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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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Shu-Ping Lu et al.
The Journal of biological chemistry, 286(16), 14271-14281 (2011-02-26)
Nicotinamide adenine dinucleotide (NAD(+)) is an essential cofactor involved in various cellular biochemical reactions. To date the signaling pathways that regulate NAD(+) metabolism remain unclear due to the dynamic nature and complexity of the NAD(+) metabolic pathways and the difficulty
Kazuo Yamada et al.
Analytical biochemistry, 352(2), 282-285 (2006-04-01)
We have developed a liquid chromatographic-tandem mass spectrometric method that is sensitive and specific and that simultaneously measures cellular NAD(+) and related compounds. Using this method, NAD(+), NAAD, NMN, NAMN, NAM, NA, ADPR, and 5'AMP were first separated over a
Determining NAD synthesis in erythrocytes.
V Micheli et al.
Methods in enzymology, 280, 211-221 (1997-01-01)
William B Black et al.
Microbial cell factories, 19(1), 150-150 (2020-07-29)
Noncanonical redox cofactors are emerging as important tools in cell-free biosynthesis to increase the economic viability, to enable exquisite control, and to expand the range of chemistries accessible. However, these noncanonical redox cofactors need to be biologically synthesized to achieve
V Sharma et al.
Structure (London, England : 1993), 6(12), 1587-1599 (1998-12-24)
. Mycobacterium tuberculosis is the single most deadly human pathogen and is responsible for nearly three million deaths every year. Recent elucidation of the mode of action of isoniazid, a frontline antimycobacterial drug, suggests that NAD metabolism is extremely critical
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