NP-MRD: Showing NP-Card for 5-(Carboxymethyl)-7-hydroxy-2-methylchromone (NP0085015)

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Record Information

Version

1.0

Created at

2022-04-29 05:36:07 UTC

Updated at

2022-04-29 05:36:07 UTC

NP-MRD ID

NP0085015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(Carboxymethyl)-7-hydroxy-2-methylchromone

Description

7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid, also known as 5-(carboxymethyl)-7-hydroxy-2-methylchromone, 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-acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid has been detected, but not quantified in, green vegetables. 5-(Carboxymethyl)-7-hydroxy-2-methylchromone is found in Fallopia multiflora and Rheum sp.. This could make 7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311492D          

 17 18  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    4.2868    0.8250    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
    3.5724   -0.4125    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
    3.5724    1.2375    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
    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 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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
  6  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17  6  1  0  0  0  0
 17 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085015

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O5/c1-6-2-9(14)12-7(4-11(15)16)3-8(13)5-10(12)17-6/h2-3,5,13H,4H2,1H3,(H,15,16)

> <INCHI_KEY>
AWGUDSPRBOCEJK-UHFFFAOYSA-N

> <FORMULA>
C12H10O5

> <MOLECULAR_WEIGHT>
234.2048

> <EXACT_MASS>
234.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
22.412442084567644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(7-hydroxy-2-methyl-4-oxo-4H-chromen-5-yl)acetic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.2057362369999998

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.472212264980045

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.397845575236327

> <JCHEM_PKA_STRONGEST_BASIC>
-5.338089385731084

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
60.39570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7-hydroxy-2-methyl-4-oxochromen-5-yl)acetic 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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6    9                                                       
CONECT    3    7    8                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    1    2   17                                                  
CONECT    7    3    4   12                                                  
CONECT    8    3    5   13                                                  
CONECT    9    2   12   14                                                  
CONECT   10    5   12   17                                                  
CONECT   11    4   15   16                                                  
CONECT   12    7    9   10                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetate	Generator
5-(Carboxymethyl)-7-hydroxy-2-methylchromone	HMDB
7-Hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid, 9ci	HMDB
2-(7-Hydroxy-2-methyl-4-oxo-4H-chromen-5-yl)acetate	Generator

Chemical Formula

C₁₂H₁₀O₅

Average Mass

234.2048 Da

Monoisotopic Mass

234.05282 Da

IUPAC Name

2-(7-hydroxy-2-methyl-4-oxo-4H-chromen-5-yl)acetic acid

Traditional Name

(7-hydroxy-2-methyl-4-oxochromen-5-yl)acetic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O

InChI Identifier

InChI=1S/C12H10O5/c1-6-2-9(14)12-7(4-11(15)16)3-8(13)5-10(12)17-6/h2-3,5,13H,4H2,1H3,(H,15,16)

InChI Key

AWGUDSPRBOCEJK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fallopia multiflora	LOTUS Database	35616633
Rheum sp.	Plant	KNApSAcK

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.46	ALOGPS
logP	1.21	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.4	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	2	ChemAxon
Refractivity	60.4 m³·mol⁻¹	ChemAxon
Polarizability	22.41 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

External Links

HMDB ID

HMDB0040408

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020140

KNApSAcK ID

Not Available

Chemspider ID

20478900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14429402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-(Carboxymethyl)-7-hydroxy-2-methylchromone (NP0085015)

MOL for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

3D MOL for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

3D SDF for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

3D-SDF for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

PDB for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

3D PDB for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

SMILES for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

INCHI for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

Structure for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)

3D Structure for NP0085015 (5-(Carboxymethyl)-7-hydroxy-2-methylchromone)