NP-MRD: Showing NP-Card for 3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium (NP0178124)

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Record Information

Version

2.0

Created at

2022-09-03 16:03:49 UTC

Updated at

2022-09-03 16:03:49 UTC

NP-MRD ID

NP0178124

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium

Description

3-[(4-Carboxylato-2,6-dihydroxyphenoxy)carbonyl]-1-methylpyridin-1-ium belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. 3-[(4-Carboxylato-2,6-dihydroxyphenoxy)carbonyl]-1-methylpyridin-1-ium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    5.2236   -0.5260   -1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1869   -0.2406   -0.3755 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.5750    0.0530    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6136    0.3365    1.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852    0.3057    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486   -0.0003    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -0.0330   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -0.3071   -1.3825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737    0.2361    0.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106    0.2044    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971    1.3013   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    2.4901   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    1.2647   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271    0.0698   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9180    0.0241   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4891    1.0524   -1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5901   -1.1831   -0.6960 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.8601   -1.0438    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -0.9679    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163   -2.1167    0.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9110   -0.2770   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088    0.0839   -2.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2299   -0.2648   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1182   -1.5900   -1.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6054    0.0828    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831    0.5746    2.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5537    0.5285    2.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2163    3.3434   -0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621    2.1196   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748   -2.0036    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -2.9962    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -0.5206   -1.7851 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 21  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 21  2  1  0
 19 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
 21 32  1  0
 12 28  1  0
 13 29  1  0
 18 30  1  0
 20 31  1  0
M  CHG  2   2   1  17  -1
M  END


  Mrv1533004241517442D          

 21 22  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  3  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
    0.7145   -3.7125    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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 O   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
   -2.1434   -6.1875    0.0000 C   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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  5  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  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  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
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  CHG  2   2   1  21  -1
M  END
> <DATABASE_ID>
NP0178124

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+]1=CC=CC(=C1)C(=O)OC1=C(O)C=C(C=C1O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO6/c1-15-4-2-3-8(7-15)14(20)21-12-10(16)5-9(13(18)19)6-11(12)17/h2-7H,1H3,(H2-,16,17,18,19)

> <INCHI_KEY>
KIDWQBQBVJXTPW-UHFFFAOYSA-N

> <FORMULA>
C14H11NO6

> <MOLECULAR_WEIGHT>
289.243

> <EXACT_MASS>
289.058637078

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.54430361040562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-carboxylato-2,6-dihydroxyphenoxy)carbonyl]-1-methylpyridin-1-ium

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-1.1759072934717452

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.015810598988585

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8038692387771187

> <JCHEM_PKA_STRONGEST_BASIC>
-4.107302584472721

> <JCHEM_POLAR_SURFACE_AREA>
110.77000000000001

> <JCHEM_REFRACTIVITY>
83.9145

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium

> <JCHEM_VEBER_RULE>
0

$$$$

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  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O-1
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   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₁NO₆

Average Mass

289.2430 Da

Monoisotopic Mass

289.05864 Da

IUPAC Name

3-[(4-carboxylato-2,6-dihydroxyphenoxy)carbonyl]-1-methylpyridin-1-ium

Traditional Name

3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium

CAS Registry Number

Not Available

SMILES

C[N+]1=CC=CC(=C1)C(=O)OC1=C(O)C=C(C=C1O)C([O-])=O

InChI Identifier

InChI=1S/C14H11NO6/c1-15-4-2-3-8(7-15)14(20)21-12-10(16)5-9(13(18)19)6-11(12)17/h2-7H,1H3,(H2-,16,17,18,19)

InChI Key

KIDWQBQBVJXTPW-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
Phenol ester
Benzoic acid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Phenoxy compound
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
N-methylpyridinium
Phenol
Phenoxide
Pyridine
Pyridinium
Heteroaromatic compound
Vinylogous amide
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-1.2	ALOGPS
logP	-1.2	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.91 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium (NP0178124)

MOL for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

3D MOL for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

3D SDF for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

3D-SDF for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

PDB for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

3D PDB for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

SMILES for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

INCHI for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

Structure for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)

3D Structure for NP0178124 (3-(4-carboxylato-2,6-dihydroxyphenoxycarbonyl)-1-methylpyridin-1-ium)