Basic information
- CAS
1094-61-7- Standard SMILES
NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)([O-])O)[C@@H](O)[C@H]2O)c1- InChIKey
DAYLJWODMCOQEW-TURQNECASA-N- Molecular formula
- C11H15N2O8P
- Average molar mass
- 334.22 g/mol
- Monoisotopic mass
- 334.05660244
Names & identifiers
- Preferred name
- Nicotinamide Mononucleotide
- IUPAC
- [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
- English name
- β-Nicotinamide Mononucleotide
- Molecular formula
- C11H15N2O8P
- Molecular weight
- 334.22
Names & synonyms
1094-61-7nicotinamide mononucleotideNicotinamide ribotide2KG6QX4W0VPyridinium, 3-(aminocarbonyl)-1-(5-O-phosphono-beta-D-ribofuranosyl)-, inner saltDTXSID50911152[(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphateAlpha9((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl hydrogen phosphate3-carbamoyl-1-((2R,3R,4S,5R)-5-((hydrogen phosphonatooxy)methyl)-3,4-dihydroxyoxolan-2-yl)-1$l^(5)-pyridin-1-ylium3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1$l^{5}-pyridin-1-yliumELITEHEALTH
Show more names
NMNBETA-NMNβ-NMNNMN powderB-NICOTINAMIDE MONONUCLEOTIDELiposomal NMNβ-Nicotinamide Mononucleotide(NMN)
REUS NRRefChem:854107Mononucleotide, NicotinamideCHEBI:50383DTXCID001511294214-136-53-carboxy-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)oxolan-2-yl)-1lambda5-pyridin-1-yliumbeta-Nicotinamide mononucleotide
Properties
Computed structural properties
- XLogP
- -3.5
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 455
Experimental & physicochemical properties
Collision Cross Section
167.13 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
166 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
165.2 Ų [M]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]；165.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 166 °C · 166 °C(dec.)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- White to Yellow
- Merck
- 13 · 13,6697
- BRN
- 3570187 · 3570187
- Stability
- Very Hygroscopic
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- InChI
- InChI=1/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/s3
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified；Reported as not meeting GHS hazard criteria by 2 of 2 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 2 of 2 reports by companies.；There are 0 notifications provided by 0 of 2 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 8-10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2934999090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionNicotinamide mononucleotide (NMN), a product of the NAMPT reaction and a key NAD+ intermediate, ameliorates glucose intolerance by restoring NAD+ levels in HFD-induced T2D mice. NMN also enhances hepatic insulin sensitivity and restores gene expression related to oxidative stress, inflammatory response, and circadian rhythm, partly through SIRT1 activation. NMN is used for studying binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments.β-Nicotinamide mononucleotide (β-NMN) is an intermediate in the nicotinamide phosphoribosyltransferase (NAMPT)-catalyzed biosynthesis of nicotinamide adenine dinucleotide (NAD+). NAMPT mediates the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to produce β-NMN. β-NMN adenyltransferase subsequently converts β-NMN to NAD+.
Usesβ-Nicotinamide mononucleotide (NMN) is used to study binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments. NMN is a nucleotide derived from ribose and nicotinamide. Niacinamide (nicotinamide,) is a derivative of vitamin B3, also known as niacin.) As a biochemical precursor of NAD+, it may be useful in the prevention of pellagra.β-Nicotinamide mononucleotide is an intermediate in the biosynthesis of nicotinamide adenine dinucleotide (NAD+). Nicotinamide phosphoribosyltransferase (Nampt) catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to generate β-NMN, which is subsequently converted to NAD+ by β-NMN adenyltransferase.At 50-100 μM, β-NMN has been used to enhance NAD biosynthesis and glucose-stimulated insulin secretion in a Nampt+/- mouse model of metabolic disease, demonstrating a role for Nampt in β cell function.Furthermore, at 500 mg/kg/day, it has been shown to ameliorate glucose intolerance in high-fat diet-induced type 2 diabetes mice by restoring NAD+ levels.
General Descriptionβ-Nicotinamide mononucleotide (β-NMN) is an intermediate in the nicotinamide phosphoribosyltransferase (NAMPT)-catalyzed biosynthesis of nicotinamide adenine dinucleotide (NAD+). NAMPT mediates the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to produce β-NMN. β-NMN adenyltransferase subsequently converts β-NMN to NAD+.
Preparation methods
Related reactions
1 records
Compound notes
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