(1R,3S,8R,10R,11R,12S,13S,14S)-5-butyl-8,12,14-trihydroxy-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one

• ChemBase ID: 179354
• Molecular Formular: C17H30N2O7
• Molecular Mass: 374.4293
• Monoisotopic Mass: 374.20530131
• SMILES: [C@@H]1([C@@H]([C@H]([C@@H]2[C@@H]([C@H]1O)O[C@H]1[C@@](O2)(C(=O)CC(O1)CCCC)O)NC)O)NC
• Canonical SMILES: CCCCC1O[C@H]2O[C@@H]3[C@@H](O)[C@@H](NC)[C@@H]([C@H]([C@H]3O[C@]2(C(=O)C1)O)NC)O
• InChI: InChI=1S/C17H30N2O7/c1-4-5-6-8-7-9(20)17(23)16(24-8)25-15-13(22)10(18-2)12(21)11(19-3)14(15)26-17/h8,10-16,18-19,21-23H,4-7H2,1-3H3/t8?,10-,11+,12-,13-,14+,15+,16-,17-/m0/s1
• InChIKey: KHAUBYTYGDOYRU-KWVKPNAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,8R,10R,11R,12S,13S,14S)-5-butyl-8,12,14-trihydroxy-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^3,^8]tetradecan-7-one
• IUPAC Traditional name: (1R,3S,8R,10R,11R,12S,13S,14S)-5-butyl-8,12,14-trihydroxy-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^3,^8]tetradecan-7-one
• Synonyms: (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-2-Butyldecahydro-4a,7,9-trihydroxy-6,8-bis(methylamino)-4H-pyrano[2,3-b][1,4]benzodioxin-4-one Dihydrochloride; Trospectomycin Dihydrochloride

Database IDs

• CAS Number: 85951-37-7
• PubChem SID: 164235264
• PubChem CID: 71752873

CALCULATED PROPERTIES

• Acid pKa: 8.576961
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -4.5521693
• LogD (pH = 7.4): -2.0100822
• Log P: -0.9576938
• Molar Refractivity: 89.1622 cm^3
• Polarizability: 37.054546 Å^3
• Polar Surface Area: 129.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T892750

Spectinomycin analog useful in treatment of Chlamydia trachomatis infection in birds or mammals.

REFERENCES

• Mordenti, J., et al.: J. Pharm. Sci., 75, 1028 (1986)
• Lave, T., et al.: J. Pharm. Sci., 86, 584 (1986)
• Mahmood, I., et al.: J. Clin. Pharmacol., 40, 1439 (1986)
• Ward, K., et al.: Drug Metab. Dispos., 32, 603 (1986)
• Tang, H., et al.: J. Clin. Pharmacol