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

• ChemBase ID: 130977
• Molecular Formular: C21H28N7NaO17P3
• Molecular Mass: 766.394773
• Monoisotopic Mass: 766.06522164
• 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)OP(=O)(O)O)O)N.[Na]
• Canonical SMILES: OC1C(O)C(OC1[n+]1cccc(c1)C(=O)N)COP(=O)(OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)[O-].[Na]
• InChI: InChI=1S/C21H28N7O17P3.Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-15(31)16(44-46(33,34)35)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)14(30)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)
• InChIKey: BWHZOLRRNZGBAU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(5-{[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-3-carbamoyl-1λ^5-pyridin-1-ylium sodium
• IUPAC Traditional name: 1-{5-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-3-carbamoyl-1λ^5-pyridin-1-ylium sodium
• Synonyms: α-NADP; α-TPN; α-Triphosphopyridine nucleotide; α-Nicotinamide adenine dinucleotide phosphate sodium salt

Database IDs

• CAS Number: 108392-03-6
• MDL Number: MFCD00084722
• PubChem SID: 24897544; 162225255
• PubChem CID: 71308367

CALCULATED PROPERTIES

• Acid pKa: 0.82009673
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -13.761248
• LogD (pH = 7.4): -15.371912
• Log P: -10.353
• Molar Refractivity: 151.7481 cm^3
• Polarizability: 60.781956 Å^3
• Polar Surface Area: 367.62 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 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: ≥90%
• Impurities: ≤1% β-isomer

DETAILS

Sigma Aldrich - N2010

Caution
This is not the common NADP required in the usual enzyme systems.
Other Notes
α analog of β-NADP