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N7764

Sigma-Aldrich

Nicotinic acid mononucleotide

Synonym(s):

Nicotinate mononucleotide

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About This Item

Empirical Formula (Hill Notation):
C11H14NO9P
CAS Number:
321-02-8
Molecular Weight:
335.20
MDL number:
MFCD00070358
UNSPSC Code:
12352106
PubChem Substance ID:
24897839
NACRES:
NA.79

biological source

animal

Assay

≥98.0% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white

storage temp.

−20°C

SMILES string

OC1C(O)C(OC1COP(O)(O)=O)[N]2=CC(=CC=C2)C(O)=O

InChI

1S/C11H15NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H,15,16)(H2,17,18,19)

InChI key

IUJWGLOJJKFASX-UHFFFAOYSA-N

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General description

Nicotinic acid mononucleotide (NaMN) is formed from nicotinic acid 5-phosphoribosyl-1-pyrophosphate (PRPP) in the Preiss-Handler pathway in the presence of enzyme phosphoribosyltransferase (NaPRT).

Application

Nicotinic acid mononucleotide has been used as a substrate for NMN/NaMN adenylyltransferase (NMNAT) during nicotinamide adenine dinucleotide (NAD) biosynthesis.

Biochem/physiol Actions

Nicotinic acid mononucleotide (NaMN) may be used to study the relationship between the phosphate-responsive signaling (PHO) pathway and nicotine adenine dinucleotide (NAD(+)) metabolism in yeast. Nicotinate mononucleotide is a substrate for NMN/NaMN adenylyltransferase (NMNAT) and nicotinate mononucleotide adenylyltransferase. NaMN amidation results in the synthesis of nicotinamide mononucleotide(NMN), which is further converted to NAD cofactor.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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K Shibata et al.
Journal of chromatography. B, Biomedical sciences and applications, 749(2), 281-285 (2001-01-06)
A system has been developed for the determination of quinolinate phosphoribosyltransferase (QPRT) activity in liver and kidney homogenates using HPLC. A product, nicotinic acid mononucleotide (NaMN), is separated by reversed-phase chromatography (a Tosoh ODS 80TS was used as an analytical
Graham Noctor et al.
Journal of experimental botany, 57(8), 1603-1620 (2006-05-23)
Pyridine nucleotides are key redox carriers in the soluble phase of all living cells, and both NAD and NADP play crucial roles in pro-oxidant and antioxidant metabolism. Recent data also suggest a number of non-redox mechanisms by which these nucleotides
Regulation of NAD+ metabolism, signaling and compartmentalization in the yeast Saccharomyces cerevisiae
Kato M and Lin SJ
DNA Repair, 23, 49-58 (2014)
Nicotinamide mononucleotide synthetase is the key enzyme for an alternative route of NAD biosynthesis in Francisella tularensis
Sorci L, et al.
Proceedings of the National Academy of Sciences of the USA, 106(9), 3083-3088 (2009)
Identification of a nicotinamide/nicotinate mononucleotide adenylyltransferase in Giardia lamblia (GlNMNAT)
Forero-Baena N, et al.
Biochimie, 1, 61-69 (2015)
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