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Showing NP-Card for m-Aminobenzoic acid (NP0001362)

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Record Information
Version1.0
Created at2006-03-07 16:38:32 UTC
Updated at2021-10-07 20:42:16 UTC
NP-MRD IDNP0001362
Secondary Accession NumbersNone
Natural Product Identification
Common Namem-Aminobenzoic acid
DescriptionM-Aminobenzoic acid (also known as 3-aminobenzoic acid or MABA) is an organic compound with the molecular formula H2NC6H4CO2H. MABA is a white solid, although commercial samples are often colored. It is only slightly soluble in water. It is soluble in acetone, boiling water, hot alcohol, hot chloroform and ether. It consists of a benzene ring substituted with an amino group and a carboxylic acid. M-Aminobenzoic acid belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Outside of the human body, m-Aminobenzoic acid has been detected, but not quantified in cow milk. This could make m-aminobenzoic acid a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001362 (m-Aminobenzoic acid)


  Mrv1652305271900192D          

 10 10  0  0  0  0            999 V2000
    2.1434   -0.4125    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
    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
    1.4289    0.8250    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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
Download

3D MOL for NP0001362 (m-Aminobenzoic acid)

HMDB0001891
     RDKit          3D
m-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.6537   -0.4847   -0.9832 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -0.1771   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882    0.3747    0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226    0.6862    1.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    0.4170    1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -0.1301   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -0.3976   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -0.8903   -1.9447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.0943   -0.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006   -0.4250   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599   -1.4390   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1581    0.2098   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4413    0.5742    1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146    1.1178    2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    0.6464    1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877    0.8661    0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1878   -0.8540   -1.8456 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  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

3D SDF for NP0001362 (m-Aminobenzoic acid)


  Mrv1652305271900192D          

 10 10  0  0  0  0            999 V2000
    2.1434   -0.4125    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
    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
    1.4289    0.8250    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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001362

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10)

> <INCHI_KEY>
XFDUHJPVQKIXHO-UHFFFAOYSA-N

> <FORMULA>
C7H7NO2

> <MOLECULAR_WEIGHT>
137.136

> <EXACT_MASS>
137.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.405718816946653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-aminobenzoic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.6308152429896937

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.810833625289855

> <JCHEM_PKA_STRONGEST_BASIC>
3.2715362421122087

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
38.0146

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gabaculine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001362 (m-Aminobenzoic acid)

HMDB0001891
     RDKit          3D
m-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.6537   -0.4847   -0.9832 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -0.1771   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882    0.3747    0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226    0.6862    1.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    0.4170    1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -0.1301   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -0.3976   -0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -0.8903   -1.9447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.0943   -0.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006   -0.4250   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599   -1.4390   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1581    0.2098   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4413    0.5742    1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146    1.1178    2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    0.6464    1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877    0.8661    0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1878   -0.8540   -1.8456 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  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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PDB for NP0001362 (m-Aminobenzoic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0001362 (m-Aminobenzoic acid)

COMPND    HMDB0001891
HETATM    1  N1  UNL     1       2.654  -0.485  -0.983  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.444  -0.177  -0.285  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.488   0.375   0.981  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.323   0.686   1.688  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.861   0.417   1.063  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.970  -0.130  -0.192  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.267  -0.398  -0.814  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.375  -0.890  -1.945  1.00  0.00           O  
HETATM    9  O2  UNL     1      -3.432  -0.094  -0.126  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.201  -0.425  -0.861  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.060  -1.439  -0.923  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.158   0.210  -1.559  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.441   0.574   1.444  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.415   1.118   2.678  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.778   0.646   1.584  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.688   0.866   0.096  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.188  -0.854  -1.846  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    3   10
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7   10   10
CONECT    7    8    8    9
CONECT    9   16
CONECT   10   17
END
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SMILES for NP0001362 (m-Aminobenzoic acid)

NC1=CC=CC(=C1)C(O)=O
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INCHI for NP0001362 (m-Aminobenzoic acid)

InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10)
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View in JSmol
Synonyms
ValueSource
3-AminobenzoesaeureChEBI
3-CarboxyanilineChEBI
m-AminobenzoesaeureChEBI
m-CarboxyanilineChEBI
MABAChEBI
m-AminobenzoateGenerator
Meta-aminobenzoic acidHMDB
3-Aminobenzoic acid, monosodium saltHMDB
Aniline-3-carboxylateHMDB
3-AminobenzoateHMDB
3-Aminobenzoic acidHMDB
Aniline-3-carboxylic acidHMDB
m-AmonibenzoateHMDB
m-Amonibenzoic acidHMDB
m-Aminobenzoic acidChEBI
Chemical FormulaC7H7NO2
Average Mass137.1360 Da
Monoisotopic Mass137.04768 Da
IUPAC Name3-aminobenzoic acid
Traditional Namegabaculine
CAS Registry Number99-05-8
SMILES
NC1=CC=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyXFDUHJPVQKIXHO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 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
Bos taurusMilk
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point173 °CNot Available
Boiling Point352.55 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5.9 mg/mL at 15 °CNot Available
LogP0.65Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility6.36 g/LALOGPS
logP0.93ALOGPS
logP0.63ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.81ChemAxon
pKa (Strongest Basic)3.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001891
DrugBank IDDB02054
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022725
KNApSAcK IDNot Available
Chemspider ID7141
KEGG Compound IDNot Available
BioCyc IDHMDB01891
BiGG IDNot Available
Wikipedia Link3-Aminobenzoic_acid
METLIN ID6374
PubChem Compound7419
PDB IDNot Available
ChEBI ID42682
Good Scents IDrw1187341
References
General References
  1. Wachsman JT: The beneficial effects of dietary restriction: reduced oxidative damage and enhanced apoptosis. Mutat Res. 1996 Feb 19;350(1):25-34. [PubMed:8657188 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  4. Buchanan CM, Peng Z, Cefre A, Sarojini V: Preptin analogues: chemical synthesis, secondary structure and biological studies. Chem Biol Drug Des. 2013 Oct;82(4):429-37. doi: 10.1111/cbdd.12168. [PubMed:23745966 ]
  5. Benke BP, Madhavan N: Active ion transporters from readily accessible acyclic octapeptides containing 3-aminobenzoic acid and alanine. Chem Commun (Camb). 2013 Aug 25;49(66):7340-2. doi: 10.1039/c3cc44224a. [PubMed:23851602 ]