NP-MRD: Showing NP-Card for 2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid (NP0228053)

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Record Information

Version

2.0

Created at

2022-09-06 07:34:07 UTC

Updated at

2022-09-06 07:34:08 UTC

NP-MRD ID

NP0228053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid

Description

2,5-Dihydroxy-N-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzene-1-carboximidic acid 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. 2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid is found in Aconitum barbatum. 2,5-Dihydroxy-N-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzene-1-carboximidic acid 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
    7.0812   -0.3884    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6610   -0.3125    0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9049   -0.2305   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141   -0.2264   -1.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419   -0.1510   -0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7551   -0.1538    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3525   -0.0776    0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    0.0026   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8002    0.0830   -0.3362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6703    0.0949    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    0.0270    1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1075    0.1766    0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8540    0.1766    1.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2207    0.2531    1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858    0.2550    3.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8934    0.3320    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025    0.3345   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    0.2554   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1915    0.2653   -1.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511    0.0037   -1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    0.0848   -2.6735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7224   -0.0711   -1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5501    0.5872    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3884   -0.5788   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4812   -1.1693    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -0.2179    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296   -0.0884    1.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.1399   -1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3281    0.1149    2.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2795   -0.6498    3.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9594    0.3910    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7394    0.3968   -1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    0.3216   -2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320    0.0868   -3.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -0.0672   -2.4883 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  1  0
 20 21  1  0
 20 22  2  0
 22  5  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 21 34  1  0
 22 35  1  0
M  END


  Mrv1533004231520232D          

 22 23  0  0  0  0            999 V2000
    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.1434   -2.8875    0.0000 C   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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   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
    0.0000   -4.1250    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  5 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228053

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
QKJXTDDURNMKEZ-UHFFFAOYSA-N

> <FORMULA>
C15H13NO6

> <MOLECULAR_WEIGHT>
303.27

> <EXACT_MASS>
303.074287143

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.779657099959284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-(2,5-dihydroxybenzamido)-3-hydroxybenzoate

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.1579116206666664

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.672834010988437

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.066675566084802

> <JCHEM_PKA_STRONGEST_BASIC>
-4.451233436816892

> <JCHEM_POLAR_SURFACE_AREA>
116.09

> <JCHEM_REFRACTIVITY>
79.5595

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-(2,5-dihydroxybenzamido)-3-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20    8   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
2,5-Dihydroxy-N-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzene-1-carboximidate	Generator

Chemical Formula

C₁₅H₁₃NO₆

Average Mass

303.2700 Da

Monoisotopic Mass

303.07429 Da

IUPAC Name

methyl 4-(2,5-dihydroxybenzamido)-3-hydroxybenzoate

Traditional Name

methyl 4-(2,5-dihydroxybenzamido)-3-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

QKJXTDDURNMKEZ-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
Aconitum barbatum	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
M-hydroxybenzoic acid ester
Salicylamide
Salicylic acid or derivatives
Benzoate ester
Benzamide
Benzoic acid or derivatives
Hydroquinone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Vinylogous acid
Methyl ester
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organonitrogen 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	2.24	ALOGPS
logP	2.16	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.56 m³·mol⁻¹	ChemAxon
Polarizability	28.78 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

101472880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid (NP0228053)

MOL for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

3D MOL for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

3D SDF for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

3D-SDF for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

PDB for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

3D PDB for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

SMILES for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

INCHI for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

Structure for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)

3D Structure for NP0228053 (2,5-dihydroxy-n-[2-hydroxy-4-(methoxycarbonyl)phenyl]benzenecarboximidic acid)