3-carboxy-1-{5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1λ5-pyridin-1-ylium

• ChemBase ID: 155312
• Molecular Formular: C11H14NO9P
• Molecular Mass: 335.203921
• Monoisotopic Mass: 335.04061766
• SMILES: c1c[n+](cc(c1)C(=O)O)C1C(C(C(O1)COP(=O)([O-])O)O)O
• Canonical SMILES: OC1C(O)C(OC1[n+]1cccc(c1)C(=O)O)COP(=O)(O)[O-]
• InChI: InChI=1S/C11H14NO9P/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,(H2-,15,16,17,18,19)
• InChIKey: JOUIQRNQJGXQDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carboxy-1-{5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: namn
• Synonyms: Nicotinic acid mononucleotide

Database IDs

• CAS Number: 321-02-8
• MDL Number: MFCD00070358
• PubChem SID: 24897839; 162249450
• PubChem CID: 4484

CALCULATED PROPERTIES

• Acid pKa: 1.200841
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -8.090809
• LogD (pH = 7.4): -9.207395
• Log P: -5.437405
• Molar Refractivity: 68.7635 cm^3
• Polarizability: 27.673597 Å^3
• Polar Surface Area: 160.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C11H14NO9P

DETAILS

Sigma Aldrich - N7764

Biochem/physiol Actions
Nicotinic acid mononucleotide (NaMN) is formed in the first step of Preiss-Handler pathway for the biosynthesis of NAD(+) by Nicotinate phosphoribosyltransferase (NaPRT, EC 2.4.2.11). Nicotinic acid mononucleotide may be used to study the relationship between the phosphate-responsive signaling (PHO) pathway and NAD(+) metabolism in yeast. Nicotinate mononucleotide is a substrate for NMN/NaMN adenylyltransferase (NMNAT).