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Showing NP-Card for Orthanilic acid (NP0002904)

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Record Information
Version2.0
Created at2020-11-23 19:43:16 UTC
Updated at2021-08-12 19:52:28 UTC
NP-MRD IDNP0002904
Secondary Accession NumbersNone
Natural Product Identification
Common NameOrthanilic acid
Provided ByBMRBBMRB logo
Description2-Aminobenzenesulfonic acid, also known as O-aminobenzenesulphonate or aniline-O-sulfonic acid, belongs to the class of organic compounds known as benzenesulfonic acids and derivatives. These are organic compounds containing a sulfonic acid or a derivative thereof that is linked to a benzene ring. 2-Aminobenzenesulfonic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Orthanilic acid was first documented in 2011 (PMID: 20638913). Based on a literature review a small amount of articles have been published on 2-Aminobenzenesulfonic acid (PMID: 23392615) (PMID: 33676646).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002904 (Orthanilic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    0.2719   -2.3309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927   -0.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603    0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2337    1.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4339    0.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    0.1686    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.8374   -1.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244    1.6657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4280    0.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690   -2.4244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5576   -3.5806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -2.1439    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574    0.5426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984    3.0422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    2.8552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.3249    0.0000 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  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  1
  7  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
 11 18  1  0
M  END
Download

3D MOL for NP0002904 (Orthanilic acid)

NP0002904
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    0.3669    1.9667    0.3990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289    0.7694    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6709    0.7222    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527   -0.4605    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7373   -1.5723   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919   -1.4729   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237   -0.3106   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170   -0.1651   -0.7636 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.5703   -1.4419   -1.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2422    0.9861   -1.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8894    0.2220    0.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0576    2.8791    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145    1.9584    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    1.5892    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966   -0.4832    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916   -2.4853   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277   -2.3129   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -0.3886    1.3589 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  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  7  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0002904 (Orthanilic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    0.2719   -2.3309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927   -0.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603    0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2337    1.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4339    0.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    0.1686    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.8374   -1.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244    1.6657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4280    0.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690   -2.4244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5576   -3.5806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -2.1439    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574    0.5426    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984    3.0422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    2.8552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.3249    0.0000 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  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  1
  7  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
 11 18  1  0
M  END
> <DATABASE_ID>
NP0002904

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=CC=C1S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10)

> <INCHI_KEY>
ZMCHBSMFKQYNKA-UHFFFAOYSA-N

> <FORMULA>
C6H7NO3S

> <MOLECULAR_WEIGHT>
173.19

> <EXACT_MASS>
173.014664263

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.486244199390521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminobenzene-1-sulfonic acid

> <ALOGPS_LOGP>
-1.51

> <JCHEM_LOGP>
0.10179620433501496

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.888873346320146

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.721514011875187

> <JCHEM_PKA_STRONGEST_BASIC>
2.3279385165553133

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
41.380900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orthanilic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002904 (Orthanilic acid)

NP0002904
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    0.3669    1.9667    0.3990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289    0.7694    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6709    0.7222    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527   -0.4605    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7373   -1.5723   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919   -1.4729   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237   -0.3106   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170   -0.1651   -0.7636 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.5703   -1.4419   -1.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2422    0.9861   -1.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8894    0.2220    0.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0576    2.8791    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145    1.9584    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1793    1.5892    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966   -0.4832    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916   -2.4853   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277   -2.3129   -0.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -0.3886    1.3589 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  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  7  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
 11 18  1  0
M  END
Download

PDB for NP0002904 (Orthanilic acid)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.206   3.850   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5   11                                                  
CONECT    7    5                                                            
CONECT    8   11                                                            
CONECT    9   11                                                            
CONECT   10   11                                                            
CONECT   11    6    8    9   10                                             
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002904 (Orthanilic acid)

COMPND    NP0002904
HETATM    1  N1  UNL     1       0.367   1.967   0.399  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.329   0.769   0.197  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.671   0.722   0.555  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.353  -0.460   0.355  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.737  -1.572  -0.184  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.392  -1.473  -0.525  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.324  -0.311  -0.341  1.00  0.00           C  
HETATM    8  S1  UNL     1       2.017  -0.165  -0.764  1.00  0.00           S  
HETATM    9  O1  UNL     1       2.570  -1.442  -1.276  1.00  0.00           O  
HETATM   10  O2  UNL     1       2.242   0.986  -1.712  1.00  0.00           O  
HETATM   11  O3  UNL     1       2.889   0.222   0.645  1.00  0.00           O  
HETATM   12  H1  UNL     1      -0.058   2.879   0.144  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.314   1.958   0.806  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.179   1.589   0.983  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.397  -0.483   0.637  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.292  -2.485  -0.331  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.128  -2.313  -0.947  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.555  -0.389   1.359  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3    7
CONECT    3    4   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   18
END
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SMILES for NP0002904 (Orthanilic acid)

NC1=CC=CC=C1S(O)(=O)=O
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INCHI for NP0002904 (Orthanilic acid)

InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
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View in JSmol
Synonyms
ValueSource
1-Aminobenzene-2-sulfonic acidChEBI
2-Sulfanilic acidChEBI
Aniline-O-sulfonic acidChEBI
Aniline-O-sulphonic acidChEBI
O-Aminobenzenesulfonic acidChEBI
O-Sulfanilic acidChEBI
Orthanilic acidChEBI
1-Aminobenzene-2-sulfonateGenerator
1-Aminobenzene-2-sulphonateGenerator
1-Aminobenzene-2-sulphonic acidGenerator
2-SulfanilateGenerator
2-SulphanilateGenerator
2-Sulphanilic acidGenerator
Aniline-O-sulfonateGenerator
Aniline-O-sulphonateGenerator
O-AminobenzenesulfonateGenerator
O-AminobenzenesulphonateGenerator
O-Aminobenzenesulphonic acidGenerator
O-SulfanilateGenerator
O-SulphanilateGenerator
O-Sulphanilic acidGenerator
OrthanilateGenerator
2-AminobenzenesulfonateGenerator
2-AminobenzenesulphonateGenerator
2-Aminobenzenesulphonic acidGenerator
Ortho-sulfanilic acidHMDB
Chemical FormulaC6H7NO3S
Average Mass173.1900 Da
Monoisotopic Mass173.01466 Da
IUPAC Name2-aminobenzene-1-sulfonic acid
Traditional Nameorthanilic acid
CAS Registry NumberNot Available
SMILES
NC1=CC=CC=C1S(O)(=O)=O
InChI Identifier
InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
InChI KeyZMCHBSMFKQYNKA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonic acids and derivatives. These are organic compounds containing a sulfonic acid or a derivative thereof that is linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonic acids and derivatives
Direct ParentBenzenesulfonic acids and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP-1.5ALOGPS
logP0.1ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-3.7ChemAxon
pKa (Strongest Basic)2.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.38 m³·mol⁻¹ChemAxon
Polarizability15.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0304940
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6660
KEGG Compound IDC06333
BioCyc ID2-AMINOBENZENESULFONATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6926
PDB IDNot Available
ChEBI ID1015
Good Scents IDNot Available
References
General References
  1. Sanchis C, Ghanem MA, Salavagione HJ, Morallon E, Bartlett PN: The oxidation of ascorbate at copolymeric sulfonated poly(aniline) coated on glassy carbon electrodes. Bioelectrochemistry. 2011 Feb;80(2):105-13. doi: 10.1016/j.bioelechem.2010.06.006. Epub 2010 Jul 1. [PubMed:20638913 ]
  2. Kale SS, Priya G, Kotmale AS, Gawade RL, Puranik VG, Rajamohanan PR, Sanjayan GJ: Orthanilic acid-promoted reverse turn formation in peptides. Chem Commun (Camb). 2013 Mar 18;49(22):2222-4. doi: 10.1039/c3cc40522b. [PubMed:23392615 ]
  3. Wu F, Gu L, Dai X, Yang S, Xu F, Fang X, Yu S, Ding CF: Direct and simultaneous recognition of the positional isomers of aminobenzenesulfonic acid by TIMS-TOF-MS. Talanta. 2021 May 1;226:122085. doi: 10.1016/j.talanta.2021.122085. Epub 2021 Jan 7. [PubMed:33676646 ]