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Showing NP-Card for 5-[amino(carboxy)methyl]-2-hydroxybenzoic acid (NP0156543)

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Record Information
Version2.0
Created at2022-09-02 13:46:00 UTC
Updated at2022-09-02 13:46:00 UTC
NP-MRD IDNP0156543
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-[amino(carboxy)methyl]-2-hydroxybenzoic acid
Description5-[Amino(carboxy)methyl]-2-hydroxybenzoic acid belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 5-[amino(carboxy)methyl]-2-hydroxybenzoic acid is found in Caylusea abyssinica and Reseda luteola. 5-[Amino(carboxy)methyl]-2-hydroxybenzoic acid is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)


  Mrv1533004241523542D          

 15 15  0  0  0  0            999 V2000
    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
    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 N   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
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
M  END
Download

3D MOL for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    0.3005   -1.0336    2.9453 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    0.1090    2.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0165    0.2858    1.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020   -0.5520    2.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6650    1.3139    1.3084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -0.0282    0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -0.4013    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.5511   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5892   -0.3134   -1.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3048   -0.4532   -2.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588    0.0623   -1.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3363    0.2957   -2.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109    0.1681   -3.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6612    0.6703   -2.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724    0.2069   -0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5787   -1.8808    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -1.0825    3.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1308    0.9917    2.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306    2.2781    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9923   -0.5952    1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750   -0.8490   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593   -0.7216   -2.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267    1.5806   -2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.4994   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6 15  2  0
 15 11  1  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  5 19  1  0
 15 24  1  0
 14 23  1  0
 10 22  1  0
  8 21  1  0
  7 20  1  0
M  END
Download

3D SDF for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)


  Mrv1533004241523542D          

 15 15  0  0  0  0            999 V2000
    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
    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 N   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
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156543

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO5/c10-7(9(14)15)4-1-2-6(11)5(3-4)8(12)13/h1-3,7,11H,10H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
CHZBCZTXSTWCIG-UHFFFAOYSA-N

> <FORMULA>
C9H9NO5

> <MOLECULAR_WEIGHT>
211.173

> <EXACT_MASS>
211.048072394

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.18428759302795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[amino(carboxy)methyl]-2-hydroxybenzoic acid

> <ALOGPS_LOGP>
-2.67

> <JCHEM_LOGP>
-1.554636487705864

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.9377768067677303

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1086124250995377

> <JCHEM_PKA_STRONGEST_BASIC>
8.642601258512007

> <JCHEM_POLAR_SURFACE_AREA>
120.85

> <JCHEM_REFRACTIVITY>
49.5984

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[amino(carboxy)methyl]-2-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)

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PDB for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   1.540   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       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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.000   4.620   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)
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SMILES for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)
NC(C(O)=O)C1=CC(C(O)=O)=C(O)C=C1
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INCHI for NP0156543 (5-[amino(carboxy)methyl]-2-hydroxybenzoic acid)
InChI=1S/C9H9NO5/c10-7(9(14)15)4-1-2-6(11)5(3-4)8(12)13/h1-3,7,11H,10H2,(H,12,13)(H,14,15)
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View in JSmol
Synonyms
ValueSource
5-[Amino(carboxy)methyl]-2-hydroxybenzoateGenerator
Chemical FormulaC9H9NO5
Average Mass211.1730 Da
Monoisotopic Mass211.04807 Da
IUPAC Name5-[amino(carboxy)methyl]-2-hydroxybenzoic acid
Traditional Name5-[amino(carboxy)methyl]-2-hydroxybenzoic acid
CAS Registry NumberNot Available
SMILES
NC(C(O)=O)C1=CC(C(O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H9NO5/c10-7(9(14)15)4-1-2-6(11)5(3-4)8(12)13/h1-3,7,11H,10H2,(H,12,13)(H,14,15)
InChI KeyCHZBCZTXSTWCIG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Caylusea abyssinicaLOTUS Database
Reseda luteolaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentSalicylic acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Salicylic acid
    • 

  • Benzoic acid
    • 

  • Benzoyl
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Aralkylamine
    • 

  • Phenol
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Vinylogous acid
    • 

  • Amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Aromatic homomonocyclic compound
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-2.7ALOGPS
logP-1.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.11ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.6 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4014619  
PDB IDNot Available
ChEBI ID93840  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]