Record Information
Version1.0
Creation date2010-04-08 22:10:12 UTC
Update date2018-05-29 00:58:39 UTC
Primary IDFDB012485
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNicotinamide
DescriptionWidespread in plants, e.g. rice, yeast and fungi. Dietary supplement, may be used in infant formulas Nicotinamide, also known as niacinamide and nicotinic acid amide, is the amide of nicotinic acid (vitamin B3 / niacin). Nicotinamide is a water-soluble vitamin and is part of the vitamin B group. Nicotinic acid, also known as niacin, is converted to nicotinamide in vivo, and, though the two are identical in their vitamin functions, nicotinamide does not have the same pharmacologic and toxic effects of niacin, which occur incidental to niacin's conversion. Nicotinamide is found in many foods, some of which are soursop, gooseberry, peach (variety), and kumquat.
CAS Number98-92-0
Structure
Thumb
Synonyms
SynonymSource
3-PyridinecarboxamideChEBI
beta-PyridinecarboxamideChEBI
NiacinChEBI
NicotinamidChEBI
Nicotinic acid amideChEBI
NicotinsaeureamidChEBI
NikotinamidChEBI
NikotinsaeureamidChEBI
Vitamin b3ChEBI
Vitamin PPChEBI
NicotinamideKegg
b-PyridinecarboxamideGenerator
Β-pyridinecarboxamideGenerator
Nicotinate amideGenerator
3-CarbamoylpyridineHMDB
3-Pyridinecarboxylic acid amideHMDB
Acid amideHMDB
Amid kyseliny nikotinoveHMDB
Amide PPHMDB
AminicotinHMDB
AmixicotynHMDB
AmnicotinHMDB
Austrovit PPHMDB
BenicotHMDB
Delonin amideHMDB
DipegylHMDB
DipigylHMDB
EndobionHMDB
Factor PPHMDB
HansamidHMDB
Inovitan PPHMDB
m-(Aminocarbonyl)pyridineHMDB
MediatricHMDB
NAMHMDB
Nandervit-NHMDB
NiacevitHMDB
NiamideHMDB
Niavit PPHMDB
NicamideHMDB
NicaminaHMDB
NicamindonHMDB
NicasirHMDB
NicobionHMDB
NicofortHMDB
NicogenHMDB
NicomidolHMDB
Nicosan 2HMDB
NicosylamideHMDB
NicotaHMDB
NicotamideHMDB
NicotilamideHMDB
NicotililamidoHMDB
NicotinamidaHMDB
NicotinamidumHMDB
Nicotine acid amideHMDB
Nicotine amideHMDB
Nicotinic amideHMDB
NicotinsaureamidHMDB
NicotolHMDB
NicotylamideHMDB
NicotylamidumHMDB
NicovelHMDB
NicovitHMDB
NicovitinaHMDB
NicovitolHMDB
NicozyminHMDB
NictoamideHMDB
Niko-taminHMDB
NiocinamideHMDB
NiozyminHMDB
PapulexHMDB
PelminHMDB
PelmineHMDB
Pelonin amideHMDB
PP-FaktorHMDB
Propamine aHMDB
Pyridine-3-carboxylic acid amideHMDB
SavacotylHMDB
Vi-nicotylHMDB
Vi-noctylHMDB
Witamina PPHMDB
3 PyridinecarboxamideHMDB
Astra brand OF niacinamideHMDB
b 3, VitaminHMDB
Niacinamide merck brandHMDB
Pharmagenix brand OF niacinamideHMDB
b3, VitaminHMDB
EnduramideHMDB
Jenapharm, nicotinsäureamidHMDB
Niacinamide jenapharm brandHMDB
Niacinamide pharmagenix brandHMDB
Jenapharm brand OF niacinamideHMDB
Nicotinsäureamid jenapharmHMDB
Vitamin b 3HMDB
Merck brand OF niacinamideHMDB
Niacinamide astra brandHMDB
β-Pyridinecarboxamidebiospider
3-(Aminocarbonyl)pyridinebiospider
3-Amidopyridinebiospider
6-Aminonicotinamidebiospider
Niacinamidedb_source
Vitamin B3 (Nicotinamide)biospider
Vitamin PP (Nicotinamide)biospider
β-pyridinecarboxamideGenerator
Predicted Properties
PropertyValueSource
Water Solubility50.1 g/LALOGPS
logP-0.45ALOGPS
logP-0.39ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)3.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.98 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability11.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H6N2O
IUPAC namepyridine-3-carboxamide
InChI IdentifierInChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
InChI KeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
Isomeric SMILESNC(=O)C1=CC=CN=C1
Average Molecular Weight122.1246
Monoisotopic Molecular Weight122.048012824
Classification
Description belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 59.01%; H 4.95%; N 22.94%; O 13.10%DFC
Melting PointMp 129-130°DFC
Boiling PointBp0.0005 150-160°DFC
Experimental Water Solubility500 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logP-0.37HANSCH,C ET AL. (1995)
Experimental pKapKa 3.33 (20°)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)splash10-004i-0900000000-acb6a21304b0c09c8472View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd538View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9500000000-790385e574240b8d39deView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2910000000-d760b65bb76d6464038eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-4900000000-47c6f72d1bb5465c1376View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-1809e537780b814af0c9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-c4a5ff5285417499eff8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-0e84a60cc2a2d44704f4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-acb6a21304b0c09c8472View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd538View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9500000000-790385e574240b8d39deView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2910000000-d760b65bb76d6464038eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-4900000000-47c6f72d1bb5465c1376View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-23a567506bfbc259e77cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-8900000000-931c139355be3ef594f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-2900000000-72a7c92eb2667f5b6c3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kor-9800000000-89d56b6cb7e033699d24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-eed71abbb10ba926c13dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-3900000000-0c62aa6aba6e23b6c195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9100000000-4357a8833611d1756c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-c9685717817d0081fe6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f6d71a6c467f84ddd6abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-62c4bd312efbfa37d1a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-05714b528dc84942b9dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-edb6a77c0dfdcbdacc5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-eed71abbb10ba926c13dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-3900000000-0c62aa6aba6e23b6c195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-4357a8833611d1756c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-c9685717817d0081fe6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-960acce7ead55399b5dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c7ec333d35eb740520aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9600000000-466f98885e2efba73575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9200000000-6ef8d7e5edcdd0b02758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-f38177aa475e58941088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-6a883d82fcd7c450f6ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-882d0c59d946a5087b9fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0kor-9600000000-2b1c5667d92bc1b80b36View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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 ID911
ChEMBL IDCHEMBL1140
KEGG Compound IDC00153
Pubchem Compound ID936
Pubchem Substance IDNot Available
ChEBI ID17154
Phenol-Explorer IDNot Available
DrugBank IDDB02701
HMDB IDHMDB01406
CRC / DFC (Dictionary of Food Compounds) IDHHJ27-Z:HHJ27-Z
EAFUS ID2662
Dr. Duke IDNICOTINIC-ACID-AMIDE|NICOTINAMIDE
BIGG ID34058
KNApSAcK IDC00000209
HET IDNCA
Flavornet IDNot Available
GoodScent IDrw1068911
SuperScent IDNot Available
Wikipedia IDNiacinamide
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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
depressantDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048 map00760
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).