Molecule

Beauvericin

AlkaPlorer ID: AK019838

Synonym: None

IUPAC Name: (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

Structure

SMILES: CC(C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC2=CC=CC=C2)N(C)C1=O

InChI: InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1

InChIKey: GYSCAQFHASJXRS-FFCOJMSVSA-N

Reference

Biosynthesis of beauvericin and enniatins in vitro by wheat Fusarium species and natural grain contamination in an area of central Italy

PubChem CID: 3007984

CAS: 26048-05-5

LOTUS: LTS0216693

NPASS: NPC89923

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Beauveria bassiana	Beauveria	Cordycipitaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Fusarium sporotrichioides	Fusarium	Nectriaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Fusarium poae	Fusarium	Nectriaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Guignardia sp.	Guignardia	Phyllostictaceae	Botryosphaeriales	Dothideomycetes	Ascomycota	Fungi	Eukaryota
Fusarium equiseti	Fusarium	Nectriaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Fusarium avenaceum	Fusarium	Nectriaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Fusarium proliferatum	Fusarium	Nectriaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 783.9630000000001

TPSA？: 139.83

MolLogP？: 4.912500000000004

Number of H-Donors: 0

Number of H-Acceptors: 9

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Candida albicans	Candida albicans	FC	16.0	None	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	FICI	0.13	None	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	FICI	0.31	None	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	MIC	1.3	ug.mL-1	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	MIC=>80	40.0	ug ml-1	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	MIC=>80	200.0	ug ml-1	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	MIC80	100.0	ug.mL-1	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	Ratio	0.013	None	10.1021/acs.jnatprod.5b00008
Candida albicans	Candida albicans	Ratio	0.25	None	10.1021/acs.jnatprod.5b00008
Homo sapiens	HepG2	IC50	1000.0	nM	10.1021/acs.jnatprod.2c00555
Homo sapiens	Huh-7	IC50	4300.0	nM	10.1021/acs.jnatprod.2c00555
Homo sapiens	SU.86.86	Activity	nan	None	10.1016/j.bmc.2019.115279
None	Unchecked	IC50	5600.0	nM	10.1021/acs.jmedchem.2c01265
None	Unchecked	IC50	8700.0	nM	10.1021/acs.jnatprod.2c00555

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT006177	CC(C)[C@@H](O)C(=O)O.CC(C)[C@@H](O)C(=O)O.CC(C)[C@@H](O)C(=O)O.C[SAH].C[SAH].C[SAH]>>CC(C)[C@H]1OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](Cc2ccccc2)N(C)C1=O	62276