NP-MRD: Showing NP-Card for 2-[(Carboxyacetyl)amino]benzoic acid (NP0084593)

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Record Information

Version

2.0

Created at

2022-04-29 05:17:28 UTC

Updated at

2022-04-29 05:17:28 UTC

NP-MRD ID

NP0084593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(Carboxyacetyl)amino]benzoic acid

Description

2-(Malonylamino)benzoic acid, also known as N-malonylanthranilic acid, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. 2-(Malonylamino)benzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(Malonylamino)benzoic acid has been detected, but not quantified in, nuts. 2-[(Carboxyacetyl)amino]benzoic acid is found in Arachis hypogaea . This could make 2-(malonylamino)benzoic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241218202D          

 16 16  0  0  0  0            999 V2000
    0.4006   -0.6016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -1.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -1.8054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426   -0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -1.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4070   -0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4070    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426    0.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    0.6016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3203    1.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7649    1.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7649    1.8054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3203    1.8054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4070    0.6016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(=O)NC1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO5/c12-8(5-9(13)14)11-7-4-2-1-3-6(7)10(15)16/h1-4H,5H2,(H,11,12)(H,13,14)(H,15,16)

> <INCHI_KEY>
ZDSSCYCDBASEJQ-UHFFFAOYSA-N

> <FORMULA>
C10H9NO5

> <MOLECULAR_WEIGHT>
223.1822

> <EXACT_MASS>
223.048072403

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.376748585669453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-carboxyacetamido)benzoic acid

> <ALOGPS_LOGP>
0.26

> <JCHEM_LOGP>
1.4107675373333333

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.189806571049587

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.185358683446645

> <JCHEM_PKA_STRONGEST_BASIC>
-7.883640938554963

> <JCHEM_POLAR_SURFACE_AREA>
103.7

> <JCHEM_REFRACTIVITY>
54.52130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-malonylanthranilic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.748  -1.123   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.598  -1.872   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.598  -3.370   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.946  -1.123   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.145  -1.872   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.493  -1.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.493   0.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.145   1.123   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.946   0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.598   1.123   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.598   1.872   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.946   1.123   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.294   1.872   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.294   3.370   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.598   3.370   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.493   1.123   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13                                                            
CONECT   15   11                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
2-(Malonylamino)benzoate	Generator
2-[(2-Carboxyacetyl)amino]benzenecarboxylic acid	HMDB
2-[(Carboxyacetyl)amino]benzoic acid, 9ci	HMDB
N-Malonylanthranilic acid	HMDB
N-Malonylanthranilate	Generator

Chemical Formula

C₁₀H₉NO₅

Average Mass

223.1822 Da

Monoisotopic Mass

223.04807 Da

IUPAC Name

2-(2-carboxyacetamido)benzoic acid

Traditional Name

N-malonylanthranilic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(=O)NC1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C10H9NO5/c12-8(5-9(13)14)11-7-4-2-1-3-6(7)10(15)16/h1-4H,5H2,(H,11,12)(H,13,14)(H,15,16)

InChI Key

ZDSSCYCDBASEJQ-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
Arachis hypogaea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
Benzoic acid
Anilide
Benzoyl
N-arylamide
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dicarboxylic acid monoamide (CHEBI:52430 )

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	0.26	ALOGPS
logP	1.41	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	-7.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.52 m³·mol⁻¹	ChemAxon
Polarizability	20.38 Å³	ChemAxon
Number of Rings	1	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

HMDB0039495

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019102

KNApSAcK ID

Not Available

Chemspider ID

388954

KEGG Compound ID

C03147

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439922

PDB ID

Not Available

ChEBI ID

52430

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-[(Carboxyacetyl)amino]benzoic acid (NP0084593)

MOL for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

3D MOL for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

3D SDF for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

3D-SDF for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

PDB for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

3D PDB for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

SMILES for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

INCHI for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

Structure for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)

3D Structure for NP0084593 (2-[(Carboxyacetyl)amino]benzoic acid)