Livestock Metabolome Database: Showing metabocard for Nicotinamide riboside (LMDB00263)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:57 UTC

Update Date

2016-09-23 18:45:02 UTC

Lmdb

LMDB00263

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nicotinamide riboside

Description

Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside was originally identified as a nutrient in milk. It is a useful compound for elevation of NAD+ levels in animals. Nicotinamide riboside has recently been discovered to be an NAD(+) precursor that is converted to nicotinamide mononucleotide by specific nicotinamide riboside kinases, Nrk1 and Nrk2. It has been shown that exogenous nicotinamide riboside promotes Sir2-dependent repression of recombination, improves gene silencing, and extends the lifespan of certain animal models without calorie restriction [PMID:17482543 ]. Supplementation in mammalian cells and mouse tissues increases NAD(+) levels and activates SIRT1 and SIRT3, culminating in enhanced oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities. (PMID:22682224 ). Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699 ). Nicotinamide riboside kinase has an essential role for phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID 15137942 ).

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000855

FooDB ID

FDB022281

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

41300

BioCyc ID

NICOTINAMIDE_RIBOSE

METLIN ID

5818

PDB ID

Not Available

Wikipedia Link

Nicotinamide riboside

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Belenky P, Racette FG, Bogan KL, McClure JM, Smith JS, Brenner C: Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+. Cell. 2007 May 4;129(3):473-84. [17482543 ]
Canto C, Houtkooper RH, Pirinen E, Youn DY, Oosterveer MH, Cen Y, Fernandez-Marcos PJ, Yamamoto H, Andreux PA, Cettour-Rose P, Gademann K, Rinsch C, Schoonjans K, Sauve AA, Auwerx J: The NAD(+) precursor nicotinamide riboside enhances oxidative metabolism and protects against high-fat diet-induced obesity. Cell Metab. 2012 Jun 6;15(6):838-47. doi: 10.1016/j.cmet.2012.04.022. [22682224 ]
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. [18429699 ]
Bieganowski P, Brenner C: Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans. Cell. 2004 May 14;117(4):495-502. [15137942 ]

Showing metabocard for Nicotinamide riboside (LMDB00263)

Structure for LMDB00263 (Nicotinamide riboside)