nicotinamide (CHEBI:17154)

ChEBI > Main

CHEBI:17154 - nicotinamide

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	nicotinamide

ChEBI ID	CHEBI:17154

Definition	A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44258, CHEBI:7556, CHEBI:14645, CHEBI:25521

Supplier Information	ChemicalBook:CB8439347, eMolecules:524521, ZINC000000895261

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__396188041262468__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__396188041262468__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17154","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__396188041262468__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"396188041262468","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__396188041262468__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

Marvin 10180713443D

starting HoverWatcher_5

Time for openFile(

Marvin 10180713443D

15 15 0 0 1 0 999 V2000

-2.1376 1.1964 0.1234 C 0 0 0 0 0 0 0 0 0 6 0 0

-2.1864 -0.2078 0.1471 C 0 0 0 0 0 0 0 0 0 5 0 0

-0.9762 -0.9258 0.1433 C 0 0 0 0 0 0 0 0 0 4 0 0

0.2409 1.1546 0.0875 C 0 0 0 0 0 0 0 0 0 2 0 0

-0.9377 1.8242 0.0967 N 0 0 0 0 0 0 0 0 0 1 0 0

0.2761 -0.2629 0.1061 C 0 0 0 0 0 0 0 0 0 3 0 0

1.4741 -0.9653 0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5863 -2.0791 0.5707 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5285 -0.4944 -0.4818 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.9947 1.7508 0.1257 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0845 -0.6955 0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0290 -1.9482 0.1542 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0955 1.7154 0.0733 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3284 -0.9777 -0.4810 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4936 0.3375 -0.9077 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 4 0 0 0 0

3 2 4 0 0 0 0

1 5 4 0 0 0 0

5 4 4 0 0 0 0

4 6 4 0 0 0 0

3 6 4 0 0 0 0

6 7 1 0 0 0 0

7 9 1 0 0 0 0

7 8 2 0 0 0 0

1 10 1 0 0 0 0

2 11 1 0 0 0 0

3 12 1 0 0 0 0

4 13 1 0 0 0 0

9 14 1 0 0 0 0

9 15 1 0 0 0 0

M END): 32 ms

reading 15 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

15 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Wikipedia	License
Nicotinamide (INN, BAN UK) or niacinamide (USAN US) is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used orally (swallowed by mouth) to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causing skin flushing. As a cream, it is used to treat acne, and has been observed in clinical studies to improve the appearance of aging skin by reducing hyperpigmentation and redness. It is a water-soluble vitamin. Side effects are minimal. At high doses, liver problems may occur. Normal amounts are safe for use during pregnancy. Nicotinamide is in the vitamin B family of medications, specifically the vitamin B3 complex. It is an amide of nicotinic acid. Foods that contain nicotinamide include yeast, meat, milk, and green vegetables. Nicotinamide was discovered between 1935 and 1937. It is on the World Health Organization's List of Essential Medicines. Nicotinamide is available as a generic medication and over the counter. Commercially, nicotinamide is made from either nicotinic acid (niacin) or nicotinonitrile. In some countries, grains have nicotinamide added to them.
Read full article at Wikipedia

Formula

C6H6N2O

Net Charge

Average Mass

122.12472

Monoisotopic Mass

122.04801

InChI

InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

InChIKey

DFPAKSUCGFBDDF-UHFFFAOYSA-N

SMILES

NC(=O)c1cccnc1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in breast milk (ENVO:02000031). See: PubMed
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid ) Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). Sir2 inhibitor An EC 3.5.1.98 (histone deacetylase) inhibitor that interferes with the action of Sir2. EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor An EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of a NAD+ ADP-ribosyltransferase (EC 2.4.2.30). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via B vitamin )

Application(s):	neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. anti-inflammatory agent Any compound that has anti-inflammatory effects. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	nicotinamide (CHEBI:17154) has functional parent nicotinic acid (CHEBI:15940) nicotinamide (CHEBI:17154) has role Escherichia coli metabolite (CHEBI:76971) nicotinamide (CHEBI:17154) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) nicotinamide (CHEBI:17154) has role anti-inflammatory agent (CHEBI:67079) nicotinamide (CHEBI:17154) has role antioxidant (CHEBI:22586) nicotinamide (CHEBI:17154) has role cofactor (CHEBI:23357) nicotinamide (CHEBI:17154) has role EC 2.4.2.30 (NAD⁺ ADP-ribosyltransferase) inhibitor (CHEBI:62913) nicotinamide (CHEBI:17154) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115) nicotinamide (CHEBI:17154) has role geroprotector (CHEBI:176497) nicotinamide (CHEBI:17154) has role human urinary metabolite (CHEBI:84087) nicotinamide (CHEBI:17154) has role metabolite (CHEBI:25212) nicotinamide (CHEBI:17154) has role mouse metabolite (CHEBI:75771) nicotinamide (CHEBI:17154) has role neuroprotective agent (CHEBI:63726) nicotinamide (CHEBI:17154) has role Sir2 inhibitor (CHEBI:71181) nicotinamide (CHEBI:17154) is a pyridine alkaloid (CHEBI:26416) nicotinamide (CHEBI:17154) is a pyridinecarboxamide (CHEBI:25529) nicotinamide (CHEBI:17154) is a vitamin B₃ (CHEBI:176839)

Incoming	1-[(2-chlorophenyl)methyl]-2-oxo-6-(trifluoromethyl)-3-pyridinecarboxamide (CHEBI:114321) has functional parent nicotinamide (CHEBI:17154) 1-[[oxo(3-pyridinyl)methyl]amino]-3-(4-propan-2-ylphenyl)thiourea (CHEBI:120875) has functional parent nicotinamide (CHEBI:17154) 1-methylnicotinamide (CHEBI:16797) has functional parent nicotinamide (CHEBI:17154) 2-(2,4-dimethylanilino)-N-(thiophen-2-ylmethyl)-3-pyridinecarboxamide (CHEBI:104887) has functional parent nicotinamide (CHEBI:17154) 2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-3-pyridinecarboxamide (CHEBI:91424) has functional parent nicotinamide (CHEBI:17154) 2-(4-chloro-2-methylanilino)-3-pyridinecarboxamide (CHEBI:108168) has functional parent nicotinamide (CHEBI:17154) 2-(methylthio)nicotinamide (CHEBI:228655) has functional parent nicotinamide (CHEBI:17154) 2-methylnicotinamide (CHEBI:68440) has functional parent nicotinamide (CHEBI:17154) 2-oxo-N-(2-thiazolyl)-1H-pyridine-3-carboxamide (CHEBI:120549) has functional parent nicotinamide (CHEBI:17154) 5-bromo-N-(4-methyl-2-thiazolyl)-3-pyridinecarboxamide (CHEBI:122191) has functional parent nicotinamide (CHEBI:17154) 5-bromo-N-[(2-pyridinylamino)-sulfanylidenemethyl]-3-pyridinecarboxamide (CHEBI:120534) has functional parent nicotinamide (CHEBI:17154) 5-bromo-N-[(5-nitro-2-thiophenyl)methylideneamino]-3-pyridinecarboxamide (CHEBI:104973) has functional parent nicotinamide (CHEBI:17154) 5-bromo-N-[[(3-methyl-2-pyridinyl)amino]-sulfanylidenemethyl]-3-pyridinecarboxamide (CHEBI:93987) has functional parent nicotinamide (CHEBI:17154) 5-bromo-N-[[(4-methyl-2-pyridinyl)amino]-sulfanylidenemethyl]-3-pyridinecarboxamide (CHEBI:116399) has functional parent nicotinamide (CHEBI:17154) 5-hydroxy-N-[2-[[(5-hydroxy-3-pyridinyl)-oxomethyl]amino]propyl]-3-pyridinecarboxamide (CHEBI:104006) has functional parent nicotinamide (CHEBI:17154) 6-methoxy-4-(trifluoromethyl)nicotinamide (CHEBI:183364) has functional parent nicotinamide (CHEBI:17154) 6-methyl-N-(2-pyridinylmethylideneamino)-3-pyridinecarboxamide (CHEBI:107154) has functional parent nicotinamide (CHEBI:17154) 6-methyl-N-[(2-methyl-3-phenylprop-2-enylidene)amino]-3-pyridinecarboxamide (CHEBI:105981) has functional parent nicotinamide (CHEBI:17154) 6-Methylnicotinamide (CHEBI:88954) has functional parent nicotinamide (CHEBI:17154) N-glycosylnicotinamide (CHEBI:25526) has functional parent nicotinamide (CHEBI:17154) N-methylnicotinamide (CHEBI:64399) has functional parent nicotinamide (CHEBI:17154) N-{5-[4-(4-methylpiperazin-1-yl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}nicotinamide (CHEBI:39634) has functional parent nicotinamide (CHEBI:17154) acetic acid 2-[[oxo(3-pyridinyl)methyl]amino]ethyl ester (CHEBI:92313) has functional parent nicotinamide (CHEBI:17154) flumetnicam (CHEBI:231554) has functional parent nicotinamide (CHEBI:17154) Himeic acid G (CHEBI:211171) has functional parent nicotinamide (CHEBI:17154) hydroxymethylnicotinamide (CHEBI:134775) has functional parent nicotinamide (CHEBI:17154) Myxochelin N (CHEBI:222142) has functional parent nicotinamide (CHEBI:17154) Myxochelin O (CHEBI:222138) has functional parent nicotinamide (CHEBI:17154) N'3-(3,4,5-trimethoxybenzylidene)pyridine-3-carbohydrazide (CHEBI:183773) has functional parent nicotinamide (CHEBI:17154) N,N-Dihexylnicotinamide (CHEBI:189375) has functional parent nicotinamide (CHEBI:17154) N-(1-adamantyl)-5-hydroxy-3-pyridinecarboxamide (CHEBI:104155) has functional parent nicotinamide (CHEBI:17154) N-(2-fluorophenyl)-2-methyl-6-(trifluoromethyl)nicotinamide (CHEBI:189499) has functional parent nicotinamide (CHEBI:17154) N-[(2-methyl-3-phenylprop-2-enylidene)amino]-3-pyridinecarboxamide (CHEBI:105703) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[2-(1-piperidinyl)ethylamino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:100861) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118385) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118398) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6R)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118597) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[2-(1-piperidinyl)ethylamino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:101057) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118291) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3R,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118425) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[2-(1-piperidinyl)ethylamino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:99262) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118445) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6R)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118736) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[2-(1-piperidinyl)ethylamino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:100693) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:124890) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:124301) has functional parent nicotinamide (CHEBI:17154) N-[(2R,3S,6S)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118714) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[2-(1-piperidinyl)ethylamino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:102693) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:124865) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:124262) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6R)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118717) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6S)-2-(hydroxymethyl)-6-[2-oxo-2-(2-piperidin-1-ylethylamino)ethyl]-3,6-dihydro-2H-pyran-3-yl]pyridine-3-carboxamide (CHEBI:98207) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:124899) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:124859) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3R,6S)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118547) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6R)-2-(hydroxymethyl)-6-[2-oxo-2-(2-piperidin-1-ylethylamino)ethyl]-3,6-dihydro-2H-pyran-3-yl]pyridine-3-carboxamide (CHEBI:98467) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118474) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6R)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118386) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6R)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118573) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6S)-2-(hydroxymethyl)-6-[2-oxo-2-(2-piperidin-1-ylethylamino)ethyl]-3,6-dihydro-2H-pyran-3-yl]pyridine-3-carboxamide (CHEBI:97296) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118300) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6S)-2-(hydroxymethyl)-6-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118418) has functional parent nicotinamide (CHEBI:17154) N-[(2S,3S,6S)-6-[2-[(3,4-dichlorophenyl)methylamino]-2-oxoethyl]-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]-3-pyridinecarboxamide (CHEBI:118748) has functional parent nicotinamide (CHEBI:17154) N-[(3,3-dimethyl-5-oxocyclohexylidene)amino]-3-pyridinecarboxamide (CHEBI:108969) has functional parent nicotinamide (CHEBI:17154) N-[1,1,1,3,3,3-hexafluoro-2-(2-pyridinylmethylamino)propan-2-yl]-3-pyridinecarboxamide (CHEBI:94517) has functional parent nicotinamide (CHEBI:17154) N-[2-[2-[2-[[oxo(3-pyridinyl)methyl]amino]ethoxy]ethoxy]ethyl]-3-pyridinecarboxamide (CHEBI:114454) has functional parent nicotinamide (CHEBI:17154) N-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]-3-pyridinecarboxamide (CHEBI:107956) has functional parent nicotinamide (CHEBI:17154) N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-3-pyridinecarboxamide (CHEBI:105309) has functional parent nicotinamide (CHEBI:17154) N-[6-(1-oxopentylamino)-3-pyridinyl]-3-pyridinecarboxamide (CHEBI:121625) has functional parent nicotinamide (CHEBI:17154) N-[[(2R,3R)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95855) has functional parent nicotinamide (CHEBI:17154) N-[[(2R,3R)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96617) has functional parent nicotinamide (CHEBI:17154) N-[[(2R,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95777) has functional parent nicotinamide (CHEBI:17154) N-[[(2R,3S)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95921) has functional parent nicotinamide (CHEBI:17154) N-[[(2S,3R)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96139) has functional parent nicotinamide (CHEBI:17154) N-[[(2S,3R)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95864) has functional parent nicotinamide (CHEBI:17154) N-[[(2S,3S)-5-[(2R)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96344) has functional parent nicotinamide (CHEBI:17154) N-[[(2S,3S)-5-[(2S)-1-hydroxypropan-2-yl]-3-methyl-8-(3-methylbut-1-ynyl)-6-oxo-3,4-dihydro-2H-pyrido[2,3-b][1,5]oxazocin-2-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95684) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5R)-2-[(2R)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95995) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5R)-2-[(2S)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95600) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5R)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2R)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95717) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5R)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2S)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95552) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5S)-2-[(2R)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95670) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5S)-2-[(2S)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96381) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5S)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2R)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96468) has functional parent nicotinamide (CHEBI:17154) N-[[(4R,5S)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2S)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95700) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5R)-2-[(2R)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95969) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5R)-2-[(2S)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96539) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5R)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2R)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95912) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5R)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2S)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:116657) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5R)-8-bromo-2-[(2S)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:110094) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5S)-2-[(2R)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:95974) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5S)-2-[(2S)-1-hydroxypropan-2-yl]-8-(2-methoxyphenyl)-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96360) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5S)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2R)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96511) has functional parent nicotinamide (CHEBI:17154) N-[[(4S,5S)-8-[2-(1-hydroxycyclopentyl)ethynyl]-2-[(2S)-1-hydroxypropan-2-yl]-4-methyl-1,1-dioxo-4,5-dihydro-3H-6,1$l^{6},2-benzoxathiazocin-5-yl]methyl]-N-methyl-3-pyridinecarboxamide (CHEBI:96067) has functional parent nicotinamide (CHEBI:17154) N-[[3-methoxy-4-[2-(4-methylanilino)-2-oxoethoxy]phenyl]methylideneamino]-3-pyridinecarboxamide (CHEBI:116480) has functional parent nicotinamide (CHEBI:17154) N-[[5-(4-nitrophenyl)-2-furanyl]methylideneamino]-3-pyridinecarboxamide (CHEBI:116670) has functional parent nicotinamide (CHEBI:17154) N-methyl-N-[5-(3-pyridinyl)-1,3,4-thiadiazol-2-yl]-3-pyridinecarboxamide (CHEBI:115102) has functional parent nicotinamide (CHEBI:17154) nicorandil (CHEBI:31905) has functional parent nicotinamide (CHEBI:17154) Nicoxamat (CHEBI:173404) has functional parent nicotinamide (CHEBI:17154) nikethamide (CHEBI:134814) has functional parent nicotinamide (CHEBI:17154) Penipyridone A (CHEBI:227809) has functional parent nicotinamide (CHEBI:17154) Penipyridone C (CHEBI:227819) has functional parent nicotinamide (CHEBI:17154) Penipyridone D (CHEBI:227822) has functional parent nicotinamide (CHEBI:17154) Penipyridone F (CHEBI:227832) has functional parent nicotinamide (CHEBI:17154) Pestalamide C (CHEBI:197575) has functional parent nicotinamide (CHEBI:17154) Pestalamide D (CHEBI:215530) has functional parent nicotinamide (CHEBI:17154) Poronitin B (CHEBI:202835) has functional parent nicotinamide (CHEBI:17154)

IUPAC Name

pyridine-3-carboxamide

INNs	Sources
nicotinamida	WHO MedNet
nicotinamide	WHO MedNet
nicotinamide	WHO MedNet
nicotinamidum	WHO MedNet

Synonyms

Sources

3-carbamoylpyridine

ChemIDplus

3-pyridinecarboxamide

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

β-pyridinecarboxamide

ChemIDplus

β-pyridinecarboxamide

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

m-(aminocarbonyl)pyridine

ChemIDplus

niacin

ChEBI

Niacinamide

KEGG COMPOUND

niamide

ChemIDplus

Nicotinamid Deutsch

ChEBI

nicotinamide

UniProt

nicotine acid amide

ChemIDplus

nicotine amide

ChemIDplus

nicotinic acid amide

ChemIDplus

nicotinic amide

ChemIDplus

Nicotinsäureamid Deutsch

ChEBI

nicotylamide

ChemIDplus

Nikotinamid Deutsch

ChemIDplus

Nikotinsäureamid Deutsch

ChEBI

pyridine-3-carboxylic acid amide

ChemIDplus

vitamin B₃

Note: (2015-01-13) Note that the term 'vitamin B₃' has also been used as a synonym for nicotinic acid, as well as for other molecules that exhibit the biological activity of nicotinic acid.

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

Vitamin PP

Note: (2015-01-13) Note that the term 'vitamin PP' has also been used as a synonym for nicotinic acid.

KEGG COMPOUND

Manual Xrefs	Databases
1906	DrugCentral
C00000209	KNApSAcK
C00153	KEGG COMPOUND
D00036	KEGG DRUG
DB02701	DrugBank
FDB012485	FooDB
HMDB0001406	HMDB
LSM-5428	LINCS
NCA	PDBeChem
NIACINAMIDE	MetaCyc
Nicotinamide	Wikipedia
US2904552	Patent
US2993051	Patent
View more database links

Registry Numbers	Types	Sources
3336	Gmelin Registry Number	Gmelin
383619	Reaxys Registry Number	Reaxys
98-92-0	CAS Registry Number	ChemIDplus
98-92-0	CAS Registry Number	NIST Chemistry WebBook

Citations

Last Modified

10 June 2024

General Comment
2015-01-13	Note that the term 'niacin' has also been used as a synonym for nicotinic acid.

CHEBI:17154 - nicotinamide

ChEBI is part of the ELIXIR infrastructure