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Showing metabocard for 3-Hydroxypicolinic acid (HMDB0013188)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-11-30 15:50:39 UTC
Update Date2023-02-21 17:17:55 UTC
HMDB IDHMDB0013188
Secondary Accession Numbers
  • HMDB13188
Metabolite Identification
Common Name3-Hydroxypicolinic acid
Description3-Hydroxypicolinic acid, also known as HPA, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Based on a literature review a significant number of articles have been published on 3-Hydroxypicolinic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013188 (3-Hydroxypicolinic acid)

  Mrv1652303102016502D          

 10 10  0  0  0  0            999 V2000
   11.0928  -11.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2678  -11.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8553  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2678  -10.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0928  -10.0721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5053  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8553   -9.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2678   -8.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303   -9.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303  -10.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  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  7  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for HMDB0013188 (3-Hydroxypicolinic acid)

HMDB0013188
     RDKit          3D
3-Hydroxypicolinic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.7175    1.1055    0.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    0.0655    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -1.0985    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -0.0867    0.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0516   -1.3343    0.2356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2615   -1.5034    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927   -0.4328   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934    0.8325   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    0.9889   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857    2.2497   -0.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -2.0129    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7089   -2.5014    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -0.6136   -0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    1.7045   -0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    2.6372   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
 10 15  1  0
M  END
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3D SDF for HMDB0013188 (3-Hydroxypicolinic acid)

  Mrv1652303102016502D          

 10 10  0  0  0  0            999 V2000
   11.0928  -11.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2678  -11.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8553  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2678  -10.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0928  -10.0721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5053  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8553   -9.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2678   -8.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303   -9.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303  -10.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  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  7  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013188

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=C(O)C=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-3,8H,(H,9,10)

> <INCHI_KEY>
BRARRAHGNDUELT-UHFFFAOYSA-N

> <FORMULA>
C6H5NO3

> <MOLECULAR_WEIGHT>
139.1088

> <EXACT_MASS>
139.026943031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.21695586881242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxypyridine-2-carboxylic acid

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
-0.5213333799091218

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.90657626436559

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.41070724176744067

> <JCHEM_PKA_STRONGEST_BASIC>
6.124763450634564

> <JCHEM_POLAR_SURFACE_AREA>
70.42

> <JCHEM_REFRACTIVITY>
32.7662

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxypicolinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0013188 (3-Hydroxypicolinic acid)

HMDB0013188
     RDKit          3D
3-Hydroxypicolinic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.7175    1.1055    0.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546    0.0655    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -1.0985    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -0.0867    0.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0516   -1.3343    0.2356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2615   -1.5034    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927   -0.4328   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934    0.8325   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    0.9889   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857    2.2497   -0.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -2.0129    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7089   -2.5014    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -0.6136   -0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    1.7045   -0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    2.6372   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
 10 15  1  0
M  END
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PDB for HMDB0013188 (3-Hydroxypicolinic acid)

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      20.707 -21.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.167 -21.469   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.397 -20.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.167 -18.801   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      20.707 -18.801   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      21.477 -20.135   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.397 -17.468   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.167 -16.134   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      16.857 -17.468   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.857 -20.135   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0013188 (3-Hydroxypicolinic acid)

COMPND    HMDB0013188
HETATM    1  O1  UNL     1       2.717   1.105   0.142  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.055   0.066   0.233  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.814  -1.098   0.495  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.616  -0.087   0.102  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.052  -1.334   0.236  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.261  -1.503   0.121  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.093  -0.433  -0.134  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.593   0.832  -0.277  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.197   0.989  -0.152  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.286   2.250  -0.296  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.506  -2.013   0.262  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.709  -2.501   0.228  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.172  -0.614  -0.222  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.199   1.705  -0.477  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.179   2.637  -0.260  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5    9
CONECT    5    6
CONECT    6    7    7   12
CONECT    7    8   13
CONECT    8    9    9   14
CONECT    9   10
CONECT   10   15
END
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SMILES for HMDB0013188 (3-Hydroxypicolinic acid)

OC(=O)C1=C(O)C=CC=N1
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INCHI for HMDB0013188 (3-Hydroxypicolinic acid)

InChI=1S/C6H5NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-3,8H,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Hydroxy-2-pyridinecarboxylic acidChEBI
HPAChEBI
3-Hydroxy-2-pyridinecarboxylateGenerator
3-HydroxypicolinateGenerator
3-Hydroxypyridine-2-carboxylic acidHMDB
3-Hydroxypyridine-2-carboxylateHMDB
Chemical FormulaC6H5NO3
Average Molecular Weight139.1088
Monoisotopic Molecular Weight139.026943031
IUPAC Name3-hydroxypyridine-2-carboxylic acid
Traditional Name3-hydroxypicolinic acid
CAS Registry Number874-24-8
SMILES
OC(=O)C1=C(O)C=CC=N1
InChI Identifier
InChI=1S/C6H5NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-3,8H,(H,9,10)
InChI KeyBRARRAHGNDUELT-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Hydroxypyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029323
KNApSAcK IDNot Available
Chemspider ID12827
KEGG Compound IDC18620
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxypicolinic_acid
METLIN IDNot Available
PubChem Compound13401
PDB IDNot Available
ChEBI ID64342
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available