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Beauveriolide III

AlkaPlorer ID: AK023451

Synonym: 'FO 6979', 'Beauveriolide III'

IUPAC Name: (3R,6S,9S,13S)-9-benzyl-3-[(2S)-butan-2-yl]-13-[(2S)-hexan-2-yl]-6-methyl-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone

Structure

SMILES: CCCC[C@H](C)[C@@H]1CC(O)=N[C@@H](CC2=CC=CC=C2)C(O)=N[C@@H](C)C(O)=N[C@H]([C@@H](C)CC)C(=O)O1

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InChI: InChI=1S/C27H41N3O5/c1-6-8-12-18(4)22-16-23(31)29-21(15-20-13-10-9-11-14-20)26(33)28-19(5)25(32)30-24(17(3)7-2)27(34)35-22/h9-11,13-14,17-19,21-22,24H,6-8,12,15-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t17-,18-,19-,21-,22-,24+/m0/s1

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InChIKey: VEELKRGSLCNVAR-QVZGIDAOSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
None None Cordycipitaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 487.64100000000025

TPSA？: 124.07

MolLogP？: 5.412200000000005

Number of H-Donors: 3

Number of H-Acceptors: 5

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus aethiops Sterol O-acyltransferase 1 IC50 900.0 nM None
Chlorocebus aethiops Sterol O-acyltransferase 1 IC50 1100.0 nM 10.1016/j.bmcl.2018.03.077
Chlorocebus aethiops Sterol O-acyltransferase 1 IC50 2800.0 nM 10.1016/j.bmcl.2018.03.077
Chlorocebus aethiops Sterol O-acyltransferase 2 IC50 3100.0 nM 10.1016/j.bmcl.2018.03.077
Chlorocebus aethiops Sterol O-acyltransferase 2 IC50 20000.0 nM 10.1016/j.bmcl.2018.03.077
Chlorocebus aethiops Sterol O-acyltransferase 2 IC50 20000.0 nM None
Homo sapiens Acyl coenzyme A:cholesterol acyltransferase 1 IC50 410.0 nM 10.1016/j.bmcl.2011.10.045
Homo sapiens Acyl coenzyme A:cholesterol acyltransferase 1 IC50 900.0 nM None
Homo sapiens Acyl coenzyme A:cholesterol acyltransferase 1 IC50 5500.0 nM 10.1021/acs.jmedchem.2c01265
Homo sapiens Acyl coenzyme A:cholesterol acyltransferase 2 IC50 20000.0 nM 10.1021/acs.jmedchem.2c01265
Homo sapiens Acyl coenzyme A:cholesterol acyltransferase 2 IC50 20000.0 nM None
Mus musculus Acyl coenzyme A:cholesterol acyltransferase 1 Inhibition 91.0 % 10.1016/j.bmcl.2008.06.054
None Macrophage IC50 400.0 nM 10.1016/j.bmcl.2008.06.054
None Unchecked IC50 1190.0 nM 10.1021/acs.jmedchem.2c01265
None Unchecked -log(RatioIC50) 0.044 None 10.1016/j.bmcl.2018.03.077
None Unchecked -log(RatioIC50) 1.3 None 10.1016/j.bmcl.2018.03.077

Metabolism Information