Nicotinamide mononucleotide

Nicotinamide mononucleotide
Names
	IUPAC name 3-Carbamoyl-1-[5-O-(hydroxyphosphinato)-β-D-ribofuranosyl]pyridinium
	Other names Nicotinamide ribonucleoside 5'-phosphate; Nicotinamide D-ribonucleotide; β-Nicotinamide ribose monophosphate; Nicotinamide nucleotide;
Identifiers
CAS Number	1094-61-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3570187
ChEBI	CHEBI:16171;
ChEMBL	ChEMBL610238;
ChemSpider	13553;
ECHA InfoCard	100.012.851
EC Number	214-136-5;
KEGG	C00455;
PubChem CID	16219737;
UNII	2KG6QX4W0V ;
CompTox Dashboard (EPA)	DTXSID50911152 ;
	InChI InChI=1S/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-/m1/s1 Key: DAYLJWODMCOQEW-TURQNECASA-N;
	SMILES c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)[O-])O)O)C(=O)N;
Properties
Chemical formula	C11H15N2O8P
Molar mass	334.221 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Nicotinamide mononucleotide ("NMN" and "β-NMN") is a nucleotide derived from ribose and nicotinamide.[1] Like nicotinamide riboside, NMN is a derivative of niacin, and humans have enzymes that can use NMN to generate nicotinamide adenine dinucleotide (NADH).[1] In mice, NMN enters cells via the small intestines within 10 minutes converting to NAD+ through the Slc12a8 NMN transporter.[2]

Because NADH is a cofactor for processes inside mitochondria, for sirtuins, and for PARP, NMN has been studied in animal models as a potential neuroprotective and anti-aging agent.[3][4] Dietary supplement companies have aggressively marketed NMN products claiming those benefits.[5] Doses of up to 500 mg was shown safe in men in a recent human study at Keio University School of Medicine, Shinjuku, Tokyo Japan.[6]

Nicotinamide riboside (NR) kinase enzymes are essential for exogenously administered utilization of NR and NMN.[7][8] Some research suggests when administered exogenously, NMN must be converted to NR in order to enter a cell and be re-phosphorylated back to NMN.[7]

Molecular structure comparison of nicotinamide mononucleotide (NMN) and nicotinamide riboside (NR) [9]

The molecular structures of NMN and NR are roughly the same, except NMN has an added phosphate group. This added phosphate group makes NMN a larger molecule than NR. Some scientists believe NMN is too large to cross cellular membranes and must convert to NR before entering cells, where NAD+ biosynthesis occurs. Otherwise, NMN would need to get transported into cells by a transporter specific for NMN, such as Slc12a8.[9]

Both NR and NMN are vulnerable to extracellular degradation by CD38 enzyme,[8] which can be inhibited by compounds such as CD38-IN-78c.[10]

References

Bogan KL, Brenner C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annual Review of Nutrition. 28: 115–30. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.
"Slc12a8 is a nicotinamide mononucleotide transporter". Nature. January 2019.
Brazill JM, Li C, Zhu Y, Zhai RG (June 2017). "+ synthase… It's a chaperone… It's a neuroprotector". Current Opinion in Genetics & Development. 44: 156–162. doi:10.1016/j.gde.2017.03.014. PMC 5515290. PMID 28445802.
"Long-Term Administration of Nicotinamide Mononucleotide Mitigates Age-Associated Physiological Decline in Mice". Cell Metabolism. 13 December 2016.
Stipp D (March 11, 2015). "Beyond Resveratrol: The Anti-Aging NAD Fad". Scientific American Blog Network.
Irie, Junichiro; Inagaki, Emi; Fujita, Masataka; Nakaya, Hideaki; Mitsuishi, Masanori; Yamaguchi, Shintaro; Yamashita, Kazuya; Shigaki, Shuhei; Ono, Takashi; Yukioka, Hideo; Okano, Hideyuki (2020). "Effect of oral administration of nicotinamide mononucleotide on clinical parameters and nicotinamide metabolite levels in healthy Japanese men". Endocrine Journal. 67 (2): 153–160. doi:10.1507/endocrj.EJ19-0313. ISSN 0918-8959.
Fletcher RS, Lavery GG (October 2018). "The emergence of the nicotinamide riboside kinases in the regulation of NAD+ metabolism". Journal of Molecular Endocrinology. 61 (3): R107–R121. doi:10.1530/JME-18-0085. PMC 6145238. PMID 30307159.
Cambronne XA, Kraus WL (October 2020). "+ Synthesis and Functions in Mammalian Cells". Trends in Biochemical Sciences. 45 (10): 858–873. doi:10.1016/j.tibs.2020.05.010. PMC 7502477. PMID 32595066.
"NMN vs NR: The Differences Between These 2 NAD+ Precursors". www.nmn.com. Retrieved 2021-01-11.
Tarragó MG, Chini CC, Kanamori KS, Warner GM, Caride A, de Oliveira GC, et al. (May 2018). "+ Decline". Cell Metabolism. 27 (5): 1081–1095.e10. doi:10.1016/j.cmet.2018.03.016. PMC 5935140. PMID 29719225.

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[Bogan2008-1] Bogan KL, Brenner C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annual Review of Nutrition. 28: 115–30. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.

[2] "Slc12a8 is a nicotinamide mononucleotide transporter". Nature. January 2019.

[3] Brazill JM, Li C, Zhu Y, Zhai RG (June 2017). "+ synthase… It's a chaperone… It's a neuroprotector". Current Opinion in Genetics & Development. 44: 156–162. doi:10.1016/j.gde.2017.03.014. PMC 5515290. PMID 28445802.

[4] "Long-Term Administration of Nicotinamide Mononucleotide Mitigates Age-Associated Physiological Decline in Mice". Cell Metabolism. 13 December 2016.

[5] Stipp D (March 11, 2015). "Beyond Resveratrol: The Anti-Aging NAD Fad". Scientific American Blog Network.

[6] Irie, Junichiro; Inagaki, Emi; Fujita, Masataka; Nakaya, Hideaki; Mitsuishi, Masanori; Yamaguchi, Shintaro; Yamashita, Kazuya; Shigaki, Shuhei; Ono, Takashi; Yukioka, Hideo; Okano, Hideyuki (2020). "Effect of oral administration of nicotinamide mononucleotide on clinical parameters and nicotinamide metabolite levels in healthy Japanese men". Endocrine Journal. 67 (2): 153–160. doi:10.1507/endocrj.EJ19-0313. ISSN 0918-8959.

[pmid30307159-7] Fletcher RS, Lavery GG (October 2018). "The emergence of the nicotinamide riboside kinases in the regulation of NAD+ metabolism". Journal of Molecular Endocrinology. 61 (3): R107–R121. doi:10.1530/JME-18-0085. PMC 6145238. PMID 30307159.

[pmid32595066-8] Cambronne XA, Kraus WL (October 2020). "+ Synthesis and Functions in Mammalian Cells". Trends in Biochemical Sciences. 45 (10): 858–873. doi:10.1016/j.tibs.2020.05.010. PMC 7502477. PMID 32595066.

[:0-9] "NMN vs NR: The Differences Between These 2 NAD+ Precursors". www.nmn.com. Retrieved 2021-01-11.

[10] Tarragó MG, Chini CC, Kanamori KS, Warner GM, Caride A, de Oliveira GC, et al. (May 2018). "+ Decline". Cell Metabolism. 27 (5): 1081–1095.e10. doi:10.1016/j.cmet.2018.03.016. PMC 5935140. PMID 29719225.