NP-MRD: Showing NP-Card for 2-amino-4-(4-aminobenzamido)benzoic acid (NP0198424)

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Record Information

Version

2.0

Created at

2022-09-04 16:52:18 UTC

Updated at

2022-09-04 16:52:19 UTC

NP-MRD ID

NP0198424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-4-(4-aminobenzamido)benzoic acid

Description

Carotamine belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. Carotamine is a moderately basic compound (based on its pKa). Outside of the human body, Carotamine has been detected, but not quantified in, root vegetables. 2-amino-4-(4-aminobenzamido)benzoic acid is found in Daucus carota. This could make carotamine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -6.6187    0.4899    0.6541 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048    0.3276    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749    0.0046    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.1423    1.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176    0.0240    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9681   -0.1553    0.8577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4976   -0.4417    1.9866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993   -0.0211   -0.2281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999   -0.1722   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781   -0.4391    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4536   -0.5717    0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1166   -0.4456   -0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.5904   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473   -0.4744   -1.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2727   -0.8577    0.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497   -0.1753   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0338   -0.0452   -2.7842 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -0.0472   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    0.3457   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4615    0.5011   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0016    1.3344    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2661   -0.1545    0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.1391    2.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083   -0.3987    2.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5556    0.2209   -1.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6495   -0.5513    1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302   -0.7807    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1902   -0.3925    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790    0.8930   -3.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4760   -0.9074   -3.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300    0.1593   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.4871   -1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9033    0.7595   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 19  1  0
 19 20  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 12 16  1  0
 16 17  1  0
 16 18  2  0
 20  2  1  0
 18  9  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
 19 32  1  0
 20 33  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv0541 02241210402D          

 20 21  0  0  0  0            999 V2000
    2.8553   -1.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553   -1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703   -0.6215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415   -0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265   -1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553    0.6160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0021    0.6160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171    0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -0.6215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253    1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    1.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5703    1.8535    0.0000 N   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  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 13 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0198424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(C=C1)C(=O)NC1=CC=C(C(O)=O)C(N)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H13N3O3/c15-9-3-1-8(2-4-9)13(18)17-10-5-6-11(14(19)20)12(16)7-10/h1-7H,15-16H2,(H,17,18)(H,19,20)

> <INCHI_KEY>
GGUOSFAJMKBDFW-UHFFFAOYSA-N

> <FORMULA>
C14H13N3O3

> <MOLECULAR_WEIGHT>
271.2713

> <EXACT_MASS>
271.095691297

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.99906460505383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-4-(4-aminobenzamido)benzoic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.7148616216666666

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.471886273398066

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.854589063158893

> <JCHEM_PKA_STRONGEST_BASIC>
2.785171220164086

> <JCHEM_POLAR_SURFACE_AREA>
118.43999999999998

> <JCHEM_REFRACTIVITY>
78.2485

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-(4-aminobenzamido)benzoic 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       5.330  -3.470   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.330  -1.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.665  -1.160   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.997  -1.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.997   0.380   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.663   1.150   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.328   0.380   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.328  -1.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.663  -1.930   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.330   1.150   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -0.004   1.150   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -1.339   0.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.671   1.152   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.341  -1.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.661   2.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.990   3.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.330   2.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.330   1.152   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.990   0.372   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -6.665   3.460   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    5                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   15   19                                                  
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   13   18                                                       
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-4-(4-aminobenzoylamino)benzoic acid	HMDB
2-Amino-4-(4-aminobenzamido)benzoate	Generator

Chemical Formula

C₁₄H₁₃N₃O₃

Average Mass

271.2713 Da

Monoisotopic Mass

271.09569 Da

IUPAC Name

2-amino-4-(4-aminobenzamido)benzoic acid

Traditional Name

2-amino-4-(4-aminobenzamido)benzoic acid

CAS Registry Number

Not Available

SMILES

NC1=CC=C(C=C1)C(=O)NC1=CC=C(C(O)=O)C(N)=C1

InChI Identifier

InChI=1S/C14H13N3O3/c15-9-3-1-8(2-4-9)13(18)17-10-5-6-11(14(19)20)12(16)7-10/h1-7H,15-16H2,(H,17,18)(H,19,20)

InChI Key

GGUOSFAJMKBDFW-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Daucus carota	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
Aminobenzoic acid
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoic acid
Aniline or substituted anilines
Benzoyl
Vinylogous amide
Amino acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Primary amine
Amine
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.1	ALOGPS
logP	1.71	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.25 m³·mol⁻¹	ChemAxon
Polarizability	28 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

HMDB0039955

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019618

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-4-(4-aminobenzamido)benzoic acid (NP0198424)

MOL for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

3D MOL for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

3D SDF for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

3D-SDF for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

PDB for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

3D PDB for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

SMILES for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

INCHI for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

Structure for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)

3D Structure for NP0198424 (2-amino-4-(4-aminobenzamido)benzoic acid)