bassianolide (CHEBI:145108)

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CHEBI:145108 - bassianolide

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ChEBI ID	CHEBI:145108
ChEBI Name	bassianolide
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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:	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).

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
(−)-bassianolide	ChEBI
BASS	ChEBI

UniProt Name	Source
bassianolide	UniProt

Registry Numbers	Sources
CAS:64763-82-2	ChemIDplus

Citations