Milk Composition Database: Showing metabocard for Nicotinamide riboside (BMDB0000855)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:34 UTC

Update Date

2020-05-21 16:28:55 UTC

MCDB ID

BMDB0000855

Secondary Accession Numbers

BMDB00855

Metabolite Identification

Common 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). Nicotinamide riboside is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Nicotinamide riboside participates in a number of enzymatic reactions, within cattle. In particular, Nicotinamide riboside and phosphoric acid can be biosynthesized from niacinamide and ribose-1-arsenate; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, Nicotinamide riboside can be converted into nicotinamide ribotide; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In cattle, nicotinamide riboside is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(beta-D-Ribofuranosyl)nicotinamide	ChEBI
beta-Nicotinamide D-riboside	ChEBI
Nicotinamide ribonucleoside	ChEBI
Nicotinamide ribose	ChEBI
Nicotinamide-beta-riboside	ChEBI
N-Ribosylnicotinamide	Kegg
1-(b-D-Ribofuranosyl)nicotinamide	Generator
1-(Β-D-ribofuranosyl)nicotinamide	Generator
b-Nicotinamide D-riboside	Generator
Β-nicotinamide D-riboside	Generator
Nicotinamide-b-riboside	Generator
Nicotinamide-β-riboside	Generator
1-b-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-delta-Ribosyl-3-pyridinecarboxamide	HMDB
3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-pyridinium	HMDB
3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-pyridinium	HMDB
Ribosylnicotinamide	HMDB
SRT-647	HMDB
SRT 647	HMDB

Chemical Formula

C₁₁H₁₅N₂O₅

Average Molecular Weight

255.2472

Monoisotopic Molecular Weight

255.0980966

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1341-23-7

SMILES

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

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

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
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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-070f-9530000000-71d9e02ee640bb800185	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a6r-9825400000-99de0fc632f408e32a12	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0a4i-0190000000-51bf764225f08b566d36	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0a4i-0290000000-ffbe280293f874204044	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-05fr-0970000000-1714e669425e34d3754a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00di-0920000000-77ef12950b3152d752c8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00di-0900000000-b14d15851532222ba74a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00di-0900000000-277d95be8f0485eb3ce5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-00di-0900000000-354c1f3978635e5109bb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-00di-0900000000-ea5e376f71c6414964bc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-00di-0900000000-6b289ae1c5f53e92f774	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-00di-1900000000-6ad92fa16e2cca17f959	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-00di-1900000000-cee8757ed6b406ccf044	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-00di-2900000000-78f21d967892a0d9ab85	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, positive	splash10-00di-3900000000-cd1f66bfc8ded7bd098e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-00e9-8900000000-5a6bc8100043575c6a58	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, positive	splash10-00ai-9200000000-aedd3c5bf179b666a6ae	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-003r-9000000000-22053c801abdfaf5f562	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, positive	splash10-0fai-9000000000-b6b4b7e819e08c863a9a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-00di-0900000000-3364e345334aa7f5a742	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-004i-9000000000-3bf262f96423e85a1756	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-e25d1beb47cb1fe9e4cb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-3090000000-03687e9ef697eda1d6c8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052g-9300000000-2755bde4df843d2227f2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-809be1146b2a2c8d96a7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1390000000-2fc72cf0619f182e044f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k96-9300000000-4d5b96b192f3484b1b8a	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details

External Links

HMDB ID

HMDB0000855

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022281

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Nicotinamide riboside

METLIN ID

5818

PubChem Compound

439924

PDB ID

Not Available

ChEBI ID

15927

References

Synthesis Reference

Franchetti, Palmarisa; Pasqualini, Michela; Petrelli, Riccardo; Ricciutelli, Massimo; Vita, Patrizia; Cappellacci, Loredana. Stereoselective synthesis of nicotinamide b-riboside and nucleoside analogs. Bioorganic & Medicinal Chemistry Letters (2004), 14(18), 4655-4658 Yang, T, Chan NY, Sauve AA. Syntheses of nicotinamide riboside and deriviatives.. J. Med Chem. 50:6458-61 (2007)..

Material Safety Data Sheet (MSDS)

Not Available

General References

Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

Showing metabocard for Nicotinamide riboside (BMDB0000855)

Structure for BMDB0000855 (Nicotinamide riboside)