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Showing NP-Card for 3-Hydroxyanthranilic acid (NP0000205)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:57:55 UTC
NP-MRD IDNP0000205
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyanthranilic acid
Description3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a drug. 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, 3-hydroxyanthranilic acid participates in a number of enzymatic reactions. In particular, 3-hydroxyanthranilic acid and L-alanine can be biosynthesized from L-3-hydroxykynurenine through the action of the enzyme kynureninase. In addition, 3-hydroxyanthranilic acid can be converted into cinnavalininate through the action of the enzyme catalase. 3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. In humans, 3-hydroxyanthranilic acid is involved in tryptophan metabolism. Outside of the human body, 3-hydroxyanthranilic acid has been detected, but not quantified in brassicas. This could make 3-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. It is new antioxidant isolated from methanol extract of tempeh. It is effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4'-trihydroxyisoflavone is not.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000205 (3-Hydroxyanthranilic acid)


  Mrv1652305261923572D          

 11 11  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 N   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
    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 O   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 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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for NP0000205 (3-Hydroxyanthranilic acid)

HMDB0001476
     RDKit          3D
3-Hydroxyanthranilic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    0.0966   -1.9052   -0.1084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560   -0.5249   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.1476   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933   -1.0847   -0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091    1.1990    0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    2.1153    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417    1.7495    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7559    0.4161    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613    0.0347    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739    0.8906    0.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604   -1.3175    0.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -2.4851    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368   -2.3623   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213   -2.0553   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543    1.4490    0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    3.1770    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015    2.5251    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -1.6737   -0.7314 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8  2  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0000205 (3-Hydroxyanthranilic acid)


  Mrv1652305261923572D          

 11 11  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 N   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
    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 O   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 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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000205

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)

> <INCHI_KEY>
WJXSWCUQABXPFS-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.1354

> <EXACT_MASS>
153.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.18473050411826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-hydroxybenzoic acid

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
1.148337448333333

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.367676493177447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9368311681755785

> <JCHEM_PKA_STRONGEST_BASIC>
4.81889092275183

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
39.9955

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyanthranilic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000205 (3-Hydroxyanthranilic acid)

HMDB0001476
     RDKit          3D
3-Hydroxyanthranilic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    0.0966   -1.9052   -0.1084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560   -0.5249   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.1476   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933   -1.0847   -0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091    1.1990    0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    2.1153    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417    1.7495    0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7559    0.4161    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613    0.0347    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739    0.8906    0.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604   -1.3175    0.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -2.4851    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368   -2.3623   -1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213   -2.0553   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9543    1.4490    0.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567    3.1770    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015    2.5251    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -1.6737   -0.7314 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8  2  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
 11 18  1  0
M  END
Download

PDB for NP0000205 (3-Hydroxyanthranilic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   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   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000205 (3-Hydroxyanthranilic acid)

COMPND    HMDB0001476
HETATM    1  N1  UNL     1       0.097  -1.905  -0.108  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.256  -0.525  -0.012  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.582  -0.148  -0.039  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.593  -1.085  -0.158  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.909   1.199   0.055  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.885   2.115   0.173  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.442   1.750   0.201  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.756   0.416   0.107  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.161   0.035   0.136  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.074   0.891   0.244  1.00  0.00           O  
HETATM   11  O3  UNL     1       2.460  -1.317   0.040  1.00  0.00           O  
HETATM   12  H1  UNL     1       0.117  -2.485   0.756  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.337  -2.362  -1.013  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.321  -2.055  -0.224  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.954   1.449   0.031  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.157   3.177   0.247  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.201   2.525   0.296  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.014  -1.674  -0.731  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   14
CONECT    5    6    6   15
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   18
END
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SMILES for NP0000205 (3-Hydroxyanthranilic acid)

NC1=C(O)C=CC=C1C(O)=O
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INCHI for NP0000205 (3-Hydroxyanthranilic acid)

InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2-Amino-3-hydroxy-benzoic acidChEBI
2-Amino-3-hydroxybenzoic acidChEBI
3-OhaaChEBI
3-Oxyanthranilic acidChEBI
2-Amino-3-hydroxy-benzoateGenerator
2-Amino-3-hydroxybenzoateGenerator
3-OxyanthranilateGenerator
3-HydroxyanthranilateGenerator
3-HydroxanthranilateHMDB
3-Hydroxy-2-aminobenzoateHMDB
3-Hydroxy-2-aminobenzoic acidHMDB
3-Hydroxy-anthranilateHMDB
3-Hydroxy-anthranilic acidHMDB
3-Hydroxy-anthranilsaeureHMDB
3-Hydroxyantranilic acidHMDB
3-OH-Anthranilic acidHMDB
3 Hydroxyanthranilic acidHMDB
Acid, 3-hydroxyanthranilicHMDB
Chemical FormulaC7H7NO3
Average Mass153.1354 Da
Monoisotopic Mass153.04259 Da
IUPAC Name2-amino-3-hydroxybenzoic acid
Traditional Name3-hydroxyanthranilic acid
CAS Registry Number548-93-6
SMILES
NC1=C(O)C=CC=C1C(O)=O
InChI Identifier
InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
InChI KeyWJXSWCUQABXPFS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
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
Brassica oleraceaKNApSAcK Database
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
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
Species Where Detected
Species NameSourceReference
Arthrobacter protophormiaeKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-aminophenol
  • Aminophenol
  • Benzoyl
  • Aniline or substituted anilines
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12970 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.81ALOGPS
logP1.15ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001476
DrugBank IDDB03644
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010582
KNApSAcK IDC00007568
Chemspider ID84
KEGG Compound IDC00632
BioCyc ID3-HYDROXY-ANTHRANILATE
BiGG ID1485273
Wikipedia Link3-hydroxyanthranilic_acid
METLIN ID3275
PubChem Compound86
PDB IDNot Available
ChEBI ID15793
Good Scents IDrw1190601
References
General References
  1. De Antoni A, Rubaltelli FF, Costa C, Allegri G: Effect of phototherapy on the urinary excretion of tryptophan metabolites in neonatal hyperbilirubinemia. Acta Vitaminol Enzymol. 1975;29(1-6):145-50. [PubMed:1244083 ]
  2. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
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