NP-MRD: Showing NP-Card for Phenopicolinic acid (NP0003807)

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Record Information

Version

2.0

Created at

2020-12-09 00:57:16 UTC

Updated at

2021-07-15 16:47:26 UTC

NP-MRD ID

NP0003807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenopicolinic acid

Provided By

NPAtlas

Description

Phenopicolinic acid is found in Paecilomyces. Phenopicolinic acid was first documented in 1975 (PMID: 1150540). Based on a literature review very few articles have been published on 5-[(4-hydroxyphenyl)methyl]pyridine-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117503D          

 28 29  0  0  0  0            999 V2000
   -5.3445   -0.5046    0.1861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6722    0.5419    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2770    1.6638    0.8038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.5353   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730   -0.6243   -0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -0.6771   -1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336    0.4774   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    0.4854   -1.5989 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6290    0.1157   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -1.1913   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885   -1.5111    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -0.5324    1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -0.8488    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716    0.7719    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    1.0775    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    1.6393   -0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237    1.6527   -0.1497 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475    1.9754    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3850   -1.5136   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -1.5957   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381    1.4564   -2.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747   -0.2703   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669   -1.9524   -0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -2.5395    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3072   -0.8563    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4902    1.5636    1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9044    2.1100    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174    2.5289   -0.5485 H   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
  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
  9 10  2  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
  7 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  4  1  0  0  0  0
 15  9  1  0  0  0  0
  3 18  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
  8 21  1  0  0  0  0
  8 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 13 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  0  0  0  0
 16 28  1  0  0  0  0
M  END


  Mrv1652306242117503D          

 28 29  0  0  0  0            999 V2000
   -5.3445   -0.5046    0.1861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6722    0.5419    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2770    1.6638    0.8038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.5353   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730   -0.6243   -0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -0.6771   -1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336    0.4774   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    0.4854   -1.5989 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6290    0.1157   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -1.1913   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8885   -1.5111    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -0.5324    1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -0.8488    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716    0.7719    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    1.0775    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567    1.6393   -0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237    1.6527   -0.1497 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475    1.9754    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3850   -1.5136   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -1.5957   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381    1.4564   -2.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7747   -0.2703   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669   -1.9524   -0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -2.5395    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3072   -0.8563    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4902    1.5636    1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9044    2.1100    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174    2.5289   -0.5485 H   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
  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
  9 10  2  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
  7 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  4  1  0  0  0  0
 15  9  1  0  0  0  0
  3 18  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
  8 21  1  0  0  0  0
  8 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 13 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  0  0  0  0
 16 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(C([H])=N1)C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO3/c15-11-4-1-9(2-5-11)7-10-3-6-12(13(16)17)14-8-10/h1-6,8,15H,7H2,(H,16,17)

> <INCHI_KEY>
SJBFZHNCSGBLEK-UHFFFAOYSA-N

> <FORMULA>
C13H11NO3

> <MOLECULAR_WEIGHT>
229.235

> <EXACT_MASS>
229.073893218

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.29107977444493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(4-hydroxyphenyl)methyl]pyridine-2-carboxylic acid

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
1.0944074550358218

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.117239043798106

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1077592505336131

> <JCHEM_PKA_STRONGEST_BASIC>
5.709586639949793

> <JCHEM_POLAR_SURFACE_AREA>
70.42

> <JCHEM_REFRACTIVITY>
62.503400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenopicolinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -5.345  -0.505   0.186  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.672   0.542   0.263  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.277   1.664   0.804  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.300   0.535  -0.212  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.773  -0.624  -0.737  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.483  -0.677  -1.198  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.734   0.477  -1.115  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.676   0.485  -1.599  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.629   0.116  -0.517  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.006  -1.191  -0.278  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.889  -1.511   0.728  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.433  -0.532   1.540  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.328  -0.849   2.562  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.072   0.772   1.320  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.184   1.077   0.306  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.257   1.639  -0.591  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.524   1.653  -0.150  0.00  0.00           N+0
HETATM   18  H   UNK     0      -4.947   1.975   1.717  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.385  -1.514  -0.789  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.050  -1.596  -1.619  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.938   1.456  -2.040  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.775  -0.270  -2.406  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.567  -1.952  -0.929  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.167  -2.539   0.894  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.307  -0.856   2.315  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.490   1.564   1.952  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.904   2.110   0.139  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.617   2.529  -0.549  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   18                                                       
CONECT    4    2    5   17                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   21   22                                             
CONECT    9    8   10   15                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   25                                                       
CONECT   14   12   15   26                                                  
CONECT   15   14    9   27                                                  
CONECT   16    7   17   28                                                  
CONECT   17   16    4                                                       
CONECT   18    3                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
CONECT   21    8                                                            
CONECT   22    8                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   16                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-[(4-Hydroxyphenyl)methyl]pyridine-2-carboxylate	Generator
Phenopicolinate	Generator

Chemical Formula

C₁₃H₁₁NO₃

Average Mass

229.2350 Da

Monoisotopic Mass

229.07389 Da

IUPAC Name

5-[(4-hydroxyphenyl)methyl]pyridine-2-carboxylic acid

Traditional Name

phenopicolinic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=NC=C(CC2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C13H11NO3/c15-11-4-1-9(2-5-11)7-10-3-6-12(13(16)17)14-8-10/h1-6,8,15H,7H2,(H,16,17)

InChI Key

SJBFZHNCSGBLEK-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Paecilomyces	NPAtlas	1150540

Species Where Detected

Species Name	Source	Reference
Paecilomyces sp. AF2562	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 5-alkyl-2-carboxypyrimidines. These are pyrimidine-2-carboxylic acids that carry an alkyl group at the 5-position of the pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

5-alkyl-2-carboxypyrimidines

Alternative Parents

Substituents

5-alkyl-2-carboxypyrimidine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	2.91	ALOGPS
logP	1.09	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.11	ChemAxon
pKa (Strongest Basic)	5.71	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.5 m³·mol⁻¹	ChemAxon
Polarizability	23.29 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

NPAtlas ID

NPA021153

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018048

Chemspider ID

2306742

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

Nakamura T, Yasuda H, Obayashi A, Tanabe O, Matsumura S: Phenopicolinic acid, a new microbial product inhibiting dopamine beta-hydroxylase. J Antibiot (Tokyo). 1975 Jun;28(6):477-8. doi: 10.7164/antibiotics.28.477. [PubMed:1150540 ]

Showing NP-Card for Phenopicolinic acid (NP0003807)

MOL for NP0003807 (Phenopicolinic acid)

3D MOL for NP0003807 (Phenopicolinic acid)

3D SDF for NP0003807 (Phenopicolinic acid)

3D-SDF for NP0003807 (Phenopicolinic acid)

PDB for NP0003807 (Phenopicolinic acid)

3D PDB for NP0003807 (Phenopicolinic acid)

SMILES for NP0003807 (Phenopicolinic acid)

INCHI for NP0003807 (Phenopicolinic acid)

Structure for NP0003807 (Phenopicolinic acid)

3D Structure for NP0003807 (Phenopicolinic acid)