4-{[(3R,4S)-3,4,5-trihydroxyoxan-2-yl]amino}benzoic acid

• ChemBase ID: 179767
• Molecular Formular: C12H15NO6
• Molecular Mass: 269.2506
• Monoisotopic Mass: 269.08993721
• SMILES: [C@@H]1(C(OCC([C@@H]1O)O)Nc1ccc(C(=O)O)cc1)O
• Canonical SMILES: OC1COC([C@@H]([C@H]1O)O)Nc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C12H15NO6/c14-8-5-19-11(10(16)9(8)15)13-7-3-1-6(2-4-7)12(17)18/h1-4,8-11,13-16H,5H2,(H,17,18)/t8?,9-,10+,11?/m0/s1
• InChIKey: HLDUHCYBUVVDOT-LIZLNQBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(3R,4S)-3,4,5-trihydroxyoxan-2-yl]amino}benzoic acid
• IUPAC Traditional name: 4-{[(3R,4S)-3,4,5-trihydroxyoxan-2-yl]amino}benzoic acid
• Synonyms: 4-(Xylosylamino)benzoic acid; N -(4-Carboxyphenyl)xylosamine; Chevalizon; Benaxibine

Database IDs

• CAS Number: 27661-27-4
• PubChem SID: 164235677
• PubChem CID: 44891339

CALCULATED PROPERTIES

• Acid pKa: 4.6907325
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.5510973
• LogD (pH = 7.4): -3.3289547
• Log P: -0.68002033
• Molar Refractivity: 65.2076 cm^3
• Polarizability: 24.992062 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Cyclophosphamide synergizer

Product Information

• Application(s): Antidiabetic, antihypertensive agent; Antineoplastic agent; Immunopotentiator

REFERENCES

• Inoue, Y. et al., Nippon Nogei Kagaku Kaishi, 1951, 25, 59; CA, 48, 2001c, (synth)
• Shcherbukhin, V.D. et al., Dokl. Akad. Nauk SSSR, Ser. Khim., 1967, 174, 725; 177, 607, (ir)
• Stepanenko, B.N. et al., Dokl. Akad. Nauk SSSR, Ser. Khim., 1967, 177, 607
• U.S. Pat., 1982, Kureha, 4 315 921; CA, 96, 168753d, (synth, pharmacol)
• Toge, T. et al., Int. J. Immunopharmacol., 1984, 6, 55, (pharmacol)