NP-MRD: Showing NP-Card for 2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid (NP0234979)

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Record Information

Version

2.0

Created at

2022-09-06 17:21:01 UTC

Updated at

2022-09-06 17:21:01 UTC

NP-MRD ID

NP0234979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid

Description

115610-39-4 Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. 2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid is found in Dianthus caryophyllus. 115610-39-4 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    4.1207   -2.1569   -1.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355   -0.9455   -0.9276 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857    0.0096   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    1.1787    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    2.1401    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9633    1.9914    0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    3.0295    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015    4.0668    1.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1639    3.0502    1.5103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508    0.8187    0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0590    0.6219    0.1510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -0.5505   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0196   -1.5805   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226   -0.6487   -0.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658    0.4700    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2658    0.4905    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441   -0.6647   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533   -0.6998   -0.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2278   -1.7840   -0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8099   -1.8026   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -2.9625   -0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -0.1487   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930   -2.8889   -0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027   -2.5933   -2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1692   -2.1051   -2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2574    1.3150    0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7785    3.0633    1.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480    2.9499    2.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    1.4535    0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930    1.4060    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8222    1.3905    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8122   -0.9356    0.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7309   -2.7172   -0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2526   -3.1874   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -1.0735   -0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 10 22  2  0
 22  3  1  0
 20 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 22 35  1  0
M  END


  Mrv1533004161508232D          

 22 23  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 22  2  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C(O)=O)C(NC(=O)C2=CC=C(O)C=C2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO6/c1-22-9-3-5-10(15(20)21)12(7-9)16-14(19)11-4-2-8(17)6-13(11)18/h2-7,17-18H,1H3,(H,16,19)(H,20,21)

> <INCHI_KEY>
GLXWWDVTVBGZGZ-UHFFFAOYSA-N

> <FORMULA>
C15H13NO6

> <MOLECULAR_WEIGHT>
303.27

> <EXACT_MASS>
303.074287143

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.66863105205752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dihydroxybenzamido)-4-methoxybenzoic acid

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.607911620666666

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.847260175400385

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8522411274862156

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158743955718526

> <JCHEM_POLAR_SURFACE_AREA>
116.09

> <JCHEM_REFRACTIVITY>
79.27270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2,4-dihydroxybenzamido)-4-methoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   10    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃NO₆

Average Mass

303.2700 Da

Monoisotopic Mass

303.07429 Da

IUPAC Name

2-(2,4-dihydroxybenzamido)-4-methoxybenzoic acid

Traditional Name

2-(2,4-dihydroxybenzamido)-4-methoxybenzoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(O)=O)C(NC(=O)C2=CC=C(O)C=C2O)=C1

InChI Identifier

InChI=1S/C15H13NO6/c1-22-9-3-5-10(15(20)21)12(7-9)16-14(19)11-4-2-8(17)6-13(11)18/h2-7,17-18H,1H3,(H,16,19)(H,20,21)

InChI Key

GLXWWDVTVBGZGZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dianthus caryophyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
P-methoxybenzoic acid or derivatives
Salicylamide
Salicylic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoic acid
Methoxyaniline
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Resorcinol
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Vinylogous amide
Vinylogous acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.64	ALOGPS
logP	2.61	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.27 m³·mol⁻¹	ChemAxon
Polarizability	28.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid (NP0234979)

MOL for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

3D MOL for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

3D SDF for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

3D-SDF for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

PDB for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

3D PDB for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

SMILES for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

INCHI for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

Structure for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)

3D Structure for NP0234979 (2-{[(2,4-dihydroxyphenyl)(hydroxy)methylidene]amino}-4-methoxybenzoic acid)