(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[(2H3)methyl(methyl)amino]oxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

• ChemBase ID: 164593
• Molecular Formular: C38H69NO13
• Molecular Mass: 747.95336
• Monoisotopic Mass: 747.47689127
• SMILES: [C@@]1([C@@H](CC)OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H](C(=O)[C@@H]([C@H]1O)C)C)(C)OC)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)(O)C
• Canonical SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@H](O2)C)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)OC
• InChI: InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
• InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[(^2H₃)methyl(methyl)amino]oxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• IUPAC Traditional name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[(^2H₃)methyl(methyl)amino]oxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• Synonyms: 6-O-Methylerythromycin-d3; 6-O-Methylerythromycin A-d3; A 56268-d3; Abbott 56268-d3; Antibiotic A 56268-d3; Antibiotic TE 31-d3; BIAXIN XL-d3; Biaxin-d3; CRIXAN OD-d3; Clamicin-d3; Claric-d3; Claris-d3; Claritek-d3; Clarith-d3; Clarithro-d3; Clathromycin-d3; Crixan-d3; Fascar-d3; Fromilid-d3; Kelamycin-d3; Klacid-d3; Klaribac-d3; Klaricid-d3; Klarithran MR-d3; Macladin-d3; Naxy-d3; TE 031-d3; Veclam-d3; Zeclar-d3; Clarithromycin-N-methyl-d3 (contains 2% d0)

Database IDs

• PubChem SID: 162258728
• PubChem CID: 59022393

CALCULATED PROPERTIES

• Acid pKa: 12.458389
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 0.4510266
• LogD (pH = 7.4): 2.2163913
• Log P: 3.2395153
• Molar Refractivity: 190.7883 cm^3
• Polarizability: 77.6621 Å^3
• Polar Surface Area: 182.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; DMSO; Ethanol; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 127-129°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C559752

Labelled Clarithromycin (C559750). Clarithromycin is a semi-synthetic macrolide antibiotic. Clarithromycin is a derivative of Erythromycin (E650000).

REFERENCES

• Benson, C., et al.: Eur. J. Clin. Microbiol., 6, 173 (1987)
• Boyanova, L., et al.: J. Med. Microb., 61, 85 (1987)
• Lin, Z., et al.: Toxicol. Sci., 126, 114 (1987)