Showing Compound Nicotinamide riboside (FDB022281)

Record Information

Version

1.0

Creation date

2011-09-21 00:11:28 UTC

Update date

2020-09-17 15:38:43 UTC

Primary ID

FDB022281

Secondary Accession Numbers

FDB030199

Chemical Information

FooDB Name

Nicotinamide riboside

Description

Nicotinamide riboside, also known as N-ribosylnicotinamide or SRT-647, 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). A pyridine nucleoside consisting of nicotinamide with a beta-D-ribofuranosyl moiety at the 1-position. Nicotinamide riboside is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Within humans, nicotinamide riboside participates in a number of enzymatic reactions. In particular, nicotinamide riboside and phosphoric acid can be biosynthesized from niacinamide and ribose-1-arsenate through its interaction with the enzyme purine nucleoside phosphorylase. In addition, nicotinamide riboside can be converted into nicotinamide ribotide through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In humans, nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Outside of the human body, Nicotinamide riboside has been detected, but not quantified in, milk (cow). This could make nicotinamide riboside a potential biomarker for the consumption of these foods.

CAS Number

1341-23-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
1-(b-D-Ribofuranosyl)nicotinamide	Generator
1-(beta-D-Ribofuranosyl)nicotinamide	ChEBI
1-(Β-D-ribofuranosyl)nicotinamide	Generator
1-(β-D-ribofuranosyl)nicotinamide	Generator
1-b-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-b-D-ribosyl-3-Pyridinecarboxamide	hmdb
1-beta-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-D-ribosyl-3-Pyridinecarboxamide	hmdb
1-beta-delta-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-delta-ribosyl-3-Pyridinecarboxamide	hmdb

Showing 1 to 10 of 29 entries

Predicted Properties

Property	Value	Source
Water Solubility	5.45 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-6.1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.39	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.83 m³·mol⁻¹	ChemAxon
Polarizability	24.83 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

Chemical Formula

C11H15N2O5

IUPAC name

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

InChI Identifier

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

InChI Key

JLEBZPBDRKPWTD-TURQNECASA-O

Isomeric SMILES

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

Average Molecular Weight

255.2472

Monoisotopic Molecular Weight

255.0980966

Classification

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-glycosylnicotinamide (CHEBI:15927 )
pyridine nucleoside (CHEBI:15927 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Urine

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Nicotinamide riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-070f-9530000000-71d9e02ee640bb800185	Spectrum
Predicted GC-MS	Nicotinamide riboside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6r-9825400000-99de0fc632f408e32a12	Spectrum
Predicted GC-MS	Nicotinamide riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TMS_3_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinamide riboside, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-0190000000-51bf764225f08b566d36	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0a4i-0290000000-ffbe280293f874204044	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-05fr-0970000000-1714e669425e34d3754a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00di-0920000000-77ef12950b3152d752c8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00di-0900000000-b14d15851532222ba74a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00di-0900000000-277d95be8f0485eb3ce5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-00di-0900000000-354c1f3978635e5109bb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-00di-0900000000-ea5e376f71c6414964bc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-00di-0900000000-6b289ae1c5f53e92f774	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-00di-1900000000-6ad92fa16e2cca17f959	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-00di-1900000000-cee8757ed6b406ccf044	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-00di-2900000000-78f21d967892a0d9ab85	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, positive	splash10-00di-3900000000-cd1f66bfc8ded7bd098e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-00e9-8900000000-5a6bc8100043575c6a58	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, positive	splash10-00ai-9200000000-aedd3c5bf179b666a6ae	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-003r-9000000000-22053c801abdfaf5f562	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, positive	splash10-0fai-9000000000-b6b4b7e819e08c863a9a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-00di-0900000000-3364e345334aa7f5a742	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-004i-9000000000-3bf262f96423e85a1756	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-e25d1beb47cb1fe9e4cb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-3090000000-03687e9ef697eda1d6c8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052g-9300000000-2755bde4df843d2227f2	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-809be1146b2a2c8d96a7	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1390000000-2fc72cf0619f182e044f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k96-9300000000-4d5b96b192f3484b1b8a	2015-09-15	View Spectrum