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Showing NP-Card for 2,3-dihydroxybenzamide (NP0331202)

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Record Information
Version2.0
Created at2022-12-13 17:51:16 UTC
Updated at2024-09-03 04:14:53 UTC
NP-MRD IDNP0331202
Natural Product DOIhttps://doi.org/10.57994/0073
Secondary Accession Numbers
  • NP0219058
Natural Product Identification
Common Name2,3-dihydroxybenzamide
DescriptionTrencam-3,2-Hopo belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid. Trencam-3,2-Hopo is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331202 (2,3-dihydroxybenzamide)


  Mrv0541 02231217422D          

 11 11  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    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 O   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 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
  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0331202 (2,3-dihydroxybenzamide)

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3D SDF for NP0331202 (2,3-dihydroxybenzamide)

  Mrv0541 02231217422D          

 11 11  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    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 O   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 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
  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=CC=CC(O)=C1O

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

> <INCHI_KEY>
QCIDBNKTKNBPKM-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.1354

> <EXACT_MASS>
153.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.135277634098443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxybenzamide

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
0.8667554669999998

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.927945844024205

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.32455798536269

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8588129294971703

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
39.0982

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trencam-3,2-hopo

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0331202 (2,3-dihydroxybenzamide)
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PDB for NP0331202 (2,3-dihydroxybenzamide)
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  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0331202 (2,3-dihydroxybenzamide)
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SMILES for NP0331202 (2,3-dihydroxybenzamide)
NC(=O)C1=CC=CC(O)=C1O
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INCHI for NP0331202 (2,3-dihydroxybenzamide)
InChI=1S/C7H7NO3/c8-7(11)4-2-1-3-5(9)6(4)10/h1-3,9-10H,(H2,8,11)
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View in JSmol
Synonyms
ValueSource
2,3-Dihydroxybenzene-1-carboximidateGenerator
Chemical FormulaC7H7NO3
Average Mass153.1354 Da
Monoisotopic Mass153.04259 Da
IUPAC Name2,3-dihydroxybenzamide
Traditional Nametrencam-3,2-hopo
CAS Registry NumberNot Available
SMILES
NC(=O)C1=CC=CC(O)=C1O
InChI Identifier
InChI=1S/C7H7NO3/c8-7(11)4-2-1-3-5(9)6(4)10/h1-3,9-10H,(H2,8,11)
InChI KeyQCIDBNKTKNBPKM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)ravishankar@niist.res.inNot AvailableNot Available2022-12-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)ravishankar@niist.res.inNot AvailableNot Available2022-12-13View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentSalicylamides  
Alternative Parents
Substituents
  • Salicylamide
    • 

  • Benzamide
    • 

  • Benzoyl
    • 

  • Catechol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • Carboxamide group
    • 

  • Primary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0.42ALOGPS
logP0.87ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.32ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.1 m³·mol⁻¹ChemAxon
Polarizability14.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04476  
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 Compound449146  
PDB IDDB1  
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. DOI: 10.1038/s41429-022-00547-1
  2. PMID: 35922482