(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(1S,3R,7R,8S,9S,10R,12R,14E,16S)-7-(acetyloxy)-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate

• ChemBase ID: 163666
• Molecular Formular: C42H67NO16
• Molecular Mass: 841.97848
• Monoisotopic Mass: 841.44598507
• SMILES: O1C(=O)C[C@H]([C@@H]([C@H]([C@H](C[C@H](C(=O)/C=C/[C@H]2[C@@H](C[C@H]1C)O2)C)CC=O)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C)O[C@@H]1O[C@@H]([C@@H]([C@@](C1)(O)C)OC(=O)CC(C)C)C)N(C)C)O)OC)OC(=O)C
• Canonical SMILES: O=CC[C@H]1C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@@H]2C[C@H](OC(=O)C[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)N(C)C)O[C@@H]1O[C@H](C)[C@@H]([C@](C1)(C)O)OC(=O)CC(C)C)OC)OC(=O)C)C
• InChI: InChI=1S/C42H67NO16/c1-21(2)16-32(47)57-40-25(6)53-34(20-42(40,8)50)58-37-24(5)54-41(36(49)35(37)43(9)10)59-38-27(14-15-44)17-22(3)28(46)12-13-29-30(56-29)18-23(4)52-33(48)19-31(39(38)51-11)55-26(7)45/h12-13,15,21-25,27,29-31,34-41,49-50H,14,16-20H2,1-11H3/b13-12+/t22-,23-,24-,25+,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
• InChIKey: FQVHOULQCKDUCY-OGHXVOSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(1S,3R,7R,8S,9S,10R,12R,14E,16S)-7-(acetyloxy)-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
• IUPAC Traditional name: (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(1S,3R,7R,8S,9S,10R,12R,14E,16S)-7-(acetyloxy)-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
• Synonyms: (12S,13S)-9-Deoxy-12,13-epoxy-12,13-dihydro-9-oxoleucomycin V 3-Acetate 4B-(3-Methylbutanoate); Carbomycin A; Carbomycin; Deltamycin A4; M 4209; Magnamycin; Magnamycin A; NSC 51001; NSC 55924; Carbomycin

Database IDs

• CAS Number: 4564-87-8
• PubChem SID: 162257801
• PubChem CID: 5287879

CALCULATED PROPERTIES

• Acid pKa: 12.662435
• H Acceptors: 14
• H Donor: 2
• LogD (pH = 5.5): 1.2535678
• LogD (pH = 7.4): 2.740269
• Log P: 2.9508445
• Molar Refractivity: 208.4457 cm^3
• Polarizability: 84.528694 Å^3
• Polar Surface Area: 215.42 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C176680

Sixteen-membered-ring macrolite antibiotic complex similar to Leucomycin and Erythromycin, produced by Stroptomyces halstedii.

REFERENCES

• Shimauchi, Y., et al.: J. Antibiot., 31, 270 (1978)
• Davis, B., et al.: J. Mol. Biol., 336, 343 (1978)
• Zhou, Y., et al.: Bioorg. Med. Chem. Lett., 17, 1206 (1978)