Lonomycin A
Basic information
- CAS
58785-63-0- Standard SMILES
CO[C@@H]1[C@H](C)[C@H]([C@]2(C)CC[C@H]([C@]3(C)CC[C@]4(C[C@H](OC)[C@@H](C)[C@@H]([C@@H](C)[C@H]5O[C@@](O)([C@H](C)C(=O)O)[C@H](C)[C@@H](OC)[C@H]5C)O4)O3)O2)O[C@H]1[C@H]1O[C@](C)(O)[C@H](C)[C@@H](OC)[C@@H]1C- InChIKey
BKZOUCVNTCLNFF-IGXZVFLKSA-N- Molecular formula
- C44H76O14
- Average molar mass
- 829.1 g/mol
- Monoisotopic mass
- 828.52350709
Names & identifiers
- Preferred name
- Lonomycin A
- IUPAC
- (2S)-2-[(2R,3R,4S,5R,6S)-2-hydroxy-6-[(1S)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,4R,5R)-5-[(2S,3S,4S,5R,6S)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]-4-methoxy-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-4-methoxy-3,5-dimethyloxan-2-yl]propanoic acid
- English name
- lonomycin
- Molecular formula
- C44H76O14
- Molecular weight
- 829.07
Names & synonyms
Lonomycin AEmericid58785-63-0ANTIBIOTIC DE-3936P54LV930KADTXSID501319102RefChem:154062DTXCID501748058Lonomycin(2S)-2-[(2R,3R,4S,5R,6S)-2-hydroxy-6-[(1S)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,4R,5R)-5-[(2S,3S,4S,5R,6S)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]-4-methoxy-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-4-methoxy-3,5-dimethyloxan-2-yl]propanoic acid(S)-2-((2R,3R,4S,5R,6S)-2-hydroxy-6-((S)-1-((2S,5R,7S,8R,9S)-2-((2S,2'R,3'S,4'R,5R,5'R)-5'-((2S,3S,4S,5R,6S)-6-hydroxy-4-methoxy-3,5,6-trimethyltetrahydro-2H-pyran-2-yl)-4'-methoxy-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-9-methoxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl)ethyl)-4-methoxy-3,5-dimethyltetrahydro-2H-pyran-2-yl)propanoic acidAntibiotic TM 481
Show more names
2H-Pyran-2-acetic acid, tetrahydro-2-hydroxy-4-methoxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-9-methoxy-2,8-dimethyl-2-[(2S,2'R,3'S,4'R,5R,5'R)-octahydro-4'-methoxy-2,3'-dimethyl-5'-[(2S,3S,4S,5R,6S)-tetrahydro-6-hydroxy-4-methoxy-3,5,6-trimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]e...
Properties
Computed structural properties
- XLogP
- 5.5
- Topological polar surface area
- 170 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 11
- Heavy atoms
- 58
- Formal charge
- 0
- Complexity
- 1,450
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 109 · 109-114°
- alpha
- 20 · D20 +66.6° (c = 1 in CHCl3); D23 +57.5° (c = 0.40 in CH2Cl2)
- Boiling point
- 683.74 °C · 683.74°C (rough estimate)
- Density
- 1.0642 · 1.0642 (rough estimate)
- refractive index
- 1.613 · 1.6130 (estimate)
- pka
- pKa (66% acetone) 5.9(at 25℃)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 54 LV930KA · P54LV930KA
Chemistry & industry
Applications
UsesEmericid (Lonomycin A) has anti-Gram-positive bacterial activity and can be used for the study of coccidiosis of poultry[1].
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