ChemFOnt: Showing chemical card for 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide (CFc000007229)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:27 UTC

Chemfont ID

CFc000007229

Molecule Identification

Common Name

1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide

Definition

1-(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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Reduced nicotinamide riboside	ChEBI
1-(b-D-Ribofuranosyl)-1,4-dihydronicotinamide	Generator
1-(Β-D-ribofuranosyl)-1,4-dihydronicotinamide	Generator

Chemical Formula

C₁₁H₁₆N₂O₅

Average Molecular Weight

256.2551

Monoisotopic Molecular Weight

256.105921632

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide

Traditional Name

reduced nicotinamide riboside

CAS Registry Number

None

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 Key

MAKBMGXNXXXBFE-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).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dihydropyridine (CHEBI:55458 )
pyridine nucleoside (CHEBI:55458 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0011648)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	80.5 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.1	ChemAxon
logS	-0.5	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	3.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.84 m³·mol⁻¹	ChemAxon
Polarizability	24.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon