You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:30 UTC
HMDB IDHMDB0001406
Secondary Accession Numbers
  • HMDB01406
Metabolite Identification
Common NameNiacinamide
DescriptionNiacinamide, also known as nicotinamide (NAM), is a form of vitamin B3 found in food and used as a dietary supplement and medication. Niacinamide 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. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. The structure of nicotinamide consists of a pyridine ring to which a primary amide group is attached in the meta position. It is an amide of nicotinic acid. As an aromatic compound, it undergoes electrophilic substitution reactions and transformations of its two functional groups. Niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate by 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, cow milk, and cocoa beans and in a lower concentration in common pea. Niacinamide has also been detected, but not quantified in several different foods, such as yardlong beans, roselles, apples, oyster mushrooms, and swiss chards. Niacinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables. It is commonly added to cereals and other foods. Many multivitamins contain 20–30 mg of vitamin B3 and it is also available in higher doses. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake.
Structure
Data?1582752199
Synonyms
ValueSource
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
NiacinamideChEBI
Chemical FormulaC6H6N2O
Average Molecular Weight122.1246
Monoisotopic Molecular Weight122.048012824
IUPAC Namepyridine-3-carboxamide
Traditional Namenicotinamide
CAS Registry Number98-92-0
SMILES
NC(=O)C1=CC=CN=C1
InChI Identifier
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
InChI KeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
Chemical Taxonomy
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:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mL at 25 °CNot Available
LogP-0.37HANSCH,C ET AL. (1995)
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M+H]+ExperimentalBaker131.66730932474
AllCCS[M+H]+ExperimentalNot Available126.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000481
DarkChem[M+H]+PredictedNot Available124.54131661259
DarkChem[M-H]-PredictedNot Available118.21831661259
AllCCS[M+H]+PredictedNot Available125.58432859911
AllCCS[M-H]-PredictedNot Available121.53832859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-0900000000-acb6a21304b0c09c84722014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd5382014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9500000000-790385e574240b8d39de2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2910000000-d760b65bb76d6464038e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-4900000000-47c6f72d1bb5465c13762014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-1809e537780b814af0c92017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kor-9800000000-c4a5ff5285417499eff82017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-0e84a60cc2a2d44704f42017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-acb6a21304b0c09c84722017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-0900000000-ce86dcff0153b66dd5382017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9500000000-790385e574240b8d39de2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2910000000-d760b65bb76d6464038e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-4900000000-47c6f72d1bb5465c13762017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-23a567506bfbc259e77c2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-8900000000-931c139355be3ef594f22016-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kor-9600000000-2b1c5667d92bc1b80b362014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-2900000000-72a7c92eb2667f5b6c3f2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-6486d230a4a2fd4bab0e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kor-9800000000-89d56b6cb7e033699d242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-eed71abbb10ba926c13d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-3900000000-0c62aa6aba6e23b6c1952012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9100000000-4357a8833611d1756c592012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-c9685717817d0081fe6d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a782012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f6d71a6c467f84ddd6ab2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-62c4bd312efbfa37d1a12012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-05714b528dc84942b9db2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9100000000-edb6a77c0dfdcbdacc5d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-eed71abbb10ba926c13d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-3900000000-0c62aa6aba6e23b6c1952017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-4357a8833611d1756c592017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-c9685717817d0081fe6d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fc0-9000000000-ec0ccca306f38cf72a782017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-960acce7ead55399b5db2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c7ec333d35eb740520a2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-9600000000-466f98885e2efba735752015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9200000000-6ef8d7e5edcdd0b027582015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-f38177aa475e589410882015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-9800000000-6a883d82fcd7c450f6ce2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-882d0c59d946a5087b9f2015-05-27View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (predicted)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Breast Milk
  • Feces
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Neuron
  • Pancreas
  • Placenta
  • Prostate
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.03 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.44 +/- 0.0054 uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified5.3 +/- 3.3 uMAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.30 +/- 0.51 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.29 +/- 0.24 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedasymptomatic diverticulosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB02701
Phenol Explorer Compound IDNot Available
FooDB IDFDB012485
KNApSAcK IDC00000209
Chemspider ID911
KEGG Compound IDC00153
BioCyc IDNIACINAMIDE
BiGG ID34058
Wikipedia LinkNicotinamide
METLIN ID1497
PubChem Compound936
PDB IDNot Available
ChEBI ID17154
Food Biomarker OntologyNot Available
VMH IDNCAM
MarkerDB IDNot Available
References
Synthesis ReferenceGalat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Draelos ZD, Ertel K, Berge C: Niacinamide-containing facial moisturizer improves skin barrier and benefits subjects with rosacea. Cutis. 2005 Aug;76(2):135-41. [PubMed:16209160 ]
  2. Soma Y, Kashima M, Imaizumi A, Takahama H, Kawakami T, Mizoguchi M: Moisturizing effects of topical nicotinamide on atopic dry skin. Int J Dermatol. 2005 Mar;44(3):197-202. [PubMed:15807725 ]
  3. Authors unspecified: Final report of the safety assessment of niacinamide and niacin. Int J Toxicol. 2005;24 Suppl 5:1-31. [PubMed:16596767 ]
  4. Draelos ZD, Matsubara A, Smiles K: The effect of 2% niacinamide on facial sebum production. J Cosmet Laser Ther. 2006 Jun;8(2):96-101. [PubMed:16766489 ]
  5. Schulpis K, Spiropoulos A, Gavrili S, Karikas G, Grigori C, Vlachos G, Papassotiriou I: Maternal - neonatal folate and vitamin B12 serum concentrations in Greeks and in Albanian immigrants. J Hum Nutr Diet. 2004 Oct;17(5):443-8. [PubMed:15357698 ]
  6. Yang L, Yao Y, Shi Y, Wang X, Shi J: [Expression of nicotinamide edenine dinucleotide dehydrogenase gene in placenta of patients with pregnancy induced hypertension]. Zhonghua Fu Chan Ke Za Zhi. 2002 Nov;37(11):660-2. [PubMed:12487919 ]
  7. Sonee M, Martens JR, Mukherjee SK: Nicotinamide protects HCN2 cells from the free radical generating toxin, tertiary butylhydroperoxide (t-BuOOH). Neurotox Res. 2002 Nov-Dec;4(7-8):595-599. [PubMed:12709297 ]
  8. Bayraktar F, Dereli D, Ozgen AG, Yilmaz C: Plasma homocysteine levels in polycystic ovary syndrome and congenital adrenal hyperplasia. Endocr J. 2004 Dec;51(6):601-8. [PubMed:15644580 ]
  9. Sonee M, Martens JR, Evers MR, Mukherjee SK: The effect of tertiary butylhydroperoxide and nicotinamide on human cortical neurons. Neurotoxicology. 2003 Jun;24(3):443-8. [PubMed:12782109 ]
  10. Anisimov AG, Bolotnikov IA: [Nicotinamide decreases DNA destabilization in K562 cells treated with AlF(-4)]. Tsitologiia. 1997;39(9):822-8. [PubMed:9518388 ]
  11. Matuoka K, Chen KY, Takenawa T: Rapid reversion of aging phenotypes by nicotinamide through possible modulation of histone acetylation. Cell Mol Life Sci. 2001 Dec;58(14):2108-16. [PubMed:11814060 ]
  12. Bartalena L, Tanda ML, Piantanida E, Lai A: Oxidative stress and Graves' ophthalmopathy: in vitro studies and therapeutic implications. Biofactors. 2003;19(3-4):155-63. [PubMed:14757966 ]
  13. Bissett DL, Oblong JE, Berge CA: Niacinamide: A B vitamin that improves aging facial skin appearance. Dermatol Surg. 2005 Jul;31(7 Pt 2):860-5; discussion 865. [PubMed:16029679 ]
  14. Baeza N, Moriscot C, Figarella C, Guy-Crotte O, Vialettes B: Reg protein: a potential beta-cell-specific growth factor? Diabetes Metab. 1996 Jul;22(4):229-34. [PubMed:8767167 ]
  15. Hoskin PJ, Rojas AM, Phillips H, Saunders MI: Acute and late morbidity in the treatment of advanced bladder carcinoma with accelerated radiotherapy, carbogen, and nicotinamide. Cancer. 2005 Jun 1;103(11):2287-97. [PubMed:15834926 ]
  16. Rembold CM: Combination therapy of dyslipidemia in non-insulin-dependent diabetes mellitus and the metabolic syndrome. Curr Diab Rep. 2004 Oct;4(5):330-4. [PubMed:15461896 ]
  17. Kawasaki E, Abiru N, Eguchi K: Prevention of type 1 diabetes: from the view point of beta cell damage. Diabetes Res Clin Pract. 2004 Dec;66 Suppl 1:S27-32. [PubMed:15563975 ]
  18. Rybak ME, Pfeiffer CM: Clinical analysis of vitamin B(6): determination of pyridoxal 5'-phosphate and 4-pyridoxic acid in human serum by reversed-phase high-performance liquid chromatography with chlorite postcolumn derivatization. Anal Biochem. 2004 Oct 15;333(2):336-44. [PubMed:15450810 ]
  19. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  20. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  21. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 37 proteins in total.

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the N-methylation of nicotinamide and other pyridines to form pyridinium ions. This activity is important for biotransformation of many drugs and xenobiotic compounds.
Gene Name:
NNMT
Uniprot ID:
P40261
Molecular weight:
29573.705
Reactions
S-Adenosylmethionine + Niacinamide → S-Adenosylhomocysteine + 1-Methylnicotinamidedetails
S-Adenosylmethionine + Niacinamide + Hydrogen Ion → S-Adenosylhomocysteine + 1-Methylnicotinamidedetails
General function:
Involved in NAD+ ADP-ribosyltransferase activity
Specific function:
Poly-ADP-ribosyltransferase involved in various processes such as Wnt signaling pathway, telomere length and vesicle trafficking. Acts as an activator of the Wnt signaling pathway by mediating poly-ADP-ribosylation of AXIN1 and AXIN2, 2 key components of the beta-catenin destruction complex: poly-ADP-ribosylated target proteins are recognized by RNF146, which mediates their ubiquitination and subsequent degradation. Also mediates poly-ADP-ribosylation of BLZF1 and CASC3, followed by recruitment of RNF146 and subsequent ubiquitination. Mediates poly-ADP-ribosylation of TERF1, thereby contributing to the regulation of telomere length. May also regulate vesicle trafficking and modulate the subcellular distribution of SLC2A4/GLUT4-vesicles.
Gene Name:
TNKS2
Uniprot ID:
Q9H2K2
Molecular weight:
126916.895
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor → Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
General function:
Involved in zinc ion binding
Specific function:
NAD-dependent protein deacetylase. Has deacetylase activity towards histone H3K9Ac and H3K56Ac. Modulates acetylation of histone H3 in telomeric chromatin during the S-phase of the cell cycle. Deacetylates histone H3K9Ac at NF-kappa-B target promoters and may down-regulate the expression of a subset of NF-kappa-B target genes. Acts as a corepressor of the transcription factor HIF1A to control the expression of multiple glycolytic genes to regulate glucose homeostasis. Required for genomic stability. Regulates the production of TNF protein. Has a role in the regulation of life span (By similarity). Deacetylation of nucleosomes interferes with RELA binding to target DNA. May be required for the association of WRN with telomeres during S-phase and for normal telomere maintenance. Required for genomic stability. Required for normal IGF1 serum levels and normal glucose homeostasis. Modulates cellular senescence and apoptosis. On DNA damage, promotes DNA end resection via deacetylation of RBBP8. Has very weak deacetylase activity and can bind NAD(+) in the absence of acetylated substrate.
Gene Name:
SIRT6
Uniprot ID:
Q8N6T7
Molecular weight:
36064.295
Reactions
NAD + an acetylprotein → Niacinamide + O-acetyl-ADP-ribose + a proteindetails
General function:
Involved in NAD+ ADP-ribosyltransferase activity
Specific function:
Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This modification follows DNA damages and appears as an obligatory step in a detection/signaling pathway leading to the reparation of DNA strand breaks. May link the DNA damage surveillance network to the mitotic fidelity checkpoint. Negatively influences the G1/S cell cycle progression without interfering with centrosome duplication. Binds DNA. May be involved in the regulation of PRC2 and PRC3 complex-dependent gene silencing.
Gene Name:
PARP3
Uniprot ID:
Q9Y6F1
Molecular weight:
60845.685
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor → Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
General function:
Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
Specific function:
Not Available
Gene Name:
ART3
Uniprot ID:
Q13508
Molecular weight:
43922.97
Reactions
NAD + protein-L-arginine → Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine → Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
General function:
Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
Specific function:
Not Available
Gene Name:
ART5
Uniprot ID:
Q96L15
Molecular weight:
32053.48
Reactions
NAD + protein-L-arginine → Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine → Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
General function:
Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
Specific function:
Has ADP-ribosyltransferase activity toward GLP1R.
Gene Name:
ART1
Uniprot ID:
P52961
Molecular weight:
36334.32
Reactions
NAD + protein-L-arginine → Niacinamide + N(omega)-(ADP-D-ribosyl)-protein-L-argininedetails
NADP + protein-L-arginine → Niacinamide + N(omega)-((2'-phospho-ADP)-D-ribosyl)-protein-L-argininedetails
General function:
Involved in NAD+ ADP-ribosyltransferase activity
Specific function:
Poly-ADP-ribosyltransferase involved in various processes such as Wnt signaling pathway, telomere length and vesicle trafficking. Acts as an activator of the Wnt signaling pathway by mediating poly-ADP-ribosylation (PARsylation) of AXIN1 and AXIN2, 2 key components of the beta-catenin destruction complex: poly-ADP-ribosylated target proteins are recognized by RNF146, which mediates their ubiquitination and subsequent degradation. Also mediates PARsylation of BLZF1 and CASC3, followed by recruitment of RNF146 and subsequent ubiquitination. Mediates PARsylation of TERF1, thereby contributing to the regulation of telomere length. Involved in centrosome maturation during prometaphase by mediating PARsylation of HEPACAM2/MIKI. May also regulate vesicle trafficking and modulate the subcellular distribution of SLC2A4/GLUT4-vesicles. May be involved in spindle pole assembly through PARsylation of NUMA1.
Gene Name:
TNKS
Uniprot ID:
O95271
Molecular weight:
142038.18
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor → Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
General function:
Involved in DNA binding
Specific function:
Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This modification follows DNA damages and appears as an obligatory step in a detection/signaling pathway leading to the reparation of DNA strand breaks. Mediates the poly(ADP-ribosyl)ation of APLF and CHFR. Positively regulates the transcription of MTUS1 and negatively regulates the transcription of MTUS2/TIP150. With EEF1A1 and TXK, forms a complex that acts as a T-helper 1 (Th1) cell-specific transcription factor and binds the promoter of IFN-gamma to directly regulate its transcription, and is thus involved importantly in Th1 cytokine production.
Gene Name:
PARP1
Uniprot ID:
P09874
Molecular weight:
113082.945
Reactions
NAD + (ADP-D-ribosyl)(n)-acceptor → Niacinamide + (ADP-D-ribosyl)(n+1)-acceptordetails
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in NAD+ nucleosidase activity
Specific function:
Synthesizes cyclic ADP-ribose, a second messenger that elicits calcium release from intracellular stores. May be involved in pre-B-cell growth.
Gene Name:
BST1
Uniprot ID:
Q10588
Molecular weight:
35723.545
Reactions
NAD + Water → Adenosine diphosphate ribose + Niacinamidedetails
NADP + Water → Niacinamide + (E)-3-(2,3-Dihydroxyphenyl)-2-propenoic aciddetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Only showing the first 10 proteins. There are 37 proteins in total.