6H-cyclopenta[c]furan-4-yl}-3-methoxy-3-oxopropanoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)C(C1CCC2=C1C(O)OC2)C(O)=O
InChI Identifier
InChI=1S/C11H14O6/c1-16-10(14)8(9(12)13)6-3-2-5-4-17-11(15)7(5)6/h6,8,11,15H,2-4H2,1H3,(H,12,13)
InChI KeyXNIJPPBKASPAIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Dihydrofuran
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
Water Solubility45.2 g/LALOGPS
logP-0.34ALOGPS
logP-0.12ChemAxon
logS-0.73ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.63 m³·mol⁻¹ChemAxon
Polarizability23.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.76831661259
DarkChem[M-H]-153.28331661259
DeepCCS[M+H]+150.53330932474
DeepCCS[M-H]-148.17530932474
DeepCCS[M-2H]-181.65630932474
DeepCCS[M+Na]+156.62630932474
AllCCS[M+H]+152.832859911
AllCCS[M+H-H2O]+149.132859911
AllCCS[M+NH4]+156.232859911
AllCCS[M+Na]+157.232859911
AllCCS[M-H]-153.232859911
AllCCS[M+Na-2H]-153.332859911
AllCCS[M+HCOO]-153.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Genipinic acidCOC(=O)C(C1CCC2=C1C(O)OC2)C(O)=O3408.6Standard polar33892256
Genipinic acidCOC(=O)C(C1CCC2=C1C(O)OC2)C(O)=O1798.3Standard non polar33892256
Genipinic acidCOC(=O)C(C1CCC2=C1C(O)OC2)C(O)=O1899.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Genipinic acid,1TMS,isomer #1COC(=O)C(C(=O)O)C1CCC2=C1C(O[Si](C)(C)C)OC21980.2Semi standard non polar33892256
Genipinic acid,1TMS,isomer #2COC(=O)C(C(=O)O[Si](C)(C)C)C1CCC2=C1C(O)OC21911.9Semi standard non polar33892256
Genipinic acid,2TMS,isomer #1COC(=O)C(C(=O)O[Si](C)(C)C)C1CCC2=C1C(O[Si](C)(C)C)OC22010.8Semi standard non polar33892256
Genipinic acid,1TBDMS,isomer #1COC(=O)C(C(=O)O)C1CCC2=C1C(O[Si](C)(C)C(C)(C)C)OC22195.7Semi standard non polar33892256
Genipinic acid,1TBDMS,isomer #2COC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CCC2=C1C(O)OC22138.7Semi standard non polar33892256
Genipinic acid,2TBDMS,isomer #1COC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C1CCC2=C1C(O[Si](C)(C)C(C)(C)C)OC22416.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Genipinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-5940000000-401fd8fcf26ae8f292532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Genipinic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00rj-9334000000-d0214f774bf52bd2bf1c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Genipinic acid 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 - Genipinic acid 10V, Positive-QTOFsplash10-002f-0790000000-4de907b36993e4700b972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 20V, Positive-QTOFsplash10-004i-0950000000-c35064ade2064ed2b8cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 40V, Positive-QTOFsplash10-00tr-2900000000-b6cedd5451992e7e40aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 10V, Negative-QTOFsplash10-0005-0940000000-e1ed9f4f359895ac3fc82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 20V, Negative-QTOFsplash10-014j-0900000000-fc54ee450c2fe0f353d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 40V, Negative-QTOFsplash10-0550-3900000000-dd3f3790dae46d3606aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 10V, Negative-QTOFsplash10-014l-0980000000-9ca18331510fc445949a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 20V, Negative-QTOFsplash10-00kr-1920000000-9b2a475251f5cd5edfa02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 40V, Negative-QTOFsplash10-00mo-9500000000-a1c510483e4906dfca972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 10V, Positive-QTOFsplash10-002f-0390000000-f187cdbd5c4d2a8de6662021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 20V, Positive-QTOFsplash10-056s-5920000000-c55600ec0b42b0d7e5622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Genipinic acid 40V, Positive-QTOFsplash10-03dv-9800000000-b82971b2a4ef294f6d442021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB017353
KNApSAcK IDC00010563
Chemspider ID35014515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12310086
PDB IDNot Available
ChEBI ID172481
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .