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Showing NP-Card for Formylanthranilic acid (NP0087140)

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Record Information
Version2.0
Created at2022-05-11 16:41:14 UTC
Updated at2022-05-11 16:41:14 UTC
NP-MRD IDNP0087140
Secondary Accession NumbersNone
Natural Product Identification
Common NameFormylanthranilic acid
DescriptionFormylanthranilic acid, also known as N-formylanthranilate or 2-(formylamino)-benzoate, 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. Formylanthranilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). An amidobenzoic acid consisting of anthranilic acid carrying an N-formyl group. Formylanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, formylanthranilic acid participates in a number of enzymatic reactions. In particular, formylanthranilic acid and L-alanine can be biosynthesized from n'-formylkynurenine through its interaction with the enzyme kynureninase. In addition, formylanthranilic acid can be converted into 2-aminobenzoic acid and formic acid; which is mediated by the enzyme kynurenine formamidase. Formylanthranilic acid is found in Isatis tinctoria. Formylanthranilic acid was first documented in 1981 (PMID: 7320161). In humans, formylanthranilic acid is involved in tryptophan metabolism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087140 (Formylanthranilic acid)


  Mrv0541 02231219522D          

 12 12  0  0  0  0            999 V2000
   14.5859  -12.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1581  -11.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7292  -11.5824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3004  -12.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4437  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0148  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3004  -11.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0148  -10.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5859  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3004   -9.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5859  -10.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0148  -12.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
 12  4  1  0  0  0  0
M  END
Download

3D MOL for NP0087140 (Formylanthranilic acid)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    1.6212   -2.5748   -1.2990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -1.4284   -1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4148   -0.2965   -0.8914 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -0.3394   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332   -1.4688   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8694   -1.5144    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -0.3706    1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5150    0.7533    1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    0.8169    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    2.0495    0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    3.0489    1.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7519    2.3220    0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366   -1.2982   -1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8867    0.6490   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -2.3663   -0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -2.3958    0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -0.3800    1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8504    1.6620    1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618    3.1316   -0.4124 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
  4  9  1  0
 12 19  1  0
  8 18  1  0
  7 17  1  0
  6 16  1  0
  5 15  1  0
  3 14  1  0
  2 13  1  0
M  END
Download

3D SDF for NP0087140 (Formylanthranilic acid)


  Mrv0541 02231219522D          

 12 12  0  0  0  0            999 V2000
   14.5859  -12.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1581  -11.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7292  -11.5824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3004  -12.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4437  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0148  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3004  -11.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0148  -10.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5859  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3004   -9.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5859  -10.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0148  -12.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
 12  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087140

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO3/c10-5-9-7-4-2-1-3-6(7)8(11)12/h1-5H,(H,9,10)(H,11,12)

> <INCHI_KEY>
LLLPDUXGHXIXIW-UHFFFAOYSA-N

> <FORMULA>
C8H7NO3

> <MOLECULAR_WEIGHT>
165.1461

> <EXACT_MASS>
165.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.478287361935156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-formamidobenzoic acid

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
1.4698403833333331

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.005557567731586

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.566281304176154

> <JCHEM_PKA_STRONGEST_BASIC>
-4.538389350624696

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
43.6867

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
formylanthranilic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087140 (Formylanthranilic acid)

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PDB for NP0087140 (Formylanthranilic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      27.227 -23.930   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      33.895 -21.620   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      31.228 -21.620   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      28.561 -23.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.562 -20.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.894 -20.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.561 -21.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.894 -19.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.227 -20.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.561 -18.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.227 -19.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      29.894 -23.930   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    5    6                                                       
CONECT    4    1    7   12                                                  
CONECT    5    2    3                                                       
CONECT    6    3    7    8                                                  
CONECT    7    4    6    9                                                  
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    4                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0087140 (Formylanthranilic acid)
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SMILES for NP0087140 (Formylanthranilic acid)
OC(=O)C1=CC=CC=C1NC=O
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INCHI for NP0087140 (Formylanthranilic acid)
InChI=1S/C8H7NO3/c10-5-9-7-4-2-1-3-6(7)8(11)12/h1-5H,(H,9,10)(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-(Formylamino)-benzoic acidChEBI
2-(Formylamino)benzoic acidChEBI
N-FormylanthranilateKegg
2-(Formylamino)-benzoateGenerator
2-(Formylamino)benzoateGenerator
N-Formylanthranilic acidGenerator
FormylanthranilateGenerator
2-FormamidobenzoateHMDB
2-Formamidobenzoic acidHMDB
Chemical FormulaC8H7NO3
Average Mass165.1461 Da
Monoisotopic Mass165.04259 Da
IUPAC Name2-formamidobenzoic acid
Traditional Nameformylanthranilic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=CC=C1NC=O
InChI Identifier
InChI=1S/C8H7NO3/c10-5-9-7-4-2-1-3-6(7)8(11)12/h1-5H,(H,9,10)(H,11,12)
InChI KeyLLLPDUXGHXIXIW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Isatis tinctoriaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentBenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.28ALOGPS
logP1.47ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.69 m³·mol⁻¹ChemAxon
Polarizability15.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004089  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023309  
KNApSAcK IDNot Available
Chemspider ID91624  
KEGG Compound IDC05653  
BioCyc IDNot Available
BiGG ID46205  
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101399  
PDB IDNot Available
ChEBI ID36575  
Good Scents IDNot Available
References
General References
  1. Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. doi: 10.1016/s0378-4347(00)86064-8. [PubMed:7320161  ]