sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-phenylphenyl)amino]oxane-2-carboxylate

• ChemBase ID: 159855
• Molecular Formular: C18H18NNaO6
• Molecular Mass: 367.32839
• Monoisotopic Mass: 367.10318158
• SMILES: c1(ccccc1)c1ccc(cc1)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H](Nc2ccc(cc2)c2ccccc2)[C@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C18H19NO6.Na/c20-13-14(21)16(18(23)24)25-17(15(13)22)19-12-8-6-11(7-9-12)10-4-2-1-3-5-10;/h1-9,13-17,19-22H,(H,23,24);/q;+1/p-1/t13-,14-,15+,16-,17+;/m0./s1
• InChIKey: ZXJUCVIKNNGTAE-LXLGGMPYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-phenylphenyl)amino]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(4-phenylphenyl)amino]oxane-2-carboxylate
• Synonyms: 1-([1,1'-Biphenyl]-4-ylamino)-1-deoxy-β-D-glucopyranuronic Acid Sodium Salt; 4-Aminobiphenyl β-D-Glucuronide Sodium Salt

Database IDs

• CAS Number: 116490-30-3
• PubChem SID: 162253990
• PubChem CID: 71313161

CALCULATED PROPERTIES

• Acid pKa: 3.7492647
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.75164765
• LogD (pH = 7.4): -2.2853954
• Log P: 0.99956167
• Molar Refractivity: 99.7546 cm^3
• Polarizability: 35.69477 Å^3
• Polar Surface Area: 122.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Sparingly soluble in DMSO and Water
• Apperance: Off-White Solid
• Melting Point: >145°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A601790

A metabolite of 4-Aminobiphenyl (4-ABP).

REFERENCES

• Green, M., et al.: Cancer Res., 47, 2028 (1987)
• Dannenberg, A., et al.: J. Biol. Chem., 264, 238 (1987)
• Catania, V., et al.: Biochem. Pharmacol., 50, 509 (1987)
• Ghosheh, O., et al.: Drug Metab. Dispos., 30, 1478 (1987)