CHEBI:52650 - leptomycin A

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ChEBI Name leptomycin A
ChEBI ID CHEBI:52650
Definition A leptomycin having all-trans double bonds and a seventh methyl substituent at position 17.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H46O6
Net Charge 0
Average Mass 526.70400
Monoisotopic Mass 526.32944
InChI InChI=1S/C32H46O6/c1-20(16-22(3)12-14-28-24(5)13-15-30(35)38-28)10-9-11-21(2)17-25(6)31(36)27(8)32(37)26(7)18-23(4)19-29(33)34/h9,11-17,19-20,24-28,32,37H,10,18H2,1-8H3,(H,33,34)/b11-9+,14-12+,21-17+,22-16+,23-19+/t20-,24+,25-,26+,27-,28+,32-/m1/s1
InChIKey QECBVZBMGUAZDL-JSADDXMJSA-N
SMILES C[C@H](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)\C=C(/C)\C=C\[C@@H]1OC(=O)C=C[C@@H]1C
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 A (CHEBI:52650) has functional parent tetracosanoic acid (CHEBI:28866)
leptomycin A (CHEBI:52650) has role antifungal agent (CHEBI:35718)
leptomycin A (CHEBI:52650) has role bacterial metabolite (CHEBI:76969)
leptomycin A (CHEBI:52650) is a hydroxy polyunsaturated fatty acid (CHEBI:140345)
leptomycin A (CHEBI:52650) is a leptomycin (CHEBI:52651)
IUPAC Name
(2E,5S,6R,7S,9R,10E,12E,15R,16E,18E)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-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
(2E,10E,12E,16Z,18E)-(R)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxo-nonadeca-2,10,12,16,18-pentaenoic acid ChEBI
Antibiotic ATS 1287A ChEBI
Antibiotic PD 118607 ChEBI
Jildamycin ChemIDplus
Registry Numbers Types Sources
13029203 Reaxys Registry Number Reaxys
87081-36-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
4077736 PubMed citation Europe PMC
4077736 PubMed citation Europe PMC
6874585 PubMed citation Europe PMC
6874586 PubMed citation Europe PMC
Last Modified
05 March 2018
General Comment
2011-03-16 A methyl (cf. ethyl) analogue of leptomycin B and a minor component of the leptomycin complex produced by selected Streptomyces species, it is likely to inhibit nuclear transport, possibly showing differences in exporter selectivity from its B analogue. It shows antimicrobial activity against Schizosaccaromyces pombe and Mucor rouxianus.