sodium 1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(hydrogen phosphonatooxy)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamothioyl-1λ5-pyridin-1-ylium

• ChemBase ID: 155556
• Molecular Formular: C21H27N7NaO16P3S
• Molecular Mass: 781.452433
• Monoisotopic Mass: 781.03455299
• 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(=S)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1[n+]1cccc(c1)C(=S)N)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)(O)[O-])n1cnc2c1ncnc2N)O)[O-].[Na+]
• InChI: InChI=1S/C21H28N7O16P3S.Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(43-45(32,33)34)14(30)11(42-21)6-40-47(37,38)44-46(35,36)39-5-10-13(29)15(31)20(41-10)27-3-1-2-9(4-27)18(23)48;/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,48);/q;+1/p-1/t10-,11-,13-,14-,15-,16-,20-,21-;/m1./s1
• InChIKey: RFGBSJGYGUYCBT-QYZPTAICSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-(hydrogen phosphonatooxy)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamothioyl-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: sodium 1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-(hydrogen phosphonatooxy)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamothioyl-1λ^5-pyridin-1-ylium
• Synonyms: Thionicotinamid-TPN sodium salt; Thionicotinamide-TPN; Triphosphothiopyridine nucleotide sodium salt; Thionicotinamide adenine dinucleotidephosphate sodium salt

Database IDs

• CAS Number: 19254-05-8
• MDL Number: MFCD00079598
• PubChem SID: 162249694; 24278061
• PubChem CID: 16220028

CALCULATED PROPERTIES

• Acid pKa: 0.6552737
• H Acceptors: 16
• H Donor: 7
• LogD (pH = 5.5): -12.9303665
• LogD (pH = 7.4): -14.626995
• Log P: -9.556992
• Molar Refractivity: 158.6173 cm^3
• Polarizability: 63.81105 Å^3
• Polar Surface Area: 353.38 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

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

• Purity: ≥95%
• Linear Formula: C21H27N7O16P3S · Na

DETAILS

Sigma Aldrich - T5515

Biochem/physiol Actions
Blocks nicotinate adenine dinucleotide phosphate (NAADP)-induced Ca2+ release
Linkage
Analog of NADP