CHEBI:15940 - nicotinic acid

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ChEBI Name nicotinic acid
ChEBI ID CHEBI:15940
Definition A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44319, CHEBI:7559, CHEBI:25538
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Formula C6H5NO2
Net Charge 0
Average Mass 123.10944
Monoisotopic Mass 123.03203
InChI InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChIKey PVNIIMVLHYAWGP-UHFFFAOYSA-N
SMILES OC(=O)c1cccnc1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Bacillus subtilis (NCBI:txid1423) of strain 29784 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Cordyceps sinensis (NCBI:txid72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Homo sapiens (NCBI:txid9606) Found in cerebrospinal fluid (UBERON:0001359). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) Found in faeces (UBERON:0001988). See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606) From MetaboLights See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
EC 3.5.1.19 (nicotinamidase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of nicotinamidase (EC 3.5.1.19).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
water-soluble vitamin

(via B vitamin )
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
antidote
Any protective agent counteracting or neutralizing the action of poisons.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
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 nicotinic acid (CHEBI:15940) has role Escherichia coli metabolite (CHEBI:76971)
nicotinic acid (CHEBI:15940) has role antidote (CHEBI:50247)
nicotinic acid (CHEBI:15940) has role antilipemic drug (CHEBI:35679)
nicotinic acid (CHEBI:15940) has role EC 3.5.1.19 (nicotinamidase) inhibitor (CHEBI:84264)
nicotinic acid (CHEBI:15940) has role human urinary metabolite (CHEBI:84087)
nicotinic acid (CHEBI:15940) has role metabolite (CHEBI:25212)
nicotinic acid (CHEBI:15940) has role mouse metabolite (CHEBI:75771)
nicotinic acid (CHEBI:15940) has role plant metabolite (CHEBI:76924)
nicotinic acid (CHEBI:15940) has role vasodilator agent (CHEBI:35620)
nicotinic acid (CHEBI:15940) is a pyridine alkaloid (CHEBI:26416)
nicotinic acid (CHEBI:15940) is a pyridinemonocarboxylic acid (CHEBI:26420)
nicotinic acid (CHEBI:15940) is a vitamin B3 (CHEBI:176839)
nicotinic acid (CHEBI:15940) is conjugate acid of nicotinate (CHEBI:32544)
Incoming 1,4,5,6-tetrahydro-6-oxonicotinic acid (CHEBI:16453) has functional parent nicotinic acid (CHEBI:15940)
2,6-dihydroxynicotinic acid (CHEBI:49087) has functional parent nicotinic acid (CHEBI:15940)
2-aminonicotinic acid (CHEBI:68572) has functional parent nicotinic acid (CHEBI:15940)
4-aminonicotinic acid (CHEBI:68577) has functional parent nicotinic acid (CHEBI:15940)
4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (CHEBI:17693) has functional parent nicotinic acid (CHEBI:15940)
5-aminonicotinic acid (CHEBI:68578) has functional parent nicotinic acid (CHEBI:15940)
5-hydroxy-6-methylpyridine-3-carboxylic acid (CHEBI:15821) has functional parent nicotinic acid (CHEBI:15940)
5-pyridoxic acid (CHEBI:16409) has functional parent nicotinic acid (CHEBI:15940)
6-aminonicotinic acid (CHEBI:68583) has functional parent nicotinic acid (CHEBI:15940)
6-hydroxynicotinic acid (CHEBI:16168) has functional parent nicotinic acid (CHEBI:15940)
Euphorbia diterpenoid 2 (CHEBI:65884) has functional parent nicotinic acid (CHEBI:15940)
myo-inositol hexanicotinate (CHEBI:31699) has functional parent nicotinic acid (CHEBI:15940)
N-methylnicotinic acid (CHEBI:50521) has functional parent nicotinic acid (CHEBI:15940)
D-ribosylnicotinic acid (CHEBI:27748) has functional parent nicotinic acid (CHEBI:15940)
benzyl nicotinate (CHEBI:31268) has functional parent nicotinic acid (CHEBI:15940)
boscalid (CHEBI:81822) has functional parent nicotinic acid (CHEBI:15940)
clonixin (CHEBI:76200) has functional parent nicotinic acid (CHEBI:15940)
cyclitol nicotinate (CHEBI:50135) has functional parent nicotinic acid (CHEBI:15940)
flunixin (CHEBI:76138) has functional parent nicotinic acid (CHEBI:15940)
hyponine D (CHEBI:132388) has functional parent nicotinic acid (CHEBI:15940)
hyponine E (CHEBI:132389) has functional parent nicotinic acid (CHEBI:15940)
inositol hexanicotinate (CHEBI:33064) has functional parent nicotinic acid (CHEBI:15940)
nicotinamide (CHEBI:17154) has functional parent nicotinic acid (CHEBI:15940)
regelidine (CHEBI:132396) has functional parent nicotinic acid (CHEBI:15940)
vitamin B complex (CHEBI:75782) has part nicotinic acid (CHEBI:15940)
nicotinic-d4 acid (CHEBI:145116) is a nicotinic acid (CHEBI:15940)
nicotinate (CHEBI:32544) is conjugate base of nicotinic acid (CHEBI:15940)
IUPAC Names
nicotinic acid
pyridine-3-carboxylic acid
INNs Sources
acide nicotinique WHO MedNet
ácido nicotínico WHO MedNet
acidum nicotinicum WHO MedNet
nicotinic acid WHO MedNet
Synonyms Sources
3-carboxylpyridine ChemIDplus
3-carboxypyridine NIST Chemistry WebBook
3-pyridinecarboxylic acid KEGG COMPOUND
3-Pyridylcarboxylic acid HMDB
anti-pellagra vitamin NIST Chemistry WebBook
β-pyridinecarboxylic acid ChEBI
m-pyridinecarboxylic acid NIST Chemistry WebBook
Niacin
Note: (2015-01-13) Note that the term 'niacin' has also been used as a synonym for nicotinamide, as well as other molecules that exhibit the biological activity of nicotinic acid.
KEGG COMPOUND
Nicotinic acid KEGG COMPOUND
NICOTINIC ACID PDBeChem
Nicotinsaure ChemIDplus
Nikotinsäure ChEBI
P.P. factor
Note: (2015-01-13) Note that the term 'P.P. factor' has also been used as a synonym for nicotinamide.
NIST Chemistry WebBook
pellagra preventive factor NIST Chemistry WebBook
PP factor
Note: (2015-01-13) Note that the term 'PP factor' has also been used as a synonym for nicotinamide.
NIST Chemistry WebBook
pyridine-β-carboxylic acid NIST Chemistry WebBook
pyridine-carboxylique-3 ChemIDplus
vitamin B3
Note: (2015-01-13) Note that the term 'vitamin B3' has been used as a synonym for nicotinamide, as well as other molecules that exhibit the biological activity of nicotinic acid.
ChEBI
Brand Names Sources
Niacor KEGG DRUG
Niaspan KEGG DRUG
Manual Xrefs Databases
2835 DrugCentral
913 ChemSpider
C00000208 KNApSAcK
C00253 KEGG COMPOUND
D00049 KEGG DRUG
DB00627 DrugBank
FDB001014 FooDB
HMDB0001488 HMDB
LSM-4676 LINCS
Niacin Wikipedia
NIACINE MetaCyc
NIO PDBeChem
View more database links
Registry Numbers Types Sources
109591 Beilstein Registry Number Beilstein
109591 Reaxys Registry Number Reaxys
3340 Gmelin Registry Number Gmelin
59-67-6 CAS Registry Number KEGG COMPOUND
59-67-6 CAS Registry Number ChemIDplus
59-67-6 CAS Registry Number NIST Chemistry WebBook
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Last Modified
22 July 2021