sodium 10-[(2S,3S,4R)-5-(hydrogen phosphonatooxy)-2,3,4-trihydroxypentyl]-7,8-dimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

• ChemBase ID: 157770
• Molecular Formular: C17H20N4NaO9P
• Molecular Mass: 478.325631
• Monoisotopic Mass: 478.08655915
• SMILES: Cc1cc2c(cc1C)n(c1nc(=O)[nH]c(=O)c1n2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)[O-])O)O)O.[Na+]
• Canonical SMILES: O=c1[nH]c(=O)c2c(n1)n(C[C@@H]([C@@H]([C@@H](COP(=O)(O)[O-])O)O)O)c1c(n2)cc(c(c1)C)C.[Na+]
• InChI: InChI=1S/C17H21N4O9P.Na/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29;/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29);/q;+1/p-1/t11-,12+,14-;/m0./s1
• InChIKey: OHSHFZJLPYLRIP-BMZHGHOISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 10-[(2S,3S,4R)-5-(hydrogen phosphonatooxy)-2,3,4-trihydroxypentyl]-7,8-dimethyl-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
• IUPAC Traditional name: sodium 10-[(2S,3S,4R)-5-(hydrogen phosphonatooxy)-2,3,4-trihydroxypentyl]-7,8-dimethyl-3H-benzo[g]pteridine-2,4-dione
• Synonyms: Riboflavin Sodium phosphate; Riboflavini natrii phosphas; Riboflavin 5′-monophosphate sodium salt; 7,8-Dimethyl-10-ribitylisoalloxazine Phosphate Sodium; 5'-(Dihydrogen Phosphate)riboflavin Sodium; Riboflavine 5-Phosphate Sodium; Riboflavin Mononucleotide Sodium; Riboflavine Monophosphate Sodium; Riboflavine Phosphate Sodium; Vitamin B2 Phosphate Sodium; Riboflavin Phosphate Sodium Salt; 核黄素磷酸钠; 核黄素5′-单磷酸 钠盐

Database IDs

• CAS Number: 130-40-5
• EC Number: 204-988-6
• MDL Number: MFCD00065362
• Beilstein Number: 4106529
• PubChem SID: 24887210; 162251907
• PubChem CID: 23666409

CALCULATED PROPERTIES

• Acid pKa: 1.492115
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.4604461
• LogD (pH = 7.4): -4.892447
• Log P: -1.0401063
• Molar Refractivity: 106.0196 cm^3
• Polarizability: 39.881233 Å^3
• Polar Surface Area: 204.41 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Orange Solid
• Melting Point: >210°C (dec.)

Safety Information

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

Product Information

• Grade: Ph Eur
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C17H20N4NaO9P

DETAILS

Toronto Research Chemicals - R415000

One of the bioactive forms of Riboflavin. Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

REFERENCES

• Unna, K., et al.: J. Pharmacol. Exp. Ther., 76, 75 (1942)
• Rivlin, et al.: N. Engl. J. Med., 283, 463 (1942)
• Al-Shammary, F.J., et al.: Anal. Profiles Drug Subs., 19, 429 (1942)