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Showing NP-Card for 3-Hydroxypyridine (NP0083778)

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Record Information
Version2.0
Created at2022-04-29 04:43:06 UTC
Updated at2022-04-29 04:43:06 UTC
NP-MRD IDNP0083778
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxypyridine
Description3-Pyridinol, also known as 3-hydroxypyridine, belongs to the class of organic compounds known as hydroxypyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a hydroxyl group. 3-Hydroxypyridine is found in Capsicum annuum, Paeonia lactiflora, Paeonia suffruticosa, Salvia divinorum and Triticum aestivum . 3-Hydroxypyridine was first documented in 2014 (PMID: 23543363). 3-Pyridinol is a very strong basic compound (based on its pKa) (PMID: 25894772).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083778 (3-Hydroxypyridine)


  Mrv1652305062021422D          

  7  7  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
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3D MOL for NP0083778 (3-Hydroxypyridine)

     RDKit          3D

 12 12  0  0  0  0  0  0  0  0999 V2000
   -2.2809    0.5316   -0.0188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9511    0.1478   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    1.1295    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3297    0.7454    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -0.5842    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748   -1.4952   -0.0393 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6257   -1.1857   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0206   -0.1648   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357    2.1892    0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364    1.5069    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023   -0.9004    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976   -1.9202   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  1  8  1  0
  7 12  1  0
  5 11  1  0
  4 10  1  0
  3  9  1  0
M  END
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3D SDF for NP0083778 (3-Hydroxypyridine)


  Mrv1652305062021422D          

  7  7  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CN=CC=C1

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

> <INCHI_KEY>
GRFNBEZIAWKNCO-UHFFFAOYSA-N

> <FORMULA>
C5H5NO

> <MOLECULAR_WEIGHT>
95.0993

> <EXACT_MASS>
95.037113787

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.157784749521909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridin-3-ol

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
0.4520080673333333

> <ALOGPS_LOGS>
0.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.15957569012975

> <JCHEM_PKA_STRONGEST_BASIC>
5.260338754466453

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
25.881999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.04e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxypyridine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0083778 (3-Hydroxypyridine)

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PDB for NP0083778 (3-Hydroxypyridine)
HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    5    6                                                       
CONECT    5    2    4    7                                                  
CONECT    6    3    4                                                       
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0083778 (3-Hydroxypyridine)
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SMILES for NP0083778 (3-Hydroxypyridine)
OC1=CN=CC=C1
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INCHI for NP0083778 (3-Hydroxypyridine)
InChI=1S/C5H5NO/c7-5-2-1-3-6-4-5/h1-4,7H
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Synonyms
ValueSource
3-HydroxypyridineChEBI
3-PyridolChEBI
beta-HydroxypyridineChEBI
m-HydroxypyridineChEBI
b-HydroxypyridineGenerator
Β-hydroxypyridineGenerator
3-Hydroxypyridine hydrochlorideMeSH
3-Hydroxypyridine isomerMeSH
3-Hydroxypyridine, silver (1+) saltMeSH
3-HydroxypyridiniumMeSH
3-Hydroxypyridine, sodium saltMeSH
Chemical FormulaC5H5NO
Average Mass95.0993 Da
Monoisotopic Mass95.03711 Da
IUPAC Namepyridin-3-ol
Traditional Name3-hydroxypyridine
CAS Registry NumberNot Available
SMILES
OC1=CN=CC=C1
InChI Identifier
InChI=1S/C5H5NO/c7-5-2-1-3-6-4-5/h1-4,7H
InChI KeyGRFNBEZIAWKNCO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Capsicum annuumLOTUS Database
Paeonia lactifloraLOTUS Database
Paeonia suffruticosaLOTUS Database
Salvia divinorumLOTUS Database
Triticum aestivumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxypyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a hydroxyl group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassHydroxypyridines  
Direct ParentHydroxypyridines  
Alternative Parents
Substituents
  • Hydroxypyridine
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.08ALOGPS
logP0.45ChemAxon
logS0.72ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.88 m³·mol⁻¹ChemAxon
Polarizability9.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062033  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-12318  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7971  
PDB IDNot Available
ChEBI ID87440  
Good Scents IDNot Available
References
General References
  1. Karvelis L, Gasparaviciute R, Klimavicius A, Janciene R, Stankeviciute J, Meskys R: Pusillimonas sp. 5HP degrading 5-hydroxypicolinic acid. Biodegradation. 2014 Feb;25(1):11-9. doi: 10.1007/s10532-013-9636-3. Epub 2013 Mar 30. [PubMed:23543363  ] 
  2. Volchegorskii IA, Miroshnichenko IY, Rassokhina LM, Faizullin RM, Malkin MP, Pryakhina KE, Kalugina AV: Comparative analysis of the anxiolytic effects of 3-hydroxypyridine and succinic acid derivatives. Bull Exp Biol Med. 2015 Apr;158(6):756-61. doi: 10.1007/s10517-015-2855-3. Epub 2015 Apr 21. [PubMed:25894772  ]