Metabolite Card
Formula: C11H15N2O5 (255.0981)
SMILES: NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
Synonyms [en]
nicotinamide-beta-riboside; 1-(beta-D-Ribofuranosyl)nicotinamide; nicotinamide ribose; nicotinamide riboside; nicotinamide ribonucleoside; N-ribosylnicotinamide
Last reviewed on 2024-06-28.
Cite this Page
Nicotinamide-beta-riboside. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000015183). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside was originally identified as a nutrient in milk. It is a useful compound for the elevation of NAD+ levels in humans. Nicotinamide riboside has recently been discovered to be an NAD(+) precursor that is converted into nicotinamide mononucleotide by specific nicotinamide riboside kinases, Nrk1 and Nrk2. It has been shown that exogenous nicotinamide riboside promotes Sir2-dependent repression of recombination, improves gene silencing, and extends the lifespan of certain animal models without calorie restriction (PMID: 17482543). Supplementation in mammalian cells and mouse tissues increases NAD(+) levels and activates SIRT1 and SIRT3, culminating in enhanced oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities (PMID: 22682224). Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699). Nicotinamide riboside kinase has an essential role in the phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID: 15137942).
DBLinks
- CAS Registry Number: 1341-23-7
- PubChem CID: 439924
- ChEBI: 15927
- HMDB: HMDB0000855
- LipidMaps:
- KEGG: C03150
- BioCyc: NICOTINAMIDE_RIBOSE
- NCBI MeSH: nicotinamide-beta-riboside
- Wikipedia: Nicotinamide riboside
Other DBLinks
- CAS Registry Number: 1341-23-7
- PubChem: 439924
- ChEBI: ChEBI:15927
- HMDB: HMDB0000855
- KEGG: C03150
- BioCyc: NICOTINAMIDE_RIBOSE
- NCBI MeSH: nicotinamide-beta-riboside
- Wikipedia: Nicotinamide riboside
- Wikipedia: Nicotinamide_riboside
- DrugBank: DB14933
- RefMet: RM0156507
- Coconut NaturalProduct: CNP0605187.1
Class / Ontology
- WishartLab ClassyFire: [Carbohydrates and carbohydrate conjugates] Carbohydrates and carbohydrate conjugates
- RefMet: [Nicotinic acid alkaloids] Nicotinic acid alkaloids
- ChEBI: [CHEBI:15927] N-ribosylnicotinamide
- Coconut NaturalProduct: [Pyridine alkaloids] Pyridine alkaloids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R01273 | 3.2.2.3 | N-ribosylnicotinamide ribohydrolase |
| KEGG:R02294 | 2.4.2.1 | N-ribosylnicotinamide:orthophosphate ribosyltransferase |
| KEGG:R02323 | 3.1.3.5 | nicotinamide ribonucleotide phosphohydrolase |
| KEGG:R02324 | 2.7.1.22 | ATP:N-ribosylnicotinamide 5'-phosphotransferase |
| KEGG:R07361 | 1.10.5.1 | 1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide:quinone oxidoreductase |
| BioCyc:RXN-5841 | 3.1.3.5 | NICOTINAMIDE_NUCLEOTIDE + WATER --> NICOTINAMIDE_RIBOSE + Pi |
| BioCyc:RIBOSYLNICOTINAMIDE-KINASE-RXN | 2.7.1.22 | NICOTINAMIDE_RIBOSE + ATP --> PROTON + NICOTINAMIDE_NUCLEOTIDE + ADP |
| BioCyc:TRANS-RXN0-481 | NICOTINAMIDE_RIBOSE --> NICOTINAMIDE_RIBOSE | |
| BioCyc:RXN0-7092 | 2.4.2.- | NICOTINAMIDE_RIBOSE + Pi --> NIACINAMIDE + RIBOSE-1P + PROTON |
| Rhea:RHEA:12365 | 1.10.5.1 | 1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ => β-nicotinamide D-riboside + a quinol |
| Rhea:RHEA:12366 | 1.10.5.1 | β-nicotinamide D-riboside + a quinol => 1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ |
| Rhea:RHEA:12367 | 1.10.5.1 | 1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ <=> β-nicotinamide D-riboside + a quinol |
| Rhea:RHEA:14018 | 2.7.1.22 | β-nicotinamide D-riboside + ATP => β-nicotinamide D-ribonucleotide + ADP + H+ |
| Rhea:RHEA:14019 | 2.7.1.22 | β-nicotinamide D-ribonucleotide + ADP + H+ => β-nicotinamide D-riboside + ATP |
| Rhea:RHEA:14020 | 2.7.1.22 | β-nicotinamide D-riboside + ATP <=> β-nicotinamide D-ribonucleotide + ADP + H+ |
| Rhea:RHEA:30744 | β-nicotinamide D-riboside + H2O => D-ribose + nicotinamide + H+ | |
| Rhea:RHEA:30745 | D-ribose + nicotinamide + H+ => β-nicotinamide D-riboside + H2O | |
| Rhea:RHEA:30746 | β-nicotinamide D-riboside + H2O <=> D-ribose + nicotinamide + H+ | |
| Rhea:RHEA:30816 | β-nicotinamide D-ribonucleotide + H2O => β-nicotinamide D-riboside + phosphate | |
| Rhea:RHEA:30817 | β-nicotinamide D-riboside + phosphate => β-nicotinamide D-ribonucleotide + H2O |
Taxonomy Source
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:META_PWY-3502 | superpathway of NAD biosynthesis in eukaryotes |
| BioCyc:ARA_PWY-5381 | pyridine nucleotide cycling (plants) |
| BioCyc:MTBH37RV_NAD-BIOSYNTHESIS-II | NAD salvage pathway III (to nicotinamide riboside) |
| BioCyc:BSUB_PWY3O-4106 | NAD salvage pathway IV (from nicotinamide riboside) |
| BioCyc:FLY_NAD-BIOSYNTHESIS-II | NAD salvage pathway II |
| BioCyc:SYNEL_PWY3O-4106 | NAD salvage pathway III |
| BioCyc:META_PWY-5381 | pyridine nucleotide cycling (plants) |
| BioCyc:AURANTIMONAS_NAD-BIOSYNTHESIS-II | NAD salvage pathway III (to nicotinamide riboside) |
| BioCyc:CALBI_PWY3O-4106 | nicotinamide riboside salvage pathway |
| BioCyc:BSUB_NAD-BIOSYNTHESIS-II | NAD salvage pathway III (to nicotinamide riboside) |
| BioCyc:FLY_PWY3O-4106 | NAD salvage pathway III |
| BioCyc:META_PWY3O-4106 | NAD salvage pathway IV (from nicotinamide riboside) |
| BioCyc:META_NAD-BIOSYNTHESIS-II | NAD salvage pathway III (to nicotinamide riboside) |
| BioCyc:ECO_PWY3O-4106 | NAD salvage pathway IV (from nicotinamide riboside) |
| BioCyc:YEAST_PWY3O-96 | nicotinamide riboside salvage pathway II |
| BioCyc:YEAST_PWY3O-4106 | nicotinamide riboside salvage pathway I |
| WikiPathways:WP2487 | NAD salvage pathway II |
| WikiPathways:WP2488 | NAD salvage pathway III |
| PathBank:SMP0000850 | NAD Salvage |
| PlantCyc:ARA_PWY-5381 | pyridine nucleotide cycling (plants) |