CHEBI:74514 - 6-aminonicotinamide

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ChEBI Name 6-aminonicotinamide
Definition A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 6-aminonicotinic acid with ammonia. An inhibitor of the NADP+-dependent enzyme, 6-phosphogluconate dehydrogenase, it interferes with glycolysis, resulting in ATP depletion and synergizes with DNA-crosslinking chemotherapy drugs, such as cisplatin, in killing cancer cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C6H7N3O
Net Charge 0
Average Mass 137.13930
Monoisotopic Mass 137.05891
InChI InChI=1S/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10)
SMILES NC(=O)c1ccc(N)nc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
EC (NADP(+)-dependent decarboxylating phosphogluconate dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of NADP+-dependent decarboxylating phosphogluconate dehydrogenase (EC
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
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ChEBI Ontology
Outgoing 6-aminonicotinamide (CHEBI:74514) has functional parent 6-aminonicotinic acid (CHEBI:68583)
6-aminonicotinamide (CHEBI:74514) has role antimetabolite (CHEBI:35221)
6-aminonicotinamide (CHEBI:74514) has role EC (NADP+-dependent decarboxylating phosphogluconate dehydrogenase) inhibitor (CHEBI:74520)
6-aminonicotinamide (CHEBI:74514) has role teratogenic agent (CHEBI:50905)
6-aminonicotinamide (CHEBI:74514) is a aminopyridine (CHEBI:38207)
6-aminonicotinamide (CHEBI:74514) is a monocarboxylic acid amide (CHEBI:29347)
6-aminonicotinamide (CHEBI:74514) is a primary amino compound (CHEBI:50994)
Synonyms Sources
2-amino-5-carbamoylpyridine ChemIDplus
6-amino-3-pyridinecarboxamide NIST Chemistry WebBook
6-aminonicotinic acid amide ChEBI
6-Aminonikotinsaeureamid ChemIDplus
6-AN NIST Chemistry WebBook
6-ANA NIST Chemistry WebBook
SR 4388 NIST Chemistry WebBook
Manual Xref Database
CPD-9571 MetaCyc
View more database links
Registry Numbers Types Sources
116042 Reaxys Registry Number Reaxys
329-89-5 CAS Registry Number NIST Chemistry WebBook
329-89-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
125068 PubMed citation Europe PMC
145497 PubMed citation Europe PMC
152349 PubMed citation Europe PMC
155198 PubMed citation Europe PMC
2948367 PubMed citation Europe PMC
3156443 PubMed citation Europe PMC
6236288 PubMed citation Europe PMC
6445393 PubMed citation Europe PMC
9516960 PubMed citation Europe PMC
Last Modified
05 March 2014