Thailanstatin C
AlkaPlorer ID: AK071522
Synonym: None
IUPAC Name: 2-[(2S,4S,5R,6R)-4-(chloromethyl)-6-[(1E,3E)-5-[(2S,3S,5R,6R)-3,6-dimethyl-5-[[(Z,4S)-4-(2-methylpropanoyloxy)pent-2-enoyl]amino]oxan-2-yl]-3-methylpenta-1,3-dienyl]-4,5-dihydroxyoxan-2-yl]acetic acid
Structure
SMILES: CC(/C=C/[C@H]1O[C@H](CC(=O)O)C[C@@](O)(CCl)[C@@H]1O)=C\C[C@@H]1O[C@H](C)[C@H](N=C(O)/C=C\[C@H](C)OC(=O)C(C)C)C[C@@H]1C
InChI: InChI=1S/C30H46ClNO9/c1-17(2)29(37)39-20(5)9-12-26(33)32-23-13-19(4)24(40-21(23)6)10-7-18(3)8-11-25-28(36)30(38,16-31)15-22(41-25)14-27(34)35/h7-9,11-12,17,19-25,28,36,38H,10,13-16H2,1-6H3,(H,32,33)(H,34,35)/b11-8+,12-9-,18-7+/t19-,20-,21+,22+,23+,24-,25+,28+,30+/m0/s1
InChIKey: IUEAQIHFZAHMMU-WEDQMBCXSA-N
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Burkholderia thailandensis | Burkholderia | Burkholderiaceae | Burkholderiales | Betaproteobacteria | Pseudomonadota | None | Bacteria |
Properties Information
Molecule Weight: 600.149
TPSA？: 155.11
MolLogP？: 4.124500000000004
Number of H-Donors: 4
Number of H-Acceptors: 8
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | DU-145 | GI50 | 2.98 | nM | 10.1021/np300913h |
| Homo sapiens | HEK293 | IC50 | 6840.0 | nM | 10.1021/np300913h |
| Homo sapiens | HEK-293T | IC50 | 64.7 | nM | 10.1021/acs.jnatprod.1c00100 |
| Homo sapiens | MDA-MB-231 | GI50 | 8.82 | nM | 10.1021/np300913h |
| Homo sapiens | MES-SA | IC50 | 136.7 | nM | 10.1021/acs.jnatprod.1c00100 |
| Homo sapiens | MES-SA/Dx5 | IC50 | 298.5 | nM | 10.1021/acs.jnatprod.1c00100 |
| Homo sapiens | SK-OV-3 | GI50 | 5.57 | nM | 10.1021/np300913h |
| None | NON-PROTEIN TARGET | GI50 | 3.67 | nM | 10.1021/np300913h |
| None | No relevant target | T1/2 | 25.0 | hr | 10.1021/np300913h |