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Nicotinamide (FDB012485)

Record Information
Version1.0
Creation date2010-04-08 22:10:12 UTC
Update date2020-09-17 15:38:55 UTC
Primary IDFDB012485
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNicotinamide
DescriptionNiacinamide, also known as nicotinamid or nicovit, 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. Niacinamide is a strong basic compound (based on its pKa). Niacinamide exists in all living species, ranging from bacteria to humans. niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate through the action of the enzyme nicotinamide phosphoribosyltransferase. In humans, niacinamide is involved in the metabolic disorder called the nad+ signalling pathway (cancer). Niacinamide is an odorless tasting compound. Outside of the human body, Niacinamide is found, on average, in the highest concentration within a few different foods, such as common sages, milk (cow), and cocoa beans and in a lower concentration in common pea and beers. Niacinamide has also been detected, but not quantified in, several different foods, such as pineappple sages, boysenberries, cashew nuts, macadamia nut (m. tetraphylla), and sweet marjorams. This could make niacinamide a potential biomarker for the consumption of these foods. Niacinamide is a potentially toxic compound. A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.
CAS Number98-92-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 Parents
Substituents
  • Nicotinamide
  • Heteroaromatic compound
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0kor-9600000000-2b1c5667d92bc1b80b362014-09-20View Spectrum
GC-MSNicotinamide, 1 TMS, GC-MS Spectrumsplash10-004i-0900000000-acb6a21304b0c09c8472Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004r-0900000000-ce86dcff0153b66dd538Spectrum
GC-MSNicotinamide, 1 TMS, GC-MS Spectrumsplash10-004i-9500000000-790385e574240b8d39deSpectrum
GC-MSNicotinamide, 2 TMS, GC-MS Spectrumsplash10-0udi-2910000000-d760b65bb76d6464038eSpectrum
GC-MSNicotinamide, 1 TMS, GC-MS Spectrumsplash10-004i-4900000000-47c6f72d1bb5465c1376Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-0kor-9800000000-1809e537780b814af0c9Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-0kor-9800000000-c4a5ff5285417499eff8Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-0e84a60cc2a2d44704f4Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-acb6a21304b0c09c8472Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004r-0900000000-ce86dcff0153b66dd538Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004i-9500000000-790385e574240b8d39deSpectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-0udi-2910000000-d760b65bb76d6464038eSpectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-47c6f72d1bb5465c1376Spectrum
GC-MSNicotinamide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-23a567506bfbc259e77cSpectrum
Predicted GC-MSNicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-8900000000-931c139355be3ef594f2Spectrum
Predicted GC-MSNicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-2900000000-72a7c92eb2667f5b6c3f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kor-9800000000-89d56b6cb7e033699d242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-eed71abbb10ba926c13d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-3900000000-0c62aa6aba6e23b6c1952012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9100000000-4357a8833611d1756c592012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-c9685717817d0081fe6d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f6d71a6c467f84ddd6ab2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-62c4bd312efbfa37d1a12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-05714b528dc84942b9db2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-edb6a77c0dfdcbdacc5d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-eed71abbb10ba926c13d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-3900000000-0c62aa6aba6e23b6c1952017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-4357a8833611d1756c592017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-c9685717817d0081fe6d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-960acce7ead55399b5db2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c7ec333d35eb740520a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9600000000-466f98885e2efba735752015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9200000000-6ef8d7e5edcdd0b027582015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-f38177aa475e589410882015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-6a883d82fcd7c450f6ce2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-882d0c59d946a5087b9f2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).