NP-MRD: Showing NP-Card for N-Benzoylanthranilic acid (NP0055013)

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Record Information

Version

2.0

Created at

2022-04-28 01:11:13 UTC

Updated at

2022-04-28 01:11:13 UTC

NP-MRD ID

NP0055013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Benzoylanthranilic acid

Description

N-Benzoylanthranilic acid, also known as 2-(benzoylamino)benzoic acid or 2'-carboxybenzanilide, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. An amidobenzoic acid comprising benzoic acid having a benzamido group at the 2-position. N-Benzoylanthranilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Benzoylanthranilic acid is a fruity tasting compound. N-Benzoylanthranilic acid is found in Dianthus caryophyllus . Outside of the human body,.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    0.9636    1.0807    1.7869 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507    0.4317    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    0.0695    0.0326 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.3555    0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8626    1.0501    1.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1739    1.3189    1.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2100    0.9105    1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244    0.2250   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -0.0680   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.8005   -1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3634   -1.1624   -2.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -1.1540   -2.3733 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945    0.0522    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703   -0.3348   -1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7654   -0.6851   -1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398   -0.6556   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6513   -0.2650    0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987    0.0771    1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567   -0.4807   -0.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755    1.3911    2.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4162    1.8696    2.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2623    1.1191    1.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -0.1087   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324   -2.0987   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -0.3747   -1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872   -0.9885   -2.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8432   -0.9350   -0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4905   -0.2310    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    0.3917    2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4  9  1  0
 18 13  1  0
 12 24  1  0
  8 23  1  0
  7 22  1  0
  6 21  1  0
  5 20  1  0
  3 19  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
M  END


  Mrv0541 02241220532D          

 18 19  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 O   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
   -1.4289    0.8250    0.0000 N   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   -0.4125    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
   -1.4289   -1.6500    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   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
   -2.8579    0.0000    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
   -4.2868    0.0000    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    1.2375    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  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
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO3/c16-13(10-6-2-1-3-7-10)15-12-9-5-4-8-11(12)14(17)18/h1-9H,(H,15,16)(H,17,18)

> <INCHI_KEY>
WXVLIIDDWFGYCV-UHFFFAOYSA-N

> <FORMULA>
C14H11NO3

> <MOLECULAR_WEIGHT>
241.242

> <EXACT_MASS>
241.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.620339910485843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-benzamidobenzoic acid

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.3727135296666657

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.816783804541084

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5513978455365334

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9950556556670116

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
68.84770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-benzoylanthranilic 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      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.667   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
2'-Carboxybenzanilide	ChEBI
2-(Benzoylamino)benzoic acid	ChEBI
Dianthramid b	ChEBI
O-Benzamidobenzoic acid	ChEBI
2-Benzoylaminobenzoic acid	Kegg
2-(Benzoylamino)benzoate	Generator
O-Benzamidobenzoate	Generator
2-Benzoylaminobenzoate	Generator
N-Benzoylanthranilate	Generator
2-(Benzoylamino)-benzoic acid	HMDB
2-Benzamido-benzoic acid	HMDB
2-Benzamidobenzoic acid	HMDB
2-Benzoylamino-benzoic acid	HMDB
2-[(Phenylcarbonyl)amino]benzoic acid	HMDB

Chemical Formula

C₁₄H₁₁NO₃

Average Mass

241.2420 Da

Monoisotopic Mass

241.07389 Da

IUPAC Name

2-benzamidobenzoic acid

Traditional Name

N-benzoylanthranilic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H11NO3/c16-13(10-6-2-1-3-7-10)15-12-9-5-4-8-11(12)14(17)18/h1-9H,(H,15,16)(H,17,18)

InChI Key

WXVLIIDDWFGYCV-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
Dianthus caryophyllus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acids

Alternative Parents

Substituents

Benzoic acid
Benzoyl
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amidobenzoic acid (CHEBI:50037 )

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	2.64	ALOGPS
logP	3.37	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.85 m³·mol⁻¹	ChemAxon
Polarizability	24.62 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