Cannabis Compound Database: Showing Compound Card for Nicotinamide riboside (CDB004867)

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Record Information

Version

1.0

Created at

2020-04-17 18:44:58 UTC

Updated at

2020-11-18 16:38:53 UTC

CannabisDB ID

CDB004867

Secondary Accession Numbers

Not Available

Cannabis Compound 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). 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. Nicotinamide riboside is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

255.25

Monoisotopic Molecular Weight

255.0981

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

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Nicotinate and Nicotinamide Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
5'-nucleotidase	NT5E	6q14-q21	P21589	details
Cytosolic 5'-nucleotidase 1B	NT5C1B	2p24.2	Q96P26	details
Cytosolic 5'-nucleotidase 1A	NT5C1A	1p34.3-p33	Q9BXI3	details
5'(3')-deoxyribonucleotidase, cytosolic type	NT5C		Q8TCD5	details
5'(3')-deoxyribonucleotidase, mitochondrial	NT5M		Q9NPB1	details
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	6p25.2	P16083	details
Cytosolic 5'-nucleotidase 3	NT5C3	7p14.3	Q9H0P0	details
Cytosolic purine 5'-nucleotidase	NT5C2	10q24.32	P49902	details
Purine nucleoside phosphorylase	PNP	14q13.1	P00491	details
Nicotinamide riboside kinase 1	NMRK1	9q21.13	Q9NWW6	details
Nicotinamide riboside kinase 2	NMRK2	19p13.3	Q9NPI5	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
5'-nucleotidase	NT5E	6q14-q21	P21589	details
Cytosolic 5'-nucleotidase 1B	NT5C1B	2p24.2	Q96P26	details
Cytosolic 5'-nucleotidase 1A	NT5C1A	1p34.3-p33	Q9BXI3	details
5'(3')-deoxyribonucleotidase, cytosolic type	NT5C		Q8TCD5	details
5'(3')-deoxyribonucleotidase, mitochondrial	NT5M		Q9NPB1	details
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	6p25.2	P16083	details
Cytosolic 5'-nucleotidase 3	NT5C3	7p14.3	Q9H0P0	details
Cytosolic purine 5'-nucleotidase	NT5C2	10q24.32	P49902	details
Nicotinamide riboside kinase 1	NMRK1	9q21.13	Q9NWW6	details
Nicotinamide riboside kinase 2	NMRK2	19p13.3	Q9NPI5	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

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

General References

Not Available

Only showing the first 10 proteins. There are 21 proteins in total.

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Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Enzyme Details

4. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Enzyme Details

5. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Enzyme Details

6. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

Enzyme Details

7. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Enzyme Details

8. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

Enzyme Details

9. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

Enzyme Details

10. Nicotinamide riboside kinase 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN). The enzyme also phosphorylates the antitumor drugs tiazofurin and 3-deazaguanosine.
Gene Name:: NMRK1
Uniprot ID:: Q9NWW6
Molecular weight:: 20152.76

Only showing the first 10 proteins. There are 21 proteins in total.

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Showing Compound Card for Nicotinamide riboside (CDB004867)

Structure for CDB004867 (Nicotinamide riboside)

Enzymes