N-ribosylnicotinamide (CHEBI:15927)

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CHEBI:15927 - N-ribosylnicotinamide

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ChEBI Name	N-ribosylnicotinamide

ChEBI ID	CHEBI:15927

ChEBI ASCII Name	N-ribosylnicotinamide

Definition	A pyridine nucleoside consisting of nicotinamide with a β-D-ribofuranosyl moiety at the 1-position.

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

Secondary ChEBI IDs	CHEBI:7337, CHEBI:47589, CHEBI:12527, CHEBI:21786

Supplier Information	ZINC000004096036

Download	Molfile XML SDF

more structures >>

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33 34 0 0 0 0 999 V2000

-2.3877 -1.6615 0.3116 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.9222 -0.3110 0.2920 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.0253 0.6463 -0.2196 C 0 0 2 0 0 0 0 0 0 0 0 0

-4.0094 -0.0763 -0.9621 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2748 1.6331 -1.1353 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.4693 3.0641 -0.6285 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8688 3.9797 -1.5459 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8815 1.2826 -1.0893 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8110 -0.1239 -0.7717 C 0 0 1 0 0 0 0 0 0 0 0 0

0.5005 -0.4611 -0.2132 N 0 3 0 0 0 0 0 0 0 0 0 0

1.0234 -1.6413 -0.4751 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1269 0.4286 0.5339 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3665 0.1542 1.0817 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9578 -1.0739 0.8407 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2704 -1.9944 0.0415 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8548 -3.3216 -0.2484 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2495 -4.1135 -0.9447 O 0 0 0 0 0 0 0 0 0 0 0 0

4.0582 -3.6534 0.2586 N 0 0 0 0 0 0 0 0 0 0 0 0

-3.1429 -1.8090 0.8965 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5715 -0.0088 1.2790 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4889 1.1756 0.6141 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7260 0.4753 -1.3074 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6473 1.5478 -2.1563 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5346 3.2785 -0.5456 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9997 3.1692 0.3499 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9534 4.9072 -1.2883 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0195 -0.7277 -1.6552 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4819 -2.3407 -1.0943 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6634 1.3860 0.7210 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8692 0.8916 1.6914 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9248 -1.3147 1.2559 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5417 -3.0214 0.8139 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4429 -4.5236 0.0683 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 19 1 0 0 0 0

2 3 1 0 0 0 0

2 20 1 0 0 0 0

3 5 1 0 0 0 0

3 21 1 0 0 0 0

4 3 1 0 0 0 0

4 22 1 0 0 0 0

5 6 1 0 0 0 0

5 23 1 0 0 0 0

6 7 1 0 0 0 0

6 24 1 0 0 0 0

6 25 1 0 0 0 0

7 26 1 0 0 0 0

8 5 1 0 0 0 0

9 2 1 0 0 0 0

9 8 1 0 0 0 0

9 27 1 0 0 0 0

10 9 1 0 0 0 0

10 11 4 0 0 0 0

11 28 1 0 0 0 0

12 10 4 0 0 0 0

12 29 1 0 0 0 0

13 12 4 0 0 0 0

13 14 4 0 0 0 0

13 30 1 0 0 0 0

14 15 4 0 0 0 0

14 31 1 0 0 0 0

15 11 4 0 0 0 0

15 16 1 0 0 0 0

16 17 2 0 0 0 0

16 18 1 0 0 0 0

18 32 1 0 0 0 0

18 33 1 0 0 0 0

M CHG 1 10 1

M END): 19 ms

reading 33 atoms

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33 atoms created

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

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Formula

C11H15N2O5

Net Charge

Average Mass

255.24728

Monoisotopic Mass

255.09755

InChI

InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1

InChIKey

JLEBZPBDRKPWTD-TURQNECASA-O

SMILES

NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	N-ribosylnicotinamide (CHEBI:15927) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) N-ribosylnicotinamide (CHEBI:15927) has role geroprotector (CHEBI:176497) N-ribosylnicotinamide (CHEBI:15927) has role human metabolite (CHEBI:77746) N-ribosylnicotinamide (CHEBI:15927) has role mouse metabolite (CHEBI:75771) N-ribosylnicotinamide (CHEBI:15927) is a N-glycosylnicotinamide (CHEBI:25526) N-ribosylnicotinamide (CHEBI:15927) is a pyridine nucleoside (CHEBI:47896)

IUPAC Name

3-carbamoyl-1-β-D-ribofuranosylpyridinium

Synonyms	Sources
1-(beta-D-Ribofuranosyl)nicotinamide	KEGG COMPOUND
β-nicotinamide D-riboside	UniProt
N-Ribosylnicotinamide	KEGG COMPOUND
nicotinamide ribonucleoside	ChemIDplus
nicotinamide ribose	ChemIDplus
Nicotinamide riboside	PDBeChem
nicotinamide-β-riboside	ChemIDplus

Manual Xrefs	Databases
C03150	KEGG COMPOUND
NNR	PDBeChem
View more database links

Registry Numbers	Types	Sources
1341-23-7	CAS Registry Number	ChemIDplus
3912857	Beilstein Registry Number	Beilstein

Citations

Cantó C, Houtkooper RH, Pirinen E, Youn DY, Oosterveer MH, Cen Y, Fernandez-Marcos PJ, Yamamoto H, Andreux PA, Cettour-Rose P, Gademann K, Rinsch C, Schoonjans K, Sauve AA, Auwerx J (2012)
The NAD(+) precursor nicotinamide riboside enhances oxidative metabolism and protects against high-fat diet-induced obesity.
Cell metabolism 15, 838-847 [PubMed:22682224]
[show Abstract]

Bogan KL, Brenner C (2008)
Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition.
Annual review of nutrition 28, 115-130 [PubMed:18429699]
[show Abstract]

Belenky P, Racette FG, Bogan KL, McClure JM, Smith JS, Brenner C (2007)
Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+.
Cell 129, 473-484 [PubMed:17482543]
[show Abstract]

Bieganowski P, Brenner C (2004)
Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans.
Cell 117, 495-502 [PubMed:15137942]
[show Abstract]

Last Modified

26 October 2021

CHEBI:15927 - N-ribosylnicotinamide

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