NP-MRD: Showing NP-Card for 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate (NP0087683)

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Record Information

Version

2.0

Created at

2022-05-11 16:56:48 UTC

Updated at

2022-05-11 16:56:48 UTC

NP-MRD ID

NP0087683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate

Description

2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate, also known as 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid or 5-formyl-3-hydroxy-2-methylisonicotinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate is a moderately basic compound (based on its pKa). In humans, 2-methyl-3-hydroxy-5-formylpyridine-4-carboxylate is involved in the metabolic disorder called the hypophosphatasia pathway. A pyridinemonocarboxylic acid that is pyridine-4-carboxylic acid substituted by a methyl group, hydroxy group and formyl group at positions 2,3 and 5, respectively.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220562D          

 13 13  0  0  0  0            999 V2000
   14.9650  -10.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2505   -9.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2505   -9.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361   -8.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216   -9.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216   -9.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361  -10.2855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1071   -8.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361   -7.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -8.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3927   -9.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2505   -7.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216   -7.3980    0.0000 O   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
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=NC=C(C=O)C(C(O)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2-3,11H,1H3,(H,12,13)

> <INCHI_KEY>
JTWNWNJMNSJYDL-UHFFFAOYSA-N

> <FORMULA>
C8H7NO4

> <MOLECULAR_WEIGHT>
181.1455

> <EXACT_MASS>
181.037507717

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.371586057138806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.38134763627945817

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.585262402745876

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.289801127456996

> <JCHEM_PKA_STRONGEST_BASIC>
2.6475706703452264

> <JCHEM_POLAR_SURFACE_AREA>
87.49000000000001

> <JCHEM_REFRACTIVITY>
44.3137

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      27.935 -19.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.601 -18.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.601 -16.890   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.267 -16.120   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.934 -16.890   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.934 -18.430   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      25.267 -19.200   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      22.600 -16.120   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.267 -14.580   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      27.935 -16.120   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      21.266 -16.890   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.601 -13.810   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.934 -13.810   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6                                                       
CONECT    8    5   11                                                       
CONECT    9    4   12   13                                                  
CONECT   10    3                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylic acid	ChEBI
5-Formyl-3-hydroxy-2-methyl-4-pyridinecarboxylic acid	ChEBI
5-Formyl-3-hydroxy-2-methylisonicotinic acid	ChEBI
5-Formyl-3-hydroxy-2-methylpyridine-4-carboxylate	Kegg
5-Formyl-3-hydroxy-2-methyl-4-pyridinecarboxylate	Generator
5-Formyl-3-hydroxy-2-methylisonicotinate	Generator
5-Formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid	Generator

Chemical Formula

C₈H₇NO₄

Average Mass

181.1455 Da

Monoisotopic Mass

181.03751 Da

IUPAC Name

5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid

Traditional Name

5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=NC=C(C=O)C(C(O)=O)=C1O

InChI Identifier

InChI=1S/C8H7NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2-3,11H,1H3,(H,12,13)

InChI Key

JTWNWNJMNSJYDL-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
3-pyridine carboxaldehyde
Aryl-aldehyde
Hydroxypyridine
Methylpyridine
Vinylogous acid
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Aldehyde
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:28038 )
pyridinecarbaldehyde (CHEBI:28038 )
methylpyridines (CHEBI:28038 )

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	0.5	ALOGPS
logP	0.38	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	2.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.31 m³·mol⁻¹	ChemAxon
Polarizability	16.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon