CHEBI:52646 - leptomycin B

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ChEBI Name leptomycin B
ChEBI ID CHEBI:52646
Definition A leptomycin having a (2E,10E,12E,16Z,18E)-double bond configuration as well as an ethyl substituent at position 17.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C33H48O6
Net Charge 0
Average Mass 540.73060
Monoisotopic Mass 540.345
InChI InChI=1S/C33H48O6/c1-9-28(14-15-29-24(5)13-16-31(36)39-29)19-22(3)12-10-11-21(2)17-25(6)32(37)27(8)33(38)26(7)18-23(4)20-30(34)35/h10-11,13-17,19-20,22,24-27,29,33,38H,9,12,18H2,1-8H3,(H,34,35)/b11-10+,15-14+,21-17+,23-20+,28-19-/t22-,24+,25-,26+,27-,29+,33-/m1/s1
InChIKey YACHGFWEQXFSBS-XYERBDPFSA-N
SMILES CC\C(\C=C\[C@@H]1OC(=O)C=C[C@@H]1C)=C\[C@H](C)C\C=C\C(\C)=C\[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C\C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing leptomycin B (CHEBI:52646) has functional parent tetracosanoic acid (CHEBI:28866)
leptomycin B (CHEBI:52646) has role antifungal agent (CHEBI:35718)
leptomycin B (CHEBI:52646) has role bacterial metabolite (CHEBI:76969)
leptomycin B (CHEBI:52646) is a hydroxy polyunsaturated fatty acid (CHEBI:140345)
leptomycin B (CHEBI:52646) is a leptomycin (CHEBI:52651)
IUPAC Name
(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
Synonyms Sources
antibiotic ATS 1287B ChEBI
Antibiotic CI 940 ChemIDplus
Antibiotic CL 1957A ChemIDplus
Antibiotic PD 114720 ChEBI
ATS 1287B ChEBI
LMB ChEBI
Registry Numbers Types Sources
7958583 Beilstein Registry Number Beilstein
8299374 Reaxys Registry Number Reaxys
8299374 Beilstein Registry Number Beilstein
87081-35-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10421839 PubMed citation Europe PMC
10430904 PubMed citation Europe PMC
11134317 PubMed citation Europe PMC
12468543 PubMed citation Europe PMC
16964287 PubMed citation Europe PMC
6874586 PubMed citation Europe PMC
9683540 PubMed citation Europe PMC
Last Modified
05 March 2018
General Comment
2011-03-16 The dominant and most-studied member of the leptomycin class isolated from selected Streptomyces strains, it is a nanomolar-active, specific nuclear export inhibitor. Its target is CRM1/exportin1, a protein in the nuclear export sequence (NES). Leptomycin B also shows antifungal, antibacterial and potent antitumour activities.