[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid

• ChemBase ID: 2075
• Molecular Formular: C27H33N9O15P2
• Molecular Mass: 785.549742
• Monoisotopic Mass: 785.15713466
• SMILES: Cc1cc2c(cc1C)n(C[C@@H](O)[C@@H](O)[C@H](O)CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc3c1ncnc3N)c1nc(=O)[nH]c(=O)c1n2
• Canonical SMILES: O=c1[nH]c(=O)c2c(n1)n(C[C@H]([C@H]([C@@H](CO[P@](=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc3c1ncnc3N)O)O)O)O)O)c1c(n2)cc(c(c1)C)C
• InChI: InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15-,16+,19-,20+,21-,26-/m1/s1
• InChIKey: VWWQXMAJTJZDQX-BPNHSMJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid
• IUPAC Traditional name: @flavin-adenine dinucleotide
• Synonyms: Flavin-N7 Protonated-Adenine Dinucleotide

Database IDs

• PubChem SID: 160965529; 46507048
• PubChem CID: 5702617

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7855749
• H Acceptors: 19
• H Donor: 9
• LogD (pH = 5.5): -7.100734
• LogD (pH = 7.4): -7.9569144
• Log P: -5.297286
• Molar Refractivity: 177.4308 cm^3
• Polarizability: 68.072075 Å^3
• Polar Surface Area: 356.42 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.78
• LOG S: -2.27
• Solubility (Water): 4.25e+00 g/l

DETAILS

DrugBank - DB02332

Drug information: experimental