erythromycin
C₃₇H₆₇NO₁₃·733.900 g/mol·CID 12560
IUPAC: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,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
Also known as: 114-07-8, Erythromycin A, Abomacetin, Emgel, Erymax (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
733.900g/mol
Exact Mass
733.461241Da
Monoisotopic Mass
733.461241Da
XLogP
2.7
Polar Surface Area
194.0Ų
Complexity
1180
Formal Charge
0
H-Bond Donors
5
H-Bond Acceptors
14
Rotatable Bonds
7
Heavy Atoms
51
Stereo Centers
18
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✗ 733.9 g/mol
MW ≤ 500
✓ 2.7
LogP ≤ 5
✓ 5
H-bond donors ≤ 5
✗ 14
H-bond acceptors ≤ 10
2 violations — poor oral bioavailability predicted
GHS Hazard Classification
Danger
Hazards
H317May cause an allergic skin reactionH319Causes serious eye irritationH334May cause allergy or asthma symptoms or breathing difficulties if inhaledH400Very toxic to aquatic lifeH410Very toxic to aquatic life with long lasting effects
Source: PubChem GHS Classification. Always consult the SDS for handling.
Chemical IdentifiersSMILES · InChI
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
Isomers8 compounds with formula C₃₇H₆₇NO₁₃
(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-(methylamino)oxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 11072636 · 733.9 g/mol
6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 3255 · 733.9 g/mol
14-ethyl-12,13-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-6-[3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 13923912 · 733.9 g/mol
(4S,6R,7S,11S,13S)-6-[(2S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 16757675 · 733.9 g/mol
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 44451949 · 733.9 g/mol
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2R,3S,4R,6S)-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
CID 8233 · 733.9 g/mol
(6R,7S,9R,11R,12R,13S)-6-[(3R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 10897911 · 733.9 g/mol
(3R,4R,5S,6S,7R,9S,11R,12S,13S,14S)-6-[(2S,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CID 6604221 · 733.9 g/mol