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

• ChemBase ID: 132981
• Molecular Formular: C27H33N9Na2O16P2
• Molecular Mass: 847.528682
• Monoisotopic Mass: 847.13158784
• SMILES: Cc1cc2c(cc1C)n(c1nc(=O)[nH]c(=O)c1n2)C[C@@H]([C@@H]([C@@H](COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)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)(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.O.[Na+].[Na+]
• InChI: InChI=1S/C27H33N9O15P2.2Na.H2O/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);;;1H2/q;2*+1;/p-2/t14-,15+,16+,19-,20+,21+,26+;;;/m0.../s1
• InChIKey: GXTPHHZYFMAGLX-UJXBNFGUSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium hydrate (2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: disodium hydrate (2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-3H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: FAD-Na2; FAD; Riboflavin 5′-adenosine diphosphate disodium salt; Flavin adenine dinucleotide disodium salt hydrate

Database IDs

• CAS Number: 84366-81-4
• EC Number: 282-733-8
• MDL Number: MFCD08277021
• Beilstein Number: 5326842
• PubChem SID: 162227258; 24894962; 24894909
• PubChem CID: 16219365

CALCULATED PROPERTIES

• Acid pKa: 1.8570336
• H Acceptors: 19
• H Donor: 7
• LogD (pH = 5.5): -7.1269007
• LogD (pH = 7.4): -7.9570637
• Log P: -5.519229
• 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

PROPERTIES

Physical Property

• Apperance: yellow to orange-brown powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥90% (HPLC); ≥95%; ≥95% (HPLC)
• Suitability: suitable for cell culture
• Empirical Formula (Hill Notation): C27H31N9Na2O15P2 · xH2O

DETAILS

Sigma Aldrich - F8384

Application
A redox cofactor of flavoprotins.
Flavin adenine dinucleotide (FAD) is used as a redox cofactor (electron carrier) by flavoproteins including succinate dehydrogenase (complex), α-ketoglutarate dehydrogenase, apoptosis-inducing factor 2 (AIF-M2, AMID), folate/FAD-dependent tRNA methyltransferases, and N-hydroxylating flavoprotein monooxygenases. FAD is a component of the pyruvate dehydrogenase complex.

Sigma Aldrich - F6625

Application
Flavin adenine dinucleotide (FAD) is used as a redox cofactor (electron carrier) by flavoproteins including succinate dehydrogenase (complex), α-ketoglutarate dehydrogenase, apoptosis-inducing factor 2 (AIF-M2, AMID), folate/FAD-dependent tRNA methyltransferases, and N-hydroxylating flavoprotein monooxygenases. FAD is a component of the pyruvate dehydrogenase complex.

Sigma Aldrich - 46360

Other Notes
Review1
Application
Flavin adenine dinucleotide (FAD) is used as a redox cofactor (electron carrier) by flavoproteins including succinate dehydrogenase (complex), α-ketoglutarate dehydrogenase, apoptosis-inducing factor 2 (AIF-M2, AMID), folate/FAD-dependent tRNA methyltransferases, and N-hydroxylating flavoprotein monooxygenases. FAD is a component of the pyruvate dehydrogenase complex.