4-ethyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.01,8]tetradecan-6-yl 2-[(5-amino-4H-1,2,4-triazol-3-yl)sulfanyl]acetate

• ChemBase ID: 160940
• Molecular Formular: C24H38N4O4S
• Molecular Mass: 478.64792
• Monoisotopic Mass: 478.26137672
• SMILES: C(C(=O)OC1CC(C(C(C23C(C1(C(CC3)C)C)C(=O)CC2)C)O)(CC)C)Sc1[nH]c(nn1)N
• Canonical SMILES: CCC1(C)CC(OC(=O)CSc2nnc([nH]2)N)C2(C)C(C)CCC3(C(C1O)C)C2C(=O)CC3
• InChI: InChI=1S/C24H38N4O4S/c1-6-22(4)11-16(32-17(30)12-33-21-26-20(25)27-28-21)23(5)13(2)7-9-24(14(3)19(22)31)10-8-15(29)18(23)24/h13-14,16,18-19,31H,6-12H2,1-5H3,(H3,25,26,27,28)
• InChIKey: FMHQJXGMLMSMLC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-ethyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-[(5-amino-4H-1,2,4-triazol-3-yl)sulfanyl]acetate
• IUPAC Traditional name: 4-ethyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-[(5-amino-4H-1,2,4-triazol-3-yl)sulfanyl]acetate
• Synonyms: 14-O-(5-(2-Amino1,3,4-triazolyl)thioacetyl)dihydromutilin; Antibiotic TDM 85-530; SA 85530b; Azamulin

Database IDs

• CAS Number: 76530-44-4
• PubChem SID: 162255075
• PubChem CID: 46780507

CALCULATED PROPERTIES

• Acid pKa: 9.322073
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.1707406
• LogD (pH = 7.4): 3.1668313
• Log P: 3.1713765
• Molar Refractivity: 129.7197 cm^3
• Polarizability: 50.300186 Å^3
• Polar Surface Area: 131.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >128°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A801530

It is a highly selective human CYP3A4 inhibitor. A mutilin derivative.

REFERENCES

• Ballard, S., et al.: Biochem. Pharmacol., 37, 4643 (1988)
• Baldwin, S., et al.: Xenobiotica, 25, 261 (1988)
• Chiba, M., et al.: Biochem. Pharmacol., 62, 773 (1988)
• Bjornsson, T., et al.: Drug Metab. Dispos., 31, 815 (1988)