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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-02-03 09:22:11 UTC
Update Date2022-09-22 18:35:07 UTC
HMDB IDHMDB0011648
Secondary Accession Numbers
  • HMDB11648
Metabolite Identification
Common Name1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide
Description1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide is the reduced form of nicotinamide riboside. Nicotinamide riboside or NR is a natural product found in milk. It can exist in both the oxidized and reduced form. Nicotinamide riboside is a newly discovered precursor to NAD ( nicotinamide adenine dinucleotide). Nicotinamide riboside kinases (Nrks) are essential for this NAD synthesis pathway. Nrks actually constitute a distinct pathway of NAD biosynthesis and it appears that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD synthesis (PMID: 18429699 ). NAD homeostasis is related to the free radical-mediated production of reactive oxygen species responsible for irreversible cellular damage in infectious disease, diabetes, inflammatory syndromes, neurodegeneration and cancer. (PMID: 18508649 ). Baseline requirements for NAD synthesis can be met either with dietary tryptophan or with less than 20 mg of daily niacin, which consists of nicotinic acid and/or nicotinamide. Reduced nicotinamide riboside is also known to be a substrate for ribosyldihydronicotinamide dehydrogenase (EC 1.10.99.2). It is also a substrate for purine-nucleoside phosphorylase (PNP) - (PMID: 9030766 ).
Structure
Thumb
Synonyms
ValueSource
Reduced nicotinamide ribosideChEBI
1-(b-D-Ribofuranosyl)-1,4-dihydronicotinamideGenerator
1-(Β-D-ribofuranosyl)-1,4-dihydronicotinamideGenerator
Chemical FormulaC11H16N2O5
Average Molecular Weight256.2551
Monoisotopic Molecular Weight256.105921632
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide
Traditional Namereduced nicotinamide riboside
CAS Registry NumberNot Available
SMILES
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H16N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1,3-4,7-9,11,14-16H,2,5H2,(H2,12,17)/t7-,8-,9-,11-/m1/s1
InChI KeyMAKBMGXNXXXBFE-TURQNECASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • N-substituted nicotinamide
  • Pentose monosaccharide
  • Dihydropyridine
  • Hydropyridine
  • Monosaccharide
  • Vinylogous amide
  • Tetrahydrofuran
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Enamine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028341
KNApSAcK IDNot Available
Chemspider ID9681931
KEGG Compound IDC15497
BioCyc IDCPD-7229
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11507134
PDB IDNot Available
ChEBI ID55458
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bogan KL, Brenner C: Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition. Annu Rev Nutr. 2008;28:115-30. doi: 10.1146/annurev.nutr.28.061807.155443. [PubMed:18429699 ]
  2. Magni G, Orsomando G, Raffelli N, Ruggieri S: Enzymology of mammalian NAD metabolism in health and disease. Front Biosci. 2008 May 1;13:6135-54. [PubMed:18508649 ]
  3. Wielgus-Kutrowska B, Kulikowska E, Wierzchowski J, Bzowska A, Shugar D: Nicotinamide riboside, an unusual, non-typical, substrate of purified purine-nucleoside phosphorylases. Eur J Biochem. 1997 Jan 15;243(1-2):408-14. [PubMed:9030766 ]

Enzymes

General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular weight:
25918.4
Reactions
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide + a quinone → 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinonedetails