bassianolide (CHEBI:145108)

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CHEBI:145108 - bassianolide

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ChEBI ID	CHEBI:145108
ChEBI Name	bassianolide
Stars
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.
Last Modified	22 August 2023
Submitter	Kristian Axelsen
Downloads	Molfile

Formula	C48H84N4O12
Net Charge	0
Average Mass	909.216
Monoisotopic Mass	908.60857
SMILES	CC(C)C[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C(C)C)C(=O)N1C
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

Species of Metabolite	Component	Source	Comments
Beauveria bassiana (ncbitaxon:176275)	-	PubMed (19285149)

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:	fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Applications:	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. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. anthelminthic drug Substance intended to kill parasitic worms (helminths).

ChEBI Ontology

Outgoing Relation(s)
	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	Source
BASS	ChEBI
(−)-bassianolide	ChEBI

UniProt Name	Source
bassianolide	UniProt

Registry Numbers	Sources
CAS:64763-82-2	ChemIDplus

Citations