Molecule

Aureobasidin A

AlkaPlorer ID: AK018414

Synonym: None

IUPAC Name: (3S,6S,9S,12R,15S,18S,21S,24S,27S)-3,6-dibenzyl-12,24-bis[(2R)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonone

Structure

SMILES: CC[C@@H](C)[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](CC2=CC=CC=C2)N=C(O)[C@H](C(C)C)N(C)C(=O)[C@@H]([C@H](C)CC)OC(=O)[C@H](C(C)(C)O)N(C)C(=O)[C@H](CC(C)C)N=C(O)[C@H](C(C)C)N(C)C1=O

InChI: InChI=1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1

InChIKey: RLMLFADXHJLPSQ-QKCBWMAHSA-N

Reference

Structure of aureobasidin A.

PubChem CID: 9919816

CAS: 127785-64-2

LOTUS: LTS0110479

{

NPAtlas: NPA024603

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Aureobasidium pullulans	Aureobasidium	Saccotheciaceae	Dothideales	Dothideomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 1101.4409999999991

TPSA？: 245.85

MolLogP？: 6.892700000000012

Number of H-Donors: 4

Number of H-Acceptors: 11

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Aspergillus flavus	Aspergillus flavus	MIC	50000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Aspergillus fumigatus	Aspergillus fumigatus	MIC	25.0	ug.mL-1	10.1021/acsmedchemlett.5b00029
Aspergillus fumigatus	Aspergillus fumigatus	MIC	50000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Aspergillus niger	Aspergillus niger	MIC	800.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Candida albicans	Candida albicans	MIC	0.05	ug.mL-1	10.1021/acsmedchemlett.5b00029
Candida albicans	Candida albicans	MIC	2000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Inositol phosphorylceramide synthase	IC50	0.2	nM	10.1128/aac.00633-08
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Inositol phosphorylceramide synthase	Inhibition	nan	%	10.1128/aac.00633-08
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Inositol phosphorylceramide synthase	Ki	0.18	nM	10.1128/aac.00633-08
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Inositol phosphorylceramide synthase	Ki	0.55	nM	10.1128/aac.00633-08
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Inositol phosphorylceramide synthase	Kinact	1.8	/us	10.1128/aac.00633-08
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Inositol phosphorylceramide synthase	Kinact	2.5	/us	10.1128/aac.00633-08
Candida parapsilosis	Candida parapsilosis	MIC	2000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Candida tropicalis	Candida tropicalis	MIC	2000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	Activity	1.46	nmol	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	Activity	2.12	nmol	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	Activity	2.51	mM	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	Activity	3.09	nmol	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	Activity	nan	None	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	FICI	0.26	None	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	MFC	8.0	ug ml-1	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	MIC	1.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	MIC	2.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	MIC	4.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	MIC	8.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Cryptococcus neoformans	Cryptococcus neoformans	MIC	16.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Homo sapiens	HEK293	Activity	75.0	%	10.1016/j.bmcl.2021.128013
Homo sapiens	HEK293	Activity	89.0	%	10.1016/j.bmcl.2021.128013
Homo sapiens	HEK293	Activity	98.0	%	10.1016/j.bmcl.2021.128013
Homo sapiens	HEK293	Inhibition	40.0	%	10.1016/j.bmcl.2021.128013
Homo sapiens	P-glycoprotein 1	IC50	2270.0	nM	10.1021/jm990955w
Issatchenkia orientalis	ATP binding cassette transporter Abc1p	Activity	nan	None	10.1128/aac.01095-08
Nakaseomyces glabratus	Nakaseomyces glabratus	MIC	2000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Neosartorya fumigata (Aspergillus fumigatus)	Aureobasidin-resistance protein	IC50	0.2	nM	10.1128/aac.00633-08
Pichia kudriavzevii	Pichia kudriavzevii	MIC	2000.0	ug.mL-1	10.1016/j.bmcl.2021.128013
Saccharomyces cerevisiae S288c	Inositol phosphorylceramide synthase catalytic subunit AUR1	IC50	0.2	nM	10.1128/aac.00633-08
Saccharomyces cerevisiae S288c	Inositol phosphorylceramide synthase catalytic subunit AUR1	Inhibition	nan	%	10.1128/aac.00633-08
Saccharomyces cerevisiae S288c	Inositol phosphorylceramide synthase catalytic subunit AUR1	Ki	0.23	nM	10.1128/aac.00633-08
Saccharomyces cerevisiae S288c	Inositol phosphorylceramide synthase catalytic subunit AUR1	Ki	1400.0	nM	10.1128/aac.00633-08
None	Erythrocyte	Activity	0.0	%	10.1016/j.bmcl.2021.128013
None	Erythrocyte	Activity	0.31	%	10.1016/j.bmcl.2021.128013
None	Erythrocyte	Activity	0.65	%	10.1016/j.bmcl.2021.128013
None	Erythrocyte	Activity	1.35	%	10.1016/j.bmcl.2021.128013
None	Erythrocyte	Activity	2.4	%	10.1016/j.bmcl.2021.128013
None	Unchecked	Activity	0.078	None	10.1016/j.bmcl.2021.128013
None	Unchecked	Activity	0.095	None	10.1016/j.bmcl.2021.128013
None	Unchecked	FC	0.2	None	10.1016/j.bmcl.2021.128013
None	Unchecked	FC	11.7	None	10.1016/j.bmcl.2021.128013
None	Unchecked	Inhibition	29.1	%	10.1016/j.bmcl.2021.128013
None	Unchecked	Inhibition	41.8	%	10.1016/j.bmcl.2021.128013
None	Unchecked	Inhibition	80.0	%	10.1016/j.bmcl.2021.128013
None	Unchecked	Ki	0.2	nM	10.1021/acsmedchemlett.5b00029