Nicotinamide riboside

Details

• Internal ID: d507a08c-a4bc-478f-af2e-f1be11567a4b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Glycosylamines
• IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxamide
• SMILES (Canonical): C1=CC(=C[N+](=C1)C2C(C(C(O2)CO)O)O)C(=O)N
• SMILES (Isomeric): C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
• InChI: 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
• Popularity: 295 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₅N₂O₅+
• Molecular Weight: 255.25 g/mol
• Exact Mass: 255.09809658 g/mol
• Topological Polar Surface Area (TPSA): 117.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.32
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 1341-23-7
• nicotinamide ribose
• N-ribosylnicotinamide
• nicotinamide-beta-riboside
• nicotinamide ribonucleoside
• ribosylnicotinamide
• 3-Carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium
• Niagen
• 1-(beta-D-Ribofuranosyl)nicotinamide
• Pyridinium, 3-(aminocarbonyl)-1-beta-D-ribofuranosyl-
• 0I8H2M0L7N
• CHEBI:15927
• 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxamide
• 3-carbamoyl-1-beta-D-ribofuranosylpyridinium
• TruNiagen
• SRT647
• SRT 647
• SRT-647
• N-ribosyl-nicotinamide
• beta-nicotinamide D-riboside
• UNII-0I8H2M0L7N
• SCHEMBL938611
• CHEMBL438497
• DTXSID501010039
• 1-(beta-D ribofuranosyl)nicotinamide
• 1-b-D-ribosyl-3-Pyridinecarboxamide
• AKOS040740858
• NICOTINAMIDE RIBOSIDE [WHO-DD]
• 1-beta-D-ribosyl-3-Pyridinecarboxamide
• AM84366
• DB14933
• 1-beta-delta-ribosyl-3-Pyridinecarboxamide
• HY-123033
• CS-0080934
• C03150
• 3-(aminocarbonyl)-1-beta-d-ribofuranosylpyridinium
• 3-(aminocarbonyl)-1-beta-D-ribofuranosyl-Pyridinium
• BETA-nicotinamide ribose;Beta-Nicotinamide Riboside
• Q3334152
• 3-(aminocarbonyl)-1-beta-delta-ribofuranosyl-Pyridinium
• Pyridinium, 3-(aminocarbonyl)-1-.beta.-D-ribofuranosyl-
• 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1$l^{5}-pyridin-1-ylium

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9488	94.88%
Caco-2	-	0.7961	79.61%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Nucleus	0.4609	46.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9146	91.46%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9585	95.85%
P-glycoprotein inhibitior	-	0.9274	92.74%
P-glycoprotein substrate	-	0.9179	91.79%
CYP3A4 substrate	-	0.5827	58.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	-	0.9764	97.64%
CYP2C9 inhibition	-	0.9474	94.74%
CYP2C19 inhibition	-	0.9387	93.87%
CYP2D6 inhibition	-	0.9504	95.04%
CYP1A2 inhibition	-	0.9406	94.06%
CYP2C8 inhibition	-	0.8950	89.50%
CYP inhibitory promiscuity	-	0.9673	96.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4888	48.88%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9634	96.34%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6502	65.02%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	-	0.5965	59.65%
skin sensitisation	-	0.8525	85.25%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6964	69.64%
Acute Oral Toxicity (c)	III	0.4742	47.42%
Estrogen receptor binding	-	0.7265	72.65%
Androgen receptor binding	-	0.6088	60.88%
Thyroid receptor binding	-	0.7971	79.71%
Glucocorticoid receptor binding	-	0.8278	82.78%
Aromatase binding	-	0.6168	61.68%
PPAR gamma	+	0.6464	64.64%
Honey bee toxicity	-	0.9156	91.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.9464	94.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.75%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.36%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.98%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.53%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.70%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.92%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.26%	97.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.78%	96.00%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.00%	88.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.54%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 439924
• LOTUS: LTS0260519
• wikiData: Q3334152