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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:28:50 UTC

Update Date

2022-03-07 02:54:53 UTC

HMDB ID

HMDB0036346

Secondary Accession Numbers

HMDB36346

Metabolite Identification

Common Name

7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid

Description

7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid, also known as 7-hydroxy-2-methyl-4-oxo-4H-chromene-5-carboxylate, belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid has been detected, but not quantified in, green vegetables. This could make 7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid.

Structure

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

  Mrv0541 05061309052D          

 16 17  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    0.0000    0.0000 C   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
    1.4289    0.0000    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  2  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16  5  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036346

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2=C(C=C(O)C=C2O1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O5/c1-5-2-8(13)10-7(11(14)15)3-6(12)4-9(10)16-5/h2-4,12H,1H3,(H,14,15)

> <INCHI_KEY>
ZCNVIPLKMDPDHM-UHFFFAOYSA-N

> <FORMULA>
C11H8O5

> <MOLECULAR_WEIGHT>
220.1782

> <EXACT_MASS>
220.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.691006597306952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-2-methyl-4-oxo-4H-chromene-5-carboxylic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.2255708556666667

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.577839683018072

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.593402456756753

> <JCHEM_PKA_STRONGEST_BASIC>
-5.34527796753798

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
56.344300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-2-methyl-4-oxochromene-5-carboxylic 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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   0.000   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
HETATM   15  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5    8                                                       
CONECT    3    6    7                                                       
CONECT    4    6    9                                                       
CONECT    5    1    2   16                                                  
CONECT    6    3    4   12                                                  
CONECT    7    3   10   11                                                  
CONECT    8    2   10   13                                                  
CONECT    9    4   10   16                                                  
CONECT   10    7    8    9                                                  
CONECT   11    7   14   15                                                  
CONECT   12    6                                                            
CONECT   13    8                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
CONECT   16    5    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylate	Generator
7-Hydroxy-2-methyl-4-oxo-4H-chromene-5-carboxylate	HMDB

Chemical Formula

C₁₁H₈O₅

Average Molecular Weight

220.1782

Monoisotopic Molecular Weight

220.037173366

IUPAC Name

7-hydroxy-2-methyl-4-oxo-4H-chromene-5-carboxylic acid

Traditional Name

7-hydroxy-2-methyl-4-oxochromene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(C=C(O)C=C2O1)C(O)=O

InChI Identifier

InChI=1S/C11H8O5/c1-5-2-8(13)10-7(11(14)15)3-6(12)4-9(10)16-5/h2-4,12H,1H3,(H,14,15)

InChI Key

ZCNVIPLKMDPDHM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Hydroxybenzoic acid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036346)
Cytoplasm (HMDB: HMDB0036346)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036346)

Source

Exogenous

Exogenous (HMDB: HMDB0036346)

Food

Food (HMDB: HMDB0036346)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0036346)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036346)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.34 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.23	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.34 m³·mol⁻¹	ChemAxon
Polarizability	20.69 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]+	147.632	31661259
DarkChem	[M-H]-	147.226	31661259
DeepCCS	[M+H]+	149.249	30932474
DeepCCS	[M-H]-	146.853	30932474
DeepCCS	[M-2H]-	179.986	30932474
DeepCCS	[M+Na]+	155.3	30932474
AllCCS	[M+H]+	145.8	32859911
AllCCS	[M+H-H2O]+	141.6	32859911
AllCCS	[M+NH4]+	149.8	32859911
AllCCS	[M+Na]+	150.9	32859911
AllCCS	[M-H]-	144.9	32859911
AllCCS	[M+Na-2H]-	144.7	32859911
AllCCS	[M+HCOO]-	144.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid	CC1=CC(=O)C2=C(C=C(O)C=C2O1)C(O)=O	3117.0	Standard polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid	CC1=CC(=O)C2=C(C=C(O)C=C2O1)C(O)=O	1965.3	Standard non polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid	CC1=CC(=O)C2=C(C=C(O)C=C2O1)C(O)=O	2311.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid,1TMS,isomer #1	CC1=CC(=O)C2=C(C(=O)O)C=C(O[Si](C)(C)C)C=C2O1	2263.2	Semi standard non polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid,1TMS,isomer #2	CC1=CC(=O)C2=C(C(=O)O[Si](C)(C)C)C=C(O)C=C2O1	2219.4	Semi standard non polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid,2TMS,isomer #1	CC1=CC(=O)C2=C(C(=O)O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C2O1	2313.9	Semi standard non polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid,1TBDMS,isomer #1	CC1=CC(=O)C2=C(C(=O)O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2525.3	Semi standard non polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid,1TBDMS,isomer #2	CC1=CC(=O)C2=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(O)C=C2O1	2480.3	Semi standard non polar	33892256
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid,2TBDMS,isomer #1	CC1=CC(=O)C2=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2789.0	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 - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-1970000000-60ea2013d75503c81f6c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8094000000-f6ef458f250b4cc7a85d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-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 - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 10V, Positive-QTOF	splash10-00di-0390000000-f8128698d10ecc6fbc34	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 20V, Positive-QTOF	splash10-004i-0950000000-07e612ac07575cd7e9ba	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 40V, Positive-QTOF	splash10-056r-0900000000-24a0f86ba7b0bb6bfd3b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 10V, Negative-QTOF	splash10-014i-0390000000-5dab99c3ae9805e83726	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 20V, Negative-QTOF	splash10-00or-0950000000-fcb3d0949e1009ff5802	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 40V, Negative-QTOF	splash10-002r-3900000000-84f6cee8916d5c461ff8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 10V, Positive-QTOF	splash10-0udi-0090000000-7774c04d84d1e43b1833	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 20V, Positive-QTOF	splash10-0fk9-0090000000-9dfa7e71b4ce9532affb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 40V, Positive-QTOF	splash10-0fsr-1900000000-ad9e5465f0f3f9c57084	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 10V, Negative-QTOF	splash10-014i-0490000000-159a7e59ad59891998a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 20V, Negative-QTOF	splash10-004i-0910000000-c72ea62f35880eadce7a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid 40V, Negative-QTOF	splash10-017s-2900000000-d7101d93f147ac2f8a57	2021-09-24	Wishart 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

FDB015217

KNApSAcK ID

Not Available

Chemspider ID

4474940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315688

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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.. .

Showing metabocard for 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid (HMDB0036346)

MOL for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

3D MOL for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

3D SDF for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

3D-SDF for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

PDB for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

3D PDB for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

SMILES for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

INCHI for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

Structure for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

3D Structure for HMDB0036346 (7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra