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Showing metabocard for Methyl nicotinate (HMDB0029806)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:45 UTC
Update Date2020-02-26 21:44:27 UTC
HMDB IDHMDB0029806
Secondary Accession Numbers
  • HMDB29806
Metabolite 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 . The hydrolysis is thought to be mediated by nonspecific α-naphthylacetate-esterase at the dermis layer of the skin .
Structure
Data?1582753467
MOLSDFPDBSMILESInChI
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 Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point38 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility47.6 mg/mL at 20 °CNot Available
LogP0.83Not Available
Predicted Properties
PropertyValueSource
Water Solubility193 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9400000000-7c3a8027277de3a14a41Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9400000000-7c3a8027277de3a14a41Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2900000000-3915717ccabc67393833Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-e85db02b4f474d26b636Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-d9503a788323d33eecd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-9600000000-c54c379ee39a53af4ff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-32eb9e18a26af57d26c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-5685ba3190b1d8797adbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9600000000-22a2e3fff8ba9d56edc0Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13882
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .