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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:49 UTC

Update Date

2023-02-21 17:22:50 UTC

HMDB ID

HMDB0032944

Secondary Accession Numbers

HMDB32944

Metabolite Identification

Common Name

Coumarin-4-carboxylic acid

Description

Coumarin-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061306492D          

 14 15  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032944

> <DATABASE_NAME>
hmdb

> <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_KEY>
DORZTUIRBJRLFD-UHFFFAOYSA-N

> <FORMULA>
C10H6O4

> <MOLECULAR_WEIGHT>
190.1522

> <EXACT_MASS>
190.02660868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.445673662148707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-oxo-2H-chromene-4-carboxylic acid

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.2744468193333331

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7200813454416655

> <JCHEM_PKA_STRONGEST_BASIC>
-6.996170406349533

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
47.54780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-p-coumarinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6   10                                                  
CONECT    8    4    6   14                                                  
CONECT    9    5   11   14                                                  
CONECT   10    7   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Coumarin-4-carboxylate	Generator
2-oxo-2H-Chromene-4-carboxylate	HMDB

Chemical Formula

C₁₀H₆O₄

Average Molecular Weight

190.1522

Monoisotopic Molecular Weight

190.02660868

IUPAC Name

2-oxo-2H-chromene-4-carboxylic acid

Traditional Name

trans-p-coumarinic acid

CAS Registry Number

27393-46-0

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 Key

DORZTUIRBJRLFD-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).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032944)
Cytoplasm (HMDB: HMDB0032944)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032944)

Source

Exogenous

Food

Food (HMDB: HMDB0032944)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032944)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032944)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3226 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.64 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.27	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.55 m³·mol⁻¹	ChemAxon
Polarizability	17.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.091	31661259
DarkChem	[M-H]-	139.537	31661259
DeepCCS	[M-2H]-	168.207	30932474
DeepCCS	[M+Na]+	142.874	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	142.7	32859911
AllCCS	[M+Na]+	143.9	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coumarin-4-carboxylic acid	OC(=O)C1=CC(=O)OC2=CC=CC=C12	2849.4	Standard polar	33892256
Coumarin-4-carboxylic acid	OC(=O)C1=CC(=O)OC2=CC=CC=C12	1685.3	Standard non polar	33892256
Coumarin-4-carboxylic acid	OC(=O)C1=CC(=O)OC2=CC=CC=C12	1889.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coumarin-4-carboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(=O)OC2=CC=CC=C12	2023.8	Semi standard non polar	33892256
Coumarin-4-carboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)OC2=CC=CC=C12	2292.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Coumarin-4-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vp-2900000000-942870ef7f88f3150cda	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumarin-4-carboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9640000000-9dfaeb2ef54ada1471ec	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumarin-4-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Positive-QTOF	splash10-0006-0900000000-35d0acc3fcef778fdfb5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Positive-QTOF	splash10-0006-0900000000-fe39a65a64ced820c94c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Positive-QTOF	splash10-0005-3900000000-2f8d9579b95064ce734f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Negative-QTOF	splash10-000i-0900000000-5974103032b5db02767a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Negative-QTOF	splash10-000b-0900000000-0bc53741f85bddef2008	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Negative-QTOF	splash10-0udm-9800000000-c2030b1e560570fc4ad9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Negative-QTOF	splash10-0002-0900000000-1d0db45cb6de82902a08	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Negative-QTOF	splash10-0002-0900000000-1d0db45cb6de82902a08	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Negative-QTOF	splash10-0005-3900000000-78037863f002472855cd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 10V, Positive-QTOF	splash10-00di-0900000000-88ad64733160b68872cb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 20V, Positive-QTOF	splash10-00di-0900000000-5bbdba0cddbf6a01d78b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-4-carboxylic acid 40V, Positive-QTOF	splash10-0gb9-2900000000-738f8fb6c88d557645c9	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010929

KNApSAcK ID

C00055433

Chemspider ID

526226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

605378

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1832581

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

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 acid	details

Enzyme Details

2. Glycine N-acyltransferase

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 acid	details

Showing metabocard for Coumarin-4-carboxylic acid (HMDB0032944)

MOL for HMDB0032944 (Coumarin-4-carboxylic acid)

3D MOL for HMDB0032944 (Coumarin-4-carboxylic acid)

3D SDF for HMDB0032944 (Coumarin-4-carboxylic acid)

3D-SDF for HMDB0032944 (Coumarin-4-carboxylic acid)

PDB for HMDB0032944 (Coumarin-4-carboxylic acid)

3D PDB for HMDB0032944 (Coumarin-4-carboxylic acid)

SMILES for HMDB0032944 (Coumarin-4-carboxylic acid)

INCHI for HMDB0032944 (Coumarin-4-carboxylic acid)

Structure for HMDB0032944 (Coumarin-4-carboxylic acid)

3D Structure for HMDB0032944 (Coumarin-4-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions