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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:49 UTC
Update Date2023-02-21 17:22:50 UTC
HMDB IDHMDB0032944
Secondary Accession Numbers
  • HMDB32944
Metabolite Identification
Common NameCoumarin-4-carboxylic acid
DescriptionCoumarin-4-carboxylic acid, also known as 2-oxo-2H-chromene-4-carboxylate, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Coumarin-4-carboxylic acid has been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), red tea, green tea, herbal tea, and herbs and spices. This could make coumarin-4-carboxylic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Coumarin-4-carboxylic acid.
Structure
Data?1677000170
Synonyms
ValueSource
Coumarin-4-carboxylateGenerator
2-oxo-2H-Chromene-4-carboxylateHMDB
Chemical FormulaC10H6O4
Average Molecular Weight190.1522
Monoisotopic Molecular Weight190.02660868
IUPAC Name2-oxo-2H-chromene-4-carboxylic acid
Traditional Nametrans-p-coumarinic acid
CAS Registry Number27393-46-0
SMILES
OC(=O)C1=CC(=O)OC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H6O4/c11-9-5-7(10(12)13)6-3-1-2-4-8(6)14-9/h1-5H,(H,12,13)
InChI KeyDORZTUIRBJRLFD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility3226 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.64 g/LALOGPS
logP1.43ALOGPS
logP1.27ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability17.45 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]+140.09131661259
DarkChem[M-H]-139.53731661259
DeepCCS[M-2H]-168.20730932474
DeepCCS[M+Na]+142.87430932474
AllCCS[M+H]+138.532859911
AllCCS[M+H-H2O]+134.132859911
AllCCS[M+NH4]+142.732859911
AllCCS[M+Na]+143.932859911
AllCCS[M-H]-135.832859911
AllCCS[M+Na-2H]-135.932859911
AllCCS[M+HCOO]-136.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Coumarin-4-carboxylic acidOC(=O)C1=CC(=O)OC2=CC=CC=C122849.4Standard polar33892256
Coumarin-4-carboxylic acidOC(=O)C1=CC(=O)OC2=CC=CC=C121685.3Standard non polar33892256
Coumarin-4-carboxylic acidOC(=O)C1=CC(=O)OC2=CC=CC=C121889.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Coumarin-4-carboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(=O)OC2=CC=CC=C122023.8Semi standard non polar33892256
Coumarin-4-carboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)OC2=CC=CC=C122292.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Coumarin-4-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vp-2900000000-942870ef7f88f3150cda2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coumarin-4-carboxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9640000000-9dfaeb2ef54ada1471ec2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coumarin-4-carboxylic 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 - Coumarin-4-carboxylic acid 10V, Positive-QTOFsplash10-0006-0900000000-35d0acc3fcef778fdfb52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Positive-QTOFsplash10-0006-0900000000-fe39a65a64ced820c94c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Positive-QTOFsplash10-0005-3900000000-2f8d9579b95064ce734f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Negative-QTOFsplash10-000i-0900000000-5974103032b5db02767a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Negative-QTOFsplash10-000b-0900000000-0bc53741f85bddef20082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Negative-QTOFsplash10-0udm-9800000000-c2030b1e560570fc4ad92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Negative-QTOFsplash10-0002-0900000000-1d0db45cb6de82902a082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Negative-QTOFsplash10-0002-0900000000-1d0db45cb6de82902a082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Negative-QTOFsplash10-0005-3900000000-78037863f002472855cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Positive-QTOFsplash10-00di-0900000000-88ad64733160b68872cb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Positive-QTOFsplash10-00di-0900000000-5bbdba0cddbf6a01d78b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Positive-QTOFsplash10-0gb9-2900000000-738f8fb6c88d557645c92021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB010929
KNApSAcK IDC00055433
Chemspider ID526226
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound605378
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1832581
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Coumarin-4-carboxylic acid → 3,4,5-trihydroxy-6-(2-oxo-2H-chromene-4-carbonyloxy)oxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Coumarin-4-carboxylic acid → 2-{[hydroxy(2-oxo-2H-chromen-4-yl)methylidene]amino}acetic aciddetails