sodium 1-[5-({[({[5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ5-pyridin-1-ylium

• ChemBase ID: 155081
• Molecular Formular: C21H27N7NaO17P3
• Molecular Mass: 765.386833
• Monoisotopic Mass: 765.05739661
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)COP(=O)([O-])OP(=O)([O-])OCC1C(C(C(O1)[n+]1cc(ccc1)C(=O)N)O)O)O)OP(=O)(O)O)N.[Na+]
• Canonical SMILES: OC1C(O)C(OC1[n+]1cccc(c1)C(=O)N)COP(=O)(OP(=O)(OCC1OC(C(C1O)OP(=O)(O)O)n1cnc2c1ncnc2N)[O-])[O-].[Na+]
• InChI: InChI=1S/C21H28N7O17P3.Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39);/q;+1/p-1
• InChIKey: JNUMDLCHLVUHFS-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 1-[5-({[({[5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: sodium 1-(5-{[({[5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-3-carbamoyl-1λ^5-pyridin-1-ylium
• Synonyms: Triphosphopyridine nucleotide sodium salt hydrate; β-Nicotinamide adenine dinucleotide phosphate sodium salt hydrate; 三磷酸吡啶核苷酸 钠盐 水合物

Database IDs

• CAS Number: 698999-85-8
• EC Number: 214-664-6
• MDL Number: MFCD00150480
• PubChem SID: 24889814; 162249219; 24897665; 24897427; 24897624
• PubChem CID: 53442183

CALCULATED PROPERTIES

• Acid pKa: 0.65526783
• H Acceptors: 17
• H Donor: 7
• LogD (pH = 5.5): -13.820263
• LogD (pH = 7.4): -15.519069
• Log P: -10.446874
• Molar Refractivity: 150.6264 cm^3
• Polarizability: 60.66334 Å^3
• Polar Surface Area: 370.45 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, faintly yellow
• Apperance: powder; white to yellow powder
• Melting Point: 175-178 °C (dec.)(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 1; 3
• Risk Statements: 20/21/22-36-68/20/21/22; 36
• Safety Statements: 26; 26-36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319-H371; H319
• GHS Precautionary statements: P260-P305 + P351 + P338; P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (enzymatic); ≥95% (HPLC); ≥95% (spectrophotometric assay); ≥95.0% (HPLC); ≥98% (enzymatic); ≥98% (HPLC); ≥98% (spectrophotometric assay)
• Suitability: in accordance for glucose-6-phosphate dehydrogenase test; suitable for cell culture
• Impurities: ≤8% water
• Quality Level: PREMIUM
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C21H27N7NaO17P3 · xH2O

DETAILS

Sigma Aldrich - N3139

Analysis Note
Meets or exceeds NRC specifications and is comparable to any commercial preparation available.
Biochem/physiol Actions
Electron acceptor
Other Notes
This is the common form of NADP. Do not confuse with 3′-NADP or α-NADP.
Packaging
Packaged by solid weight.

Sigma Aldrich - N3886

Biochem/physiol Actions
Electron acceptor
Other Notes
This is the common form of NADP. Do not confuse with 3′-NADP or α-NADP.
Packaging
Packaged by solid weight.
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).

Sigma Aldrich - N0505

Biochem/physiol Actions
Electron acceptor
Other Notes
This is the common form of NADP. Do not confuse with 3′-NADP or α-NADP.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0505.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0505.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Packaging
1, 5 g in poly bottle
100, 500 mg in poly bottle
Packaged by solid weight.

Sigma Aldrich - 93208

Biochem/physiol Actions
Electron acceptor
Other Notes
This is the common form of NADP. Do not confuse with 3′-NADP or α-NADP.
Packaging
Packaged by solid weight.
Application
Nicotinamide adenine dinucleotide phosphate (NADP) and NADPH form a redox pair. NADP/NADPH is a coenzyme that supports redox reactions via the transport of electrons in a vast array of applications, especially anaerobic reactions such as lipid and nucleic acid synthesis. NADP/NADPH is a coenzyme couple in various cytochrome P450 systems and oxidase/reductase reaction systems, such as the thioredoxin reductase/thioredoxin system.