FComEx: Nicotinamide ribotide (PC000457)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:48 UTC

Update date

2017-01-19 02:36:24 UTC

FoodComEx ID

PC000457

FoodDB Record

FDB021912

Chemical Information

Name

Nicotinamide ribotide

Description

Nicotinamide ribotide (NMN) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. Mammals predominantly use nicotinamide rather than nicotinic acid as a precursor for NAD biosynthesis. Instead of the deamidation to nicotinic acid, nicotinamide is directly converted to NMN by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme nicotinamide mononucleotide adenylyltransferase (NMNAT, EC 2.7.7.1), a member of the nucleotidyltransferase alpha/beta-phosphodiesterase superfamily, catalyzes the reaction NMN + ATP = Nicotinamide adenine dinucleotide (NAD) + PPi, representing the final step in the biosynthesis of NAD, a molecule playing a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis, and circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171, 17983582) [HMDB]

CAS Number

1094-61-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
3-(Aminocarbonyl)-1-(5-O-onato-b-D-ribofuranosyl)pyridinium	Generator
3-(Aminocarbonyl)-1-(5-O-onato-beta-D-ribofuranosyl)pyridinium	ChEBI
3-(Aminocarbonyl)-1-(5-O-onato-β-D-ribofuranosyl)pyridinium	Generator
3-(Aminocarbonyl)-1-(5-O-ONO-b-D-ribofuranosyl)-pyridinium hydroxide inner salt	HMDB
3-(Aminocarbonyl)-1-(5-O-ONO-b-D-ribofuranosyl)-pyridinium inner salt	HMDB
3-(Aminocarbonyl)-1-(5-O-ONO-b-D-ribofuranosyl)pyridinium, inner salt	Generator
3-(Aminocarbonyl)-1-(5-O-ONO-beta-D-ribofuranosyl)pyridinium, inner salt	ChEBI
3-(Aminocarbonyl)-1-(5-O-ONO-beta-delta-ribofuranosyl)-pyridinium hydroxide inner salt	HMDB
3-(Aminocarbonyl)-1-(5-O-ONO-beta-delta-ribofuranosyl)-pyridinium inner salt	HMDB
3-(Aminocarbonyl)-1-(5-O-ONO-β-D-ribofuranosyl)pyridinium, inner salt	Generator
3-(aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium hydroxide inner salt	hmdb
3-(aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-Pyridinium inner salt	hmdb
3-(aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium hydroxide inner salt	hmdb
3-(aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-Pyridinium inner salt	hmdb
3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-ate inner salt	HMDB
3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt	hmdb
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ate inner salt	HMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt	hmdb
b-D-NMN	hmdb
b-Nicotinamide D-ribonucleotide	Generator
b-Nicotinamide mononucleotide	Generator
b-Nicotinamide ribonucleotide	Generator
b-NMN	hmdb
beta-delta-NMN	hmdb
beta-Nicotinamide D-ribonucleotide	ChEBI
beta-Nicotinamide mononucleotide	ChEBI
beta-Nicotinamide ribonucleotide	ChEBI
beta-NMN	hmdb
Nicotinamide D-ribonucleotide	hmdb
Nicotinamide mononucleotide	hmdb
Nicotinamide nucleotide	ChEBI
Nicotinamide ribonucleoside 5'-ate	HMDB
Nicotinamide ribonucleoside 5'-phosphate	hmdb
Nicotinamide ribonucleotide	hmdb
NMN	hmdb
β-nicotinamide D-ribonucleotide	Generator
β-nicotinamide mononucleotide	Generator
β-nicotinamide ribonucleotide	Generator

Chemical Formula

C11H15N2O8P

IUPAC name

3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium

InChI Identifier

InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1

InChI Key

DAYLJWODMCOQEW-TURQNECASA-N

Isomeric SMILES

NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O

Average Molecular Weight

334.2192

Monoisotopic Molecular Weight

334.056601978

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyridine nucleotides

Sub Class

Nicotinamide nucleotides

Direct Parent

Nicotinamide nucleotides

Alternative Parents