Record Information
Version1.0
Creation date2010-04-08 22:04:48 UTC
Update date2018-05-28 22:37:10 UTC
Primary IDFDB001014
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNicotinic acid
DescriptionPresent in fruits and other plant materials. Nutrient supplement. Vitamin, enzyme cofactor [DFC] Niacin (also known as vitamin B3, nicotinic acid and vitamin PP) is an organic compound with the formula C6H5NO2 and, depending on the definition used, one of the forty to eighty essential human nutrients. This colorless, water-soluble solid is a derivative of pyridine, with a carboxyl group (COOH) at the 3-position. Other forms of vitamin B3 include the corresponding amide, nicotinamide ("niacinamide"), where the carboxyl group has been replaced by a carboxamide group (CONH2), as well as more complex amides and a variety of esters. The terms niacin, nicotinamide, and vitamin B3 are often used interchangeably to refer to any member of this family of compounds, since they have the same biochemical activity. [Wikipedia]. Nicotinic acid is found in many foods, some of which are cold cut, garden onion (variety), napa cabbage, and horseradish tree.
CAS Number59-67-6
Structure
Thumb
Synonyms
SynonymSource
3-CarboxypyridineChEBI
3-Pyridinecarboxylic acidChEBI
3-Pyridylcarboxylic acidChEBI
Acide nicotiniqueChEBI
Acido nicotinicoChEBI
Acidum nicotinicumChEBI
Anti-pellagra vitaminChEBI
beta-Pyridinecarboxylic acidChEBI
m-Pyridinecarboxylic acidChEBI
NiacinChEBI
NikotinsaeureChEBI
P.P. factorChEBI
Pellagra preventive factorChEBI
PP FactorChEBI
Pyridine-beta-carboxylic acidChEBI
Vitamin b3ChEBI
NiacorKegg
NiaspanKegg
3-PyridinecarboxylateGenerator
3-PyridylcarboxylateGenerator
b-PyridinecarboxylateGenerator
b-Pyridinecarboxylic acidGenerator
beta-PyridinecarboxylateGenerator
Β-pyridinecarboxylateGenerator
Β-pyridinecarboxylic acidGenerator
m-PyridinecarboxylateGenerator
Pyridine-b-carboxylateGenerator
Pyridine-b-carboxylic acidGenerator
Pyridine-beta-carboxylateGenerator
Pyridine-β-carboxylateGenerator
Pyridine-β-carboxylic acidGenerator
NicotinateGenerator
3-CarboxylpyridineHMDB
AkotinHMDB
ApelagrinHMDB
DaskilHMDB
EfacinHMDB
EnduracinHMDB
LinicHMDB
NiacHMDB
NiacineHMDB
NicacidHMDB
NicaminHMDB
NicanginHMDB
Nico-spanHMDB
NicobidHMDB
NicocapHMDB
NicodelmineHMDB
NicolarHMDB
NiconacidHMDB
Nicosan 3HMDB
NicotinipcaHMDB
NicylHMDB
NyclinHMDB
PellagrinHMDB
PeloninHMDB
Slo-niacinHMDB
WampocapHMDB
Aluminum salt, niacinHMDB
InduracinHMDB
Niacin cobalt (2+) saltHMDB
Niacin iron (2+) saltHMDB
Niacin lithium saltHMDB
Niacin magnesium saltHMDB
Niacin sodium saltHMDB
Nico-400HMDB
Potassium salt, niacinHMDB
Sodium salt, niacinHMDB
Tosylate, niacinHMDB
Nicotinate, lithiumHMDB
Hydrochloride, niacinHMDB
Niacin aluminum saltHMDB
Niacin calcium saltHMDB
Niacin copper (2+) saltHMDB
Niacin hydrochlorideHMDB
Niacin lithium salt, hemihydrateHMDB
Nico400HMDB
Tartrate, niacinHMDB
3 Pyridinecarboxylic acidHMDB
Lithium nicotinateHMDB
Niacin ammonium saltHMDB
Niacin manganese (2+) saltHMDB
Niacin potassium saltHMDB
Niacin tartrateHMDB
Niacin tosylateHMDB
Niacin zinc saltHMDB
Nico 400HMDB
Niacin, USANdb_source
Niacor (TN)biospider
Niaspan (TN)biospider
Nicaginbiospider
Nico-Spanbiospider
Nicotinic acid, INNdb_source
Pyridine-β-carboxylic acidbiospider
Pyridine-3-carbonic acidbiospider
Pyridine-3-carboxylic acidbiospider
Pyridinecarboxylic acid, 3-biospider
Vitamin B3 (Niacin)manual
Vitamin PP (Niacin)manual
β-pyridinecarboxylateGenerator
β-pyridinecarboxylic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility83.1 g/LALOGPS
logP0.29ALOGPS
logP-0.17ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H5NO2
IUPAC namepyridine-3-carboxylic acid
InChI IdentifierInChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChI KeyPVNIIMVLHYAWGP-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CN=CC=C1
Average Molecular Weight123.1094
Monoisotopic Molecular Weight123.032028409
Classification
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
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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 Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 58.54%; H 4.09%; N 11.38%; O 25.99%DFC
Melting PointMp 236° (225-227°)DFC
Boiling PointNot Available
Experimental Water Solubility18 mg/mL at 20 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP0.36SANGSTER (1993)
Experimental pKapKa2 4.82 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-053i-0900000000-5daf0093df6c21c7279fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-053i-0900000000-f38b6609b45de8c74565View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0540-0900000000-4f55c81a6cd42f1b961dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-057r-5900000000-00bf3662b5b9db533c0aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0569-2900000000-7820ea736b03b71d2cb8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kmi-7900000000-9e4efda763cce5ddfe57View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-053i-0900000000-5daf0093df6c21c7279fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-053i-0900000000-f38b6609b45de8c74565View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0540-0900000000-4f55c81a6cd42f1b961dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-057r-5900000000-00bf3662b5b9db533c0aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0569-2900000000-7820ea736b03b71d2cb8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0540-0900000000-a701904fe6ded0abd98fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-9700000000-d7620f1dc8f42d1498b9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9600000000-c3303cf4e83870b3e656View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1900000000-27508608b33f1fb9f221View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-9100000000-a2037c9695659dceabd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-9100000000-4a2649a83ad2a40e5194View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kmi-7900000000-1bc47d1b1850f54fb7c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-1900000000-a352c5ce16d4b682b052View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-ab23ecb032e387b40bd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-02e37a1cfd3947037579View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-75d7e6658d2d6eca736eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0udi-9000000000-21a2d68d4f364c596f1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0ab9-0900000000-a74db528f61c435876c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-6900000000-773c08ab92ace4d48a9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00aj-9100000000-07b12fbe942e6c7fb12dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-005a-9000000000-66e0a5ba2ca8dbba1ed5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-fbf8ba47b56d7cc7be81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0900000000-eaf82f6ab0befde118e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00di-0900000000-eaf82f6ab0befde118e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9300000000-b1a48f694fba565108a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-a352c5ce16d4b682b052View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-ab23ecb032e387b40bd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-25068c42378f72756922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-6278a1e122005f48fcafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9000000000-e4e41ed9bef32955889eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4900000000-85d44ecd8ad348eeacd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-4911305982583ae20895View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4dea4a2d4a55907605eaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0kor-8900000000-7d3f033a49f5fad75f33View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID913
ChEMBL IDCHEMBL573
KEGG Compound IDC00253
Pubchem Compound ID938
Pubchem Substance IDNot Available
ChEBI ID15940
Phenol-Explorer IDNot Available
DrugBank IDDB00627
HMDB IDHMDB01488
CRC / DFC (Dictionary of Food Compounds) IDBPB04-S:BPB04-S
EAFUS ID2661
Dr. Duke IDNICOTINIC-ACID|NIACIN
BIGG ID34401
KNApSAcK IDC00000208
HET IDNIO
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNiacin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti acrodynic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti amblyopic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti anginal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti chilblainDUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Crohn's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti dysphagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti epileptic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hangover52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti hyperactivityDUKE
anti insomnic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Lyme33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti Meniere's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti pellagric52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Raynaud's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti schizophrenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti scotomic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thyrotoxic50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti vertigo52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cholereticDUKE
circulotonicDUKE
fibrinolyticDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypolipidemicDUKE
insulinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
insulinotonicDUKE
lipolyticDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
serotoninergic48278 DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
G-protein coupled receptor 109BGPR109BP49019
G-protein coupled receptor 109AGPR109AQ8TDS4
Purine nucleoside phosphorylasePNPP00491
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048 map00760
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.