CHEBI:145108 - bassianolide

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ChEBI Name bassianolide
ChEBI ID CHEBI:145108
Definition A cyclodepsipeptide consisting of a cyclic tetramer of the depsipeptide D-Hiv-N-methyl-L-leucine (where D-Hiv = D-α-hydroxyisovaleric acid). Found in the fungal species Beauveria bassiana and Verticillium lecanii, it has insecticidal properties and is used as a commercial biopesticide to control of insects of agricultural, veterinary and medical significance. For elucidation of the structure, see Suzuki et al., Tetrahedron Lett. 1977 v25, 2167-2170.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information No supplier information found for this compound.
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Formula C48H84N4O12
Net Charge 0
Average Mass 909.216
Monoisotopic Mass 908.60857
InChI InChI=1S/C48H84N4O12/c1-25(2)21-33-45(57)61-38(30(11)12)42(54)50(18)35(23-27(5)6)47(59)63-40(32(15)16)44(56)52(20)36(24-28(7)8)48(60)64-39(31(13)14)43(55)51(19)34(22-26(3)4)46(58)62-37(29(9)10)41(53)49(33)17/h25-40H,21-24H2,1-20H3/t33-,34-,35-,36-,37+,38+,39+,40+/m0/s1
InChIKey QVZZPLDJERFENQ-NKTUOASPSA-N
SMILES [C@H]1(C(N([C@H](C(=O)O[C@@H](C(N([C@H](C(=O)O[C@@H](C(N([C@H](C(=O)O[C@@H](C(N([C@H](C(=O)O1)CC(C)C)C)=O)C(C)C)CC(C)C)C)=O)C(C)C)CC(C)C)C)=O)C(C)C)CC(C)C)C)=O)C(C)C
Metabolite of Species Details
Beauveria bassiana (NCBI:txid176275) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
anthelminthic drug
Substance intended to kill parasitic worms (helminths).
(via cyclooctadepsipeptide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bassianolide (CHEBI:145108) has role antineoplastic agent (CHEBI:35610)
bassianolide (CHEBI:145108) has role fungal metabolite (CHEBI:76946)
bassianolide (CHEBI:145108) has role insecticide (CHEBI:24852)
bassianolide (CHEBI:145108) is a cyclodepsipeptide (CHEBI:35213)
bassianolide (CHEBI:145108) is a cyclooctadepsipeptide (CHEBI:78740)
IUPAC Name
(3S,6R,9S,12R,15S,18R,21S,24R)-3,9,15,21-tetraisobutyl-6,12,18,24-tetraisopropyl-4,10,16,22-tetramethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosane-2,5,8,11,14,17,20,23-octone
Synonyms Sources
(−)-bassianolide ChEBI
BASS ChEBI
bassianolide UniProt
Registry Number Type Source
64763-82-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18375793 PubMed citation Europe PMC
19285149 PubMed citation Europe PMC
23608474 PubMed citation SUBMITTER
27676608 PubMed citation Europe PMC
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29909016 PubMed citation Europe PMC
30029532 PubMed citation Europe PMC
31388353 PubMed citation Europe PMC
33058930 PubMed citation Europe PMC
36984865 PubMed citation Europe PMC
37252886 PubMed citation Europe PMC
6620728 PubMed citation Europe PMC
6953262 PubMed citation Europe PMC
IND79047232 Agricola citation Europe PMC
Last Modified
22 August 2023