disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy(2,3,4,5-13C4)oxolan-2-yl](13C)methyl {[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl phosphonato]oxy}phosphonate

• ChemBase ID: 168992
• Molecular Formular: C27H31N9Na2O15P2
• Molecular Mass: 834.47667619
• Monoisotopic Mass: 834.13779735
• SMILES: n1cnc2c(c1N)ncn2[13C@H]1[13C@@H]([13C@@H]([13C@H](O1)[13CH2]OP(=O)(OP(=O)(OC[C@@H]([C@@H]([C@@H](Cn1c2c(cc(c(c2)C)C)nc2c1nc(=O)[nH]c2=O)O)O)O)[O-])[O-])O)O.[Na+].[Na+]
• Canonical SMILES: O=c1[nH]c(=O)c2c(n1)n(C[C@H]([C@H]([C@H](COP(=O)(OP(=O)(O[13CH2][13C@H]1O[13C@H]([13C@@H]([13C@@H]1O)O)n1cnc3c1ncnc3N)[O-])[O-])O)O)O)c1c(n2)cc(c(c1)C)C.[Na+].[Na+]
• InChI: InChI=1S/C27H33N9O15P2.2Na/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);;/q;2*+1/p-2/t14?,15?,16-,19?,20-,21-,26-;;/m1../s1/i7+1,16+1,20+1,21+1,26+1
• InChIKey: XLRHXNIVIZZOON-SKUXAOQOSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy(2,3,4,5-^1^3C₄)oxolan-2-yl](^1^3C)methyl {[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl phosphonato]oxy}phosphonate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy(2,3,4,5-^1^3C₄)oxolan-2-yl](^1^3C)methyl [(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-3H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl phosphonato]oxyphosphonate
• Synonyms: NSC 112207; Riboflavin-adenine Dinucleotide-13C5 Dinucleotide Disodium; Flavine Adenine Dinucleotide-13C5 Disodium Salt; Flavine Adenosine Diphosphate-13C5 Disodium; Flavitan-13C5 Disodium; Riboflavin 5'-(Trihydrogen Diphosphate) P'5'-Ester with Adenosine-13C5 Disodium; Adenine-flavine Dinucleotide-13C5 Disodium; Adenine-riboflavin-13C5 Dinucleotide Disodium; Adenine-riboflavine-13C5 Dinucleotide Disodium; FAD-13C5 Disodium; Fademin-13C5 Disodium; Flavinat-13C5 Disodium

Database IDs

• PubChem SID: 162263124
• PubChem CID: 71316763

CALCULATED PROPERTIES

• Acid pKa: 1.8570329
• H Acceptors: 19
• H Donor: 7
• LogD (pH = 5.5): -7.1268997
• LogD (pH = 7.4): -7.9570637
• Log P: -5.5192356
• Molar Refractivity: 175.1874 cm^3
• Polarizability: 67.83721 Å^3
• Polar Surface Area: 362.08 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F371502

Labelled Flavine Adenine Dinucleotide. The prosthetic group of certain flavoproteins including D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. Riboflavin kinase tumor necrosis factor receptor

REFERENCES

• DeLuca, K., et al.: J. Biol. Chem., 223, 569 (1956)
• Yagi, K., et al.: Biochemistry, 19, 1553 (1956)
• Li, G., et al.: J. Phys. Chem., 112, 4573 (1956)