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Showing NP-Card for pyridin-3-ylmethanol (NP0202833)

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Record Information
Version1.0
Created at2022-09-04 22:08:39 UTC
Updated at2022-09-04 22:08:39 UTC
NP-MRD IDNP0202833
Secondary Accession NumbersNone
Natural Product Identification
Common Namepyridin-3-ylmethanol
DescriptionNicotinyl alcohol, also known as 3-pyridylcarbinol or roniacol, belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. Nicotinyl alcohol is a strong basic compound (based on its pKa). It appears as a crystal that dissolves in water and alcohol with ease, also soluble in ether; melting range 147–148 ºC.Nicotinic acid is a brief peripheral vasodilator; this compound was made to make its action longer and effective. Fischer and Tebrock worked with this drug in more than two hundred patients for more than three years, achieving effective improvements, mainly in symptoms related to intermittent claudication, ulcer healing and others. Nicotinyl alcohol (pyridylcarbinol) is a niacin derivative used as a hypolipidemic agent and as a vasodilator. It provokes cutaneous flushing in head and upper thorax with heat, but with no major effects in blood pressure. It is used in peripheral vascular diseases, like arteriosclerosis obliterans, Raynaud's disease, thromboangiitis obliterans (Buerger's disease), arterial embolism, chilblains or migraine associated with vascular spasm. pyridin-3-ylmethanol is found in Crocus sativus. It was first documented in 1968 (PMID: 4883785). It causes flushing and may decrease blood pressure (PMID: 5796529) (PMID: 6346344).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0202833 (pyridin-3-ylmethanol)


  Mrv0541 02231217282D          

  8  8  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    0.0000    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
M  END
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3D MOL for NP0202833 (pyridin-3-ylmethanol)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.3106    1.0209    0.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523   -0.2636   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3656   -0.2711   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    0.8772    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    0.8987    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3943   -0.2625    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7244   -1.3812   -0.1408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3854   -1.4097   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377    1.3558   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796   -0.9465    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0989   -0.5774   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354    1.7882    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267    1.8142    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858   -0.3207    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -2.3224   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
M  END
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3D SDF for NP0202833 (pyridin-3-ylmethanol)


  Mrv0541 02231217282D          

  8  8  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    0.0000    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202833

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2

> <INCHI_KEY>
MVQVNTPHUGQQHK-UHFFFAOYSA-N

> <FORMULA>
C6H7NO

> <MOLECULAR_WEIGHT>
109.1259

> <EXACT_MASS>
109.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.227756199860899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridin-3-ylmethanol

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
-0.011776378333333407

> <ALOGPS_LOGS>
0.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.690153284532908

> <JCHEM_PKA_STRONGEST_BASIC>
4.728595177886644

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
30.716999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β pyridylcarbinol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0202833 (pyridin-3-ylmethanol)

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PDB for NP0202833 (pyridin-3-ylmethanol)
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  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0202833 (pyridin-3-ylmethanol)
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SMILES for NP0202833 (pyridin-3-ylmethanol)
OCC1=CC=CN=C1
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INCHI for NP0202833 (pyridin-3-ylmethanol)
InChI=1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2
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View in JSmol
Synonyms
ValueSource
3-(Hydroxymethyl)pyridineChEBI
3-Picolyl alcoholChEBI
3-PyridinylcarbinolChEBI
3-PyridinylmethanolChEBI
3-PyridylcarbinolChEBI
3-PyridylmethanolChEBI
beta-Picolyl alcoholChEBI
beta-PyridinecarbinolChEBI
beta-PyridylcarbinolChEBI
Nicotinic alcoholChEBI
Omega-hydroxy-3-picolineChEBI
Pyridine 3-methanolChEBI
Pyridine-3-carbinolChEBI
RoniacolKegg
b-Picolyl alcoholGenerator
Β-picolyl alcoholGenerator
b-PyridinecarbinolGenerator
Β-pyridinecarbinolGenerator
b-PyridylcarbinolGenerator
Β-pyridylcarbinolGenerator
3 HydroxymethylpyridineMeSH
RadecolMeSH
NicotinyltartrateMeSH
3-HydroxymethylpyridineMeSH
Ronicol retardMeSH
Alcohol, nicotinylMeSH
beta PyridylcarbinolMeSH
Alcohol, nicotinicMeSH
Nicomethanol hydrofluorideMeSH
RonicolMeSH
PyridylcarbinolMeSH
Pyridine-3-methanolMeSH
Hydrofluoride, nicomethanolMeSH
Pyridine 3 methanolMeSH
Nicotinyl alcoholMeSH, ChEBI
Chemical FormulaC6H7NO
Average Mass109.1259 Da
Monoisotopic Mass109.05276 Da
IUPAC Namepyridin-3-ylmethanol
Traditional Nameβ pyridylcarbinol
CAS Registry NumberNot Available
SMILES
OCC1=CC=CN=C1
InChI Identifier
InChI=1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2
InChI KeyMVQVNTPHUGQQHK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Crocus sativusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassNot Available
Direct ParentPyridines and derivatives  
Alternative Parents
Substituents
  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Alcohol
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP-0.13ALOGPS
logP-0.012ChemAxon
logS0.46ALOGPS
pKa (Strongest Acidic)14.69ChemAxon
pKa (Strongest Basic)4.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.72 m³·mol⁻¹ChemAxon
Polarizability11.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04145  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNicotinyl_alcohol  
METLIN IDNot Available
PubChem Compound7510  
PDB IDNot Available
ChEBI ID45213  
Good Scents IDNot Available
References
General References
  1. Gaut ZN, Taylor WJ: Effects of large doses of nicotinyl alcohol on serum lipid levels and carbohydrate tolerance. J Clin Pharmacol J New Drugs. 1968 Nov-Dec;8(6):370-6. doi: 10.1002/j.1552-4604.1968.tb00112.x. [PubMed:4883785  ] 
  2. Heiberg A: [Nicotinyl alcohol as a cholesterol-lowering agent]. Nord Med. 1969 May 29;81(22):698-700. [PubMed:5796529  ] 
  3. Dembinska-Kiec A, Korbut R, Bieron K, Kostka-Trabka E, Gryglewski RJ: beta-Pyridylcarbinol (Ronicol) releases a prostacyclin-like substance into arterial blood of patients with arteriosclerosis obliterans. Pharmacol Res Commun. 1983 Apr;15(4):377-85. doi: 10.1016/s0031-6989(83)80047-2. [PubMed:6346344  ] 
  4. LOTUS database [Link]