Erythromycin, Macrolide antibiotic

Key facts

Form

Solid

form

Molecular weight

733.9 Da

Molecular formula

C₃₇H₆₇NO₁₃

PubChem

16212992

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Soluble in ethanol to 100 mM

Biochemical name

(3R,7R,9R,11R,13S,14R)-6-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

Biological description

Macrolide antibiotic. Inhibits cytochrome p450 3A4 and P-glycoprotein. Binds the 50S ribosomal subunit and inhibits protein synthesis in Gram-positive and Gram-negative bacteria.

Canonical smiles

CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O

Isomeric smiles

CC[C@@H]1[C@@](C([C@H](C(=O)[C@@H](C[C@@](C(C(C([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)OC3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O

InChi

InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21?,22-,23+,24+,25-,26+,28-,29?,30?,31+,32?,34?,35-,36-,37-/m1/s1

InChiKey

ULGZDMOVFRHVEP-ZHPXUIBWSA-N

IUPAC Name

(3R,7R,9R,11R,13S,14R)-6-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione