Molecule

Bis(Dethio)Bis(Methylthio)Gliotoxin

AlkaPlorer ID: AK023776

Synonym: None

IUPAC Name: (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-6,10-dihydro-5aH-pyrazino[1,2-a]indole-1,4-dione

Structure

SMILES: CS[C@]1(CO)C(=O)N2[C@H]3C(=CC=C[C@@H]3O)C[C@@]2(SC)C(=O)N1C

InChI: InChI=1S/C15H20N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,10-11,18-19H,7-8H2,1-3H3/t10-,11-,14+,15+/m0/s1

InChIKey: OVBAGMZLGLXSBN-UOVKNHIHSA-N

Reference

Alkaloids from the Marine Isolate of the Fungus Aspergillus fumigatus

PubChem CID: 194564

CAS: 74149-38-5

LOTUS: LTS0148976

SuperNatural Ⅲ: SN0275999-03

NPASS: NPC17581

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NPAtlas: NPA020349

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Aspergillus fumigatus	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
Saussurea macrota	Saussurea	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Lagochilus inebrians	Lagochilus	Lamiaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Elysia tuca	Elysia	Plakobranchidae	None	Gastropoda	Mollusca	Metazoa	Eukaryota
Penicillium sp.	Penicillium	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
None	Gliocladium	None	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Sterculia parviflora	Sterculia	Malvaceae	Malvales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 356.4690000000001

TPSA？: 81.08

MolLogP？: 0.0272999999999998

Number of H-Donors: 2

Number of H-Acceptors: 6

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	DU-145	Activity	nan	None	10.1021/np200563x
Homo sapiens	DU-145	Inhibition	22.0	%	10.1021/np200563x
Homo sapiens	Farnesyl diphosphate synthase	IC50	100000.0	nM	10.1016/j.bmc.2010.02.034
Homo sapiens	HeLa	IC50	2810.0	nM	10.1016/j.bmc.2010.02.034
Homo sapiens	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	IC50	100000.0	nM	10.1021/np200740e
Homo sapiens	Histone-lysine N-methyltransferase SETD7	Inhibition	nan	%	10.1021/np200740e
Homo sapiens	HUVEC	IC50	1120.0	nM	10.1016/j.bmc.2010.02.034
Homo sapiens	Jurkat	IC50	140000.0	nM	10.1016/j.bmc.2010.02.034
Mus musculus	Mus musculus	LD50	500.0	mg.kg-1	10.1016/j.bmc.2010.02.034
Mus musculus	P388	IC50	110.0	nM	10.1021/np200740e
Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	40200.0	nM	10.1016/j.bmc.2010.02.034
Trypanosoma brucei rhodesiense	Rhodesain	IC50	50000.0	nM	10.1016/j.bmc.2010.02.034
None	Macrophage	ED50	10.0	uM	10.1016/j.bmc.2010.02.034
None	Unchecked	IC50	8400.0	nM	10.1016/j.bmc.2010.02.034
None	Unchecked	IC50	50000.0	nM	10.1016/j.bmc.2010.02.034
None	Unchecked	Ratio IC50	3.5	None	10.1016/j.bmc.2010.02.034

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT012626	CS[C@@]12CC3=CC=C[C@H](O)[C@H]3N1C(=O)[C@](S)(CO)N(C)C2=O.C[SAH]>>CS[C@]1(CO)C(=O)N2[C@H]3C(=CC=C[C@@H]3O)C[C@@]2(SC)C(=O)N1C	RXN-16212