Leptomycin B
(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid
Molecular Identity
Leptomycin B
(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid
PubChem CID: 6917907
Leptomycin B is a leptomycin having a (2E,10E,12E,16Z,18E)-double bond configuration as well as an ethyl substituent at position 17. It has a role as an antifungal agent and a bacterial metabolite. It is a hydroxy polyunsaturated fatty acid and a leptomycin. It is functionally related to a tetracosanoic acid.
2D Structure
Properties
C33H48O6
Molecular Formula
540.70
Molecular Weight
g/mol
540.3451
Exact Mass
Da
7.9
XLogP
Above Lipinski threshold
101
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
6
H-Bond Acceptors
1020
Complexity
SMILES
Canonical SMILES
SMILES: CCC(=CC(C)CC=CC(=CC(C)C(=O)C(C)C(C(C)CC(=CC(=O)O)C)O)C)C=CC1C(C=CC(=O)O1)CIsomeric SMILES
SMILES: CC/C(=C/[C@H](C)C/C=C/C(=C/[C@@H](C)C(=O)[C@@H](C)[C@@H]([C@@H](C)C/C(=C/C(=O)O)/C)O)/C)/C=C/[C@H]1[C@H](C=CC(=O)O1)CSynonyms(20)
Leptomycin BElactocin87081-35-4Antibiotic CL 1957ACI-940Y031I2N1EOCHEBI:52646CL-1957ANSC-364372PD-114720(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid2,10,12,16,18-Nonadecapentaenoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-DTXSID9036698RefChem:152842
Data from PubChem (NCBI)
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