ChemFOnt: Showing chemical card for Nicotinic acid ribonucleoside (CFc000002941)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:56 UTC

Chemfont ID

CFc000002941

Molecule Identification

Common Name

Nicotinic acid ribonucleoside

Definition

Nicotinic acid ribonucleoside (CAS: 17720-18-2) 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). Nicotinic acid ribonucleoside is involved in the nicotinate and nicotinamide metabolism pathways. Nicotinic acid ribonucleoside can be reversibly converted into nicotinate and nicotinate D-ribonucleoside by purine-nucleoside phosphorylase (EC 2.4.2.1) and 5'-nucleotidase (EC 3.1.3.5), respectively.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Nicotinic acid riboside	ChEBI
beta-D-Ribosylnicotinate	Kegg
Nicotinate riboside	Generator
b-D-Ribosylnicotinate	Generator
b-D-Ribosylnicotinic acid	Generator
beta-D-Ribosylnicotinic acid	Generator
Β-D-ribosylnicotinate	Generator
Β-D-ribosylnicotinic acid	Generator
Nicotinic acid D-ribonucleoside	Generator
D-Ribosylnicotinate	HMDB
Nicotinic acid ribose	HMDB
Ribosylnicotinate	HMDB
Nicotinate ribonucleoside	HMDB
Nicotinate ribose	HMDB
Nicotinic acid ribonucleoside	HMDB
3-Carboxy-1-beta-D-ribofuranosylpyridinium	HMDB
3-Carboxy-1-β-D-ribofuranosylpyridinium	HMDB
Nicotinic riboside	HMDB

Chemical Formula

C₁₁H₁₄NO₆

Average Molecular Weight

256.232

Monoisotopic Molecular Weight

256.082112185

IUPAC Name

3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium

Traditional Name

3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium

CAS Registry Number

4013-06-3

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)[N+]1=CC=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/p+1/t7-,8-,9-,10-/m1/s1

InChI Key

PUEDDPCUCPRQNY-ZYUZMQFOSA-O

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
Pentose monosaccharide
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Monosaccharide
Pyridine
Pyridinium
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Alcohol
Primary alcohol
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridine nucleoside (CHEBI:27748 )

Functional Ontology

Not Available

Feces (PMID: 24628373)

Source

Endogenous

Endogenous (HMDB: HMDB0006809)

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

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotinate and Nicotinamide Metabolism (HMDB: HMDB0006809)
Nicotinate and Nicotinamide Metabolism (PathBank: SMP0121074)
NAD Metabolism (PathBank: SMP0002338)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.34 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-5.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.01 m³·mol⁻¹	ChemAxon
Polarizability	24.21 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