Molecule

Thailanstatin A

AlkaPlorer ID: AK071279

Synonym: None

IUPAC Name: 2-[(3R,4R,5R,7S)-5-[(1E,3E)-5-[(2S,3S,5R,6R)-5-[[(Z,4S)-4-acetyloxypent-2-enoyl]amino]-3,6-dimethyloxan-2-yl]-3-methylpenta-1,3-dienyl]-4-hydroxy-1,6-dioxaspiro[2.5]octan-7-yl]acetic acid

Structure

SMILES: CC(=O)O[C@@H](C)/C=C\C(O)=N[C@@H]1C[C@H](C)[C@H](C/C=C(C)/C=C/[C@H]2O[C@H](CC(=O)O)C[C@@]3(CO3)[C@@H]2O)O[C@@H]1C

InChI: InChI=1S/C28H41NO9/c1-16(7-10-24-27(34)28(15-35-28)14-21(38-24)13-26(32)33)6-9-23-17(2)12-22(19(4)37-23)29-25(31)11-8-18(3)36-20(5)30/h6-8,10-11,17-19,21-24,27,34H,9,12-15H2,1-5H3,(H,29,31)(H,32,33)/b10-7+,11-8-,16-6+/t17-,18-,19+,21+,22+,23-,24+,27+,28+/m0/s1

InChIKey: GJKQDOMCDFJANR-FUDLAKRJSA-N

Reference

Genomics-Guided Discovery of Thailanstatins A, B, and C As Pre-mRNA Splicing Inhibitors and Antiproliferative Agents from <i>Burkholderia thailandensis</i> MSMB43

PubChem CID: 71665768

LOTUS: LTS0062498

NPASS: NPC1385

{

NPAtlas: NPA008640

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Burkholderia sp.	Burkholderia	Burkholderiaceae	Burkholderiales	Betaproteobacteria	Pseudomonadota	None	Bacteria
Burkholderia sp. FERM BP-3421	Burkholderia	Burkholderiaceae	Burkholderiales	Betaproteobacteria	Pseudomonadota	None	Bacteria

Properties Information

Molecule Weight: 535.6340000000004

TPSA？: 147.41

MolLogP？: 3.2875000000000014

Number of H-Donors: 3

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	BT-474	IC50	145.0	nM	10.1021/np500342m
Homo sapiens	DU-145	GI50	1.11	nM	10.1021/np300913h
Homo sapiens	HEK293	IC50	650.0	nM	10.1021/np300913h
Homo sapiens	HEK-293T	IC50	296.2	nM	10.1021/acs.jnatprod.1c00100
Homo sapiens	MDA-MB-231	GI50	2.58	nM	10.1021/np300913h
Homo sapiens	MDA-MB-468	IC50	142.0	nM	10.1021/np500342m
Homo sapiens	MES-SA	IC50	418.6	nM	10.1021/acs.jnatprod.1c00100
Homo sapiens	MES-SA/Dx5	IC50	400.0	nM	10.1021/acs.jnatprod.1c00100
Homo sapiens	NCI-H1975	IC50	320.0	nM	10.1021/np500342m
Homo sapiens	NCI-N87	IC50	59.0	nM	10.1021/np500342m
Homo sapiens	SK-OV-3	GI50	2.69	nM	10.1021/np300913h
None	NON-PROTEIN TARGET	GI50	2.26	nM	10.1021/np300913h
None	NON-PROTEIN TARGET	IC50	161.0	nM	10.1021/np500342m
None	No relevant target	LogD	-0.658	None	10.1021/np500342m
None	No relevant target	Stability	65.0	%	10.1021/np300913h
None	No relevant target	T1/2	78.0	hr	10.1021/np300913h