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

• ChemBase ID: 132673
• Molecular Formular: C21H30N7O18P3
• Molecular Mass: 761.420283
• Monoisotopic Mass: 761.08601705
• SMILES: c1cc(c[n+](c1)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)OP(=O)(O)O)O)O)O)C(=O)N.O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)[O-].O
• InChI: InChI=1S/C21H28N7O17P3.H2O/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);1H2/t10-,11-,13-,14-,15-,16-,20-,21-;/m1./s1
• InChIKey: ZKJOXOJMGXFSPF-QYZPTAICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ^5-pyridin-1-ylium hydrate
• IUPAC Traditional name: nadp zwitterion hydrate
• Synonyms: β-NADP; Coenzyme II; NADP; TPN; Triphosphopyridinnucleotid; β-Nicotinamide adenine dinucleotide phosphate hydrate; Triphosphopyridine nucleotide; β-Nicotinamid-adenin-dinucleotid-phosphorsäure 水合物

Database IDs

• CAS Number: 53-59-8(anhydrous)
• EC Number: 200-178-1
• MDL Number: MFCD10567218
• PubChem SID: 24897747; 162226950
• PubChem CID: 16219760

CALCULATED PROPERTIES

• Acid pKa: 0.6552737
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -13.820264
• LogD (pH = 7.4): -15.519069
• Log P: -10.446861
• Molar Refractivity: 151.7481 cm^3
• Polarizability: 60.78195 Å^3
• Polar Surface Area: 367.62 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, slightly yellow

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC); ≥95% (enzymatic); ≥95% (HPLC); ≥95% (spectrophotometric assay)
• Suitability: in accordance for glucose-6-phosphate dehydrogenase test
• Impurities: ≤4% solvent (acetone); ≤9% water
• Cation Traces: sodium and potassium: ≤0.04%
• Absorbance ratio: A250/260 nm 0.83 ±0.04; A280/260 nm 0.22 ±0.03
• Empirical Formula (Hill Notation): C21H28N7O17P3 · xH2O

DETAILS

Sigma Aldrich - N5755

Biochem/physiol Actions
Electron acceptor
Other Notes
Packaged based on solid weight.
This is a common form of NADP.
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 - 93200

Biochem/physiol Actions
Electron acceptor
Other Notes
Structure and properties of malic enzyme from Bacillus stearothermophilus1
Packaged based on solid weight.
This is a common form of NADP.