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Showing NP-Card for Methyl nicotinate (NP0045463)

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Record Information
Version2.0
Created at2022-03-17 19:20:24 UTC
Updated at2025-02-11 15:48:43 UTC
NP-MRD IDNP0045463
Natural Product DOIhttps://doi.org/10.57994/2864
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl nicotinate
DescriptionMethyl nicotinate, also known as heat spray or 3PYRCOOME, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Methyl nicotinate is a strong basic compound (based on its pKa). Methyl nicotinate is a herbal, tobacco, and warm tasting compound. Outside of the human body, Methyl nicotinate has been detected, but not quantified in, several different foods, such as alcoholic beverages, coffee and coffee products, fruits, nuts, and papaya. This could make methyl nicotinate a potential biomarker for the consumption of these foods. For veterinary purposes, methyl nicotinate is used to treat respiratory diseases, vascular disorders, rheumatoid arthritis, and muscle and joint pains. During tissue penetration at the dermis, methyl nicotinate is hydrolyzed to nicotinic acid. In humans, oral ingestion of 3-9 g of nicotinic acid per day resulted in "niacin hepatitis", gout, and impaired glucose intolerance within a short period of time. It was demonstrated in human subjects that the local cutaneous vascular response to methyl nicotinic was suppressed by inhibitors of prostaglandin biosynthesis, indicating that the effect of methyl nicotinate on vascular smooth muscles may be mediated by the release of local prostaglandins. Following topical administration, methyl nicotinate acts as a peripheral vasodilator to enhance local blood flow at the site of application. In human volunteers, topical administration of methyl nicotinate caused vasodilation-induced generalized cutaneous erythema. The action of methyl nicotinate as a rubefacient is thought to involve peripheral vasodilation. Prostaglandins released from the skin and blood vessels induce cutaneous vasodilation. Methyl nicotinate is found in Annona muricata , Areca catechu , Carica papaya, Chaenomeles speciosa, Coffea arabica, Daphne papyracea, Mycobacterium bovis, Mycobacterium tuberculosis, Osmanthus austrocaledonica and Osmanthus austrocaledonicus. Methyl nicotinate was first documented in 2012 (PMID: 22845897). The hydrolysis is thought to be mediated by nonspecific α-naphthylacetate-esterase at the dermis layer of the skin.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045463 (Methyl nicotinate)


  Mrv1652309061721352D          

 10 10  0  0  0  0            999 V2000
   -0.7088    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    0.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7055    1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4242    0.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312   -0.8164    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
  2  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for NP0045463 (Methyl nicotinate)

     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    3.3307    0.1891    0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9365    0.3755    0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0435   -0.5091   -0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008   -1.5772   -0.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -0.2918   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    0.8534    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625    1.0437    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    0.0760   -0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5647   -1.0314   -0.8119 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2201   -1.2306   -0.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128   -0.8819    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7741    0.6691   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7836    0.7042    1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    1.6181    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8514    1.9248    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2442    0.1996   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105   -2.1317   -1.1433 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
  3  5  1  0
  5 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
 10 17  1  0
  8 16  1  0
  7 15  1  0
  6 14  1  0
M  END
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3D SDF for NP0045463 (Methyl nicotinate)


  Mrv1652309061721352D          

 10 10  0  0  0  0            999 V2000
   -0.7088    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    0.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7055    1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4242    0.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4312   -0.8164    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
  2  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3

> <INCHI_KEY>
YNBADRVTZLEFNH-UHFFFAOYSA-N

> <FORMULA>
C7H7NO2

> <MOLECULAR_WEIGHT>
137.136

> <EXACT_MASS>
137.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.227195462506076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl pyridine-3-carboxylate

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.7590503530000002

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.244933443082692

> <JCHEM_POLAR_SURFACE_AREA>
39.19

> <JCHEM_REFRACTIVITY>
35.9264

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heat spray

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045463 (Methyl nicotinate)

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PDB for NP0045463 (Methyl nicotinate)
HEADER    PROTEIN                                 06-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-17         0                                  
HETATM    1  C   UNK     0      -1.323   0.778   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.007   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.342   0.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.672  -0.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.665  -1.556   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.330  -2.318   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.317   2.318   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.659   0.016   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.672  -1.524   0.000  0.00  0.00           C+0
CONECT    1    2    8    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    1                                                            
CONECT    9    1   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0045463 (Methyl nicotinate)
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SMILES for NP0045463 (Methyl nicotinate)
COC(=O)C1=CN=CC=C1
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INCHI for NP0045463 (Methyl nicotinate)
InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3
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Synonyms
ValueSource
Heat sprayKegg
Methyl nicotinic acidGenerator
3-(Carbomethoxy)pyridineHMDB
3-(Methoxycarbonyl)pyridineHMDB
3-CarbomethoxypyridineHMDB
3-Pyridinecarboxylic acid, methyl esterHMDB
3PyrCOOMeHMDB
FEMA 3709HMDB
m-(Methoxycarbonyl)pyridineHMDB
Methyl 3-pyridinecarboxylateHMDB
Methyl ester OF pyridine-3-carboxylic acidHMDB
Methyl-nicotinateHMDB
NicomethHMDB
Nicotinic acid methyl esterHMDB
Nicotinic acid, methyl esterHMDB
NikometHMDB
MethylnicotinateMeSH
Chemical FormulaC7H7NO2
Average Mass137.1360 Da
Monoisotopic Mass137.04768 Da
IUPAC Namemethyl pyridine-3-carboxylate
Traditional Nameheat spray
CAS Registry Number93-60-7
SMILES
COC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3
InChI KeyYNBADRVTZLEFNH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Annona muricataPlant
Areca catechuPlant
Carica papayaLOTUS Database
Carica papaya L.FooDB
Chaenomeles speciosaLOTUS Database
Coffea arabicaLOTUS Database
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Daphne papyraceaLOTUS Database
Mycobacterium bovisBacteria
Mycobacterium tuberculosisBacteria
Osmanthus austrocaledonicaPlant
Osmanthus austrocaledonicusLOTUS Database
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
    • 

  • Heteroaromatic compound
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • 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
logP0.45ALOGPS
logP0.76ChemAxon
logS0.15ALOGPS
pKa (Strongest Basic)3.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.19 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.93 m³·mol⁻¹ChemAxon
Polarizability13.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029806  
DrugBank IDDB13882  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001015  
KNApSAcK IDNot Available
Chemspider ID21111785  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7151  
PDB IDNot Available
ChEBI ID451700  
Good Scents IDNot Available
References
General References
  1. Zhao XJ, Hao F, Huang C, Rantalainen M, Lei H, Tang H, Wang Y: Systems responses of rats to mequindox revealed by metabolic and transcriptomic profiling. J Proteome Res. 2012 Sep 7;11(9):4712-21. doi: 10.1021/pr300533a. Epub 2012 Aug 15. [PubMed:22845897  ]