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Showing metabocard for 2-Hydroxypyridine (HMDB0013751)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:50 UTC
Update Date2023-02-21 17:18:02 UTC
HMDB IDHMDB0013751
Secondary Accession Numbers
  • HMDB13751
Metabolite Identification
Common Name2-Hydroxypyridine
DescriptionThis colourless crystalline solid is used in peptide synthesis. It is well known to form hydrogen bonded structures somewhat related to the base-pairing mechanism found in RNA and DNA. It is also a classic case of a molecule that exists as tautomers. Some publications only focus one of the two possible patterns, and neglect the influence of the other. For example, to calculation of the energy difference of the two tautomers in a non-polar solution will lead to a wrong result if a large quantity of the substance is on the side of the dimer in an equilibrium. The direct tautomerisation is not energetically favoured, but a dimerisation followed by a double proton transfer and dissociation of the dimer is a self catalytic path from one tautomer to the other. Protic solvents also mediate the proton transfer during the tautomerisation.
Structure
Data?1676999882
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013751 (2-Hydroxypyridine)

 
  Mrv1652304202019402D          
 
  7  7  0  0  0  0            999 V2000
   11.1938   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -9.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9018   -9.5299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -7.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0013751 (2-Hydroxypyridine)

HMDB0013751
     RDKit          3D
2-Hydroxypyridine
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.5645    0.1441   -0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    0.1626   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -1.0285   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829   -1.0550    0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714    0.1380    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871    1.3141   -0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624    1.3057   -0.2453 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0735    0.6108    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568   -1.9585    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.0083    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6508    0.1193    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228    2.2556   -0.1780 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  7  2  0
  7  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
M  END
Download

3D SDF for HMDB0013751 (2-Hydroxypyridine)

 
  Mrv1652304202019402D          
 
  7  7  0  0  0  0            999 V2000
   11.1938   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -9.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9018   -9.5299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -7.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013751

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)

> <INCHI_KEY>
UBQKCCHYAOITMY-UHFFFAOYSA-N

> <FORMULA>
C5H5NO

> <MOLECULAR_WEIGHT>
95.0993

> <EXACT_MASS>
95.037113787

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.200287283659224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridin-2-ol

> <ALOGPS_LOGP>
0.64

> <JCHEM_LOGP>
1.0464655973333332

> <ALOGPS_LOGS>
0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.700690095151401

> <JCHEM_PKA_STRONGEST_BASIC>
2.429271976905061

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
26.195499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-pyridone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0013751 (2-Hydroxypyridine)

HMDB0013751
     RDKit          3D
2-Hydroxypyridine
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.5645    0.1441   -0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    0.1626   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -1.0285   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829   -1.0550    0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714    0.1380    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8871    1.3141   -0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624    1.3057   -0.2453 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0735    0.6108    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568   -1.9585    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133   -2.0083    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6508    0.1193    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228    2.2556   -0.1780 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  7  2  0
  7  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
M  END
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PDB for HMDB0013751 (2-Hydroxypyridine)

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      20.895 -17.023   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.895 -15.483   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      19.552 -17.810   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0      22.217 -17.789   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      19.552 -14.716   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.230 -17.023   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.230 -15.483   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    7                                                       
CONECT    7    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0013751 (2-Hydroxypyridine)

COMPND    HMDB0013751
HETATM    1  O1  UNL     1       2.565   0.144  -0.310  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.177   0.163  -0.190  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.494  -1.028  -0.008  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.883  -1.055   0.116  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.571   0.138   0.053  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.887   1.314  -0.128  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.462   1.306  -0.245  1.00  0.00           N  
HETATM    8  H1  UNL     1       3.073   0.611   0.440  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.057  -1.958   0.039  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.413  -2.008   0.261  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.651   0.119   0.150  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.423   2.256  -0.178  1.00  0.00           H  
CONECT    1    2    8
CONECT    2    3    3    7
CONECT    3    4    9
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7   12
END
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SMILES for HMDB0013751 (2-Hydroxypyridine)

OC1=CC=CC=N1
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INCHI for HMDB0013751 (2-Hydroxypyridine)

InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-PyridinolChEBI
2-PyridoneChEBI
1-Hydroxy-2-pyridineHMDB
1H-Pyridin-2-oneHMDB
2(1H)-PyridinoneHMDB
2(1H)-PyridoneHMDB
2-OxopyridineHMDB
2-Pyridinol (acd/name 4.0)HMDB
2-PyridinoneHMDB
2-PyridolHMDB
alpha -PyridoneHMDB
alpha-PyridoneHMDB
Pyridin-2-olHMDB
Pyridone-2HMDB
2-Hydroxypyridine sodium saltHMDB
2-HydroxypyridineChEBI
Chemical FormulaC5H5NO
Average Molecular Weight95.0993
Monoisotopic Molecular Weight95.037113787
IUPAC Namepyridin-2-ol
Traditional Name2-pyridone
CAS Registry Number142-08-5
SMILES
OC1=CC=CC=N1
InChI Identifier
InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)
InChI KeyUBQKCCHYAOITMY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentPyridinones
Alternative Parents
Substituents
  • Pyridinone
  • Dihydropyridine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen 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 Point107.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available115.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00002167
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 SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112195
KNApSAcK IDC00007405
Chemspider ID8537
KEGG Compound IDC02502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Pyridone
METLIN IDNot Available
PubChem Compound8871
PDB IDNot Available
ChEBI ID16540
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nhan DD, Carvalho FP, Nam BQ: Fate of 14C-chlorpyrifos in the tropical estuarine environment. Environ Technol. 2002 Nov;23(11):1229-34. [PubMed:12472153 ]
  2. Menon R, Tolbert D, Cefali E: The comparative bioavailability of an extended-release niacin and lovastatin fixed dose combination tablet versus extended-release niacin tablet, lovastatin tablet and a combination of extended-release niacin tablet and lovastatin tablet. Biopharm Drug Dispos. 2007 Sep;28(6):297-306. [PubMed:17571283 ]