Latrunculin A
AlkaPlorer ID: AK013776
Synonym: None
IUPAC Name: (4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
Structure
SMILES: C/C1=C/C(=O)O[C@@H]2C[C@@H](CC[C@H](C)/C=C\C=C\CC1)O[C@@](O)([C@@H]1CSC(O)=N1)C2
InChI: InChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1
InChIKey: DDVBPZROPPMBLW-IZGXTMSKSA-N
Reference
PubChem CID: 445420
CAS: 76343-93-6
LOTUS: LTS0048733
SuperNatural Ⅲ: SN0063146-15
NPASS: NPC287572
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Negombata magnifica | Negombata | Latrunculiidae | Poecilosclerida | Demospongiae | Porifera | Metazoa | Eukaryota |
| Cacospongia mycofijiensis | Cacospongia | Thorectidae | Dictyoceratida | Demospongiae | Porifera | Metazoa | Eukaryota |
Properties Information
Molecule Weight: 421.5590000000002
TPSA？: 88.35000000000001
MolLogP？: 4.064000000000003
Number of H-Donors: 2
Number of H-Acceptors: 6
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Aspergillus flavus | Aspergillus flavus | Activity | nan | None | 10.1016/j.bmc.2009.09.012 |
| Candida albicans | Candida albicans | Activity | nan | None | 10.1016/j.bmc.2009.09.012 |
| Candida albicans | Candida albicans | MIC | 15.6 | ug.mL-1 | 10.1021/np50082a019 |
| Homo sapiens | 786-0 | GI50 | 226.46 | nM | None |
| Homo sapiens | A498 | GI50 | 110.92 | nM | None |
| Homo sapiens | A549 | GI50 | 563.64 | nM | None |
| Homo sapiens | A549 | IC50 | 0.06 | ug.mL-1 | 10.1021/np50096a015 |
| Homo sapiens | A549 | T/C | 146.0 | % | 10.1021/np50096a015 |
| Homo sapiens | ACHN | GI50 | 313.33 | nM | None |
| Homo sapiens | BT-549 | GI50 | 305.49 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 74.13 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 437.52 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 180.3 | nM | None |
| Homo sapiens | DU-145 | GI50 | 2773.32 | nM | None |
| Homo sapiens | EKVX | GI50 | 739.61 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 2971.67 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 772.68 | nM | None |
| Homo sapiens | HCT-116 | IC50 | 1100.0 | nM | 10.1021/jm8008585 |
| Homo sapiens | HCT-15 | GI50 | 520.0 | nM | None |
| Homo sapiens | HeLa | Activity | nan | None | 10.1021/np200673b |
| Homo sapiens | HL-60 | GI50 | 3280.95 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 178.24 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 116.14 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 114.29 | nM | None |
| Homo sapiens | HT-29 | GI50 | 416.87 | nM | None |
| Homo sapiens | HT-29 | IC50 | 0.06 | ug.mL-1 | 10.1021/np50096a015 |
| Homo sapiens | HT-29 | IC50 | 0.08 | ug.mL-1 | 10.1021/np200673b |
| Homo sapiens | Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha | IC50 | 6700.0 | nM | 10.1021/np070587w |
| Homo sapiens | Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha | IC50 | 25000.0 | nM | 10.1021/np070587w |
| Homo sapiens | IGROV-1 | GI50 | 132.74 | nM | None |
| Homo sapiens | K562 | GI50 | 3341.95 | nM | None |
| Homo sapiens | KM12 | GI50 | 10000.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 1096.48 | nM | None |
| Homo sapiens | M14 | GI50 | 564.94 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 895.36 | nM | None |
| Homo sapiens | MCF7 | GI50 | 1279.38 | nM | None |
| Homo sapiens | MCF7 | IC50 | 480.0 | nM | 10.1016/j.ejmech.2021.113491 |
| Homo sapiens | MCF7 | IC50 | 479733448.64 | nM | 10.1016/j.ejmech.2010.05.012 |
| Homo sapiens | MDA-MB-231 | Activity | 50.0 | % | 10.1016/j.ejmech.2019.03.024 |
| Homo sapiens | MDA-MB-231 | GI50 | 83.37 | nM | None |
| Homo sapiens | MDA-MB-231 | IC50 | 4190.0 | nM | 10.1016/j.ejmech.2021.113491 |
| Homo sapiens | MDA-MB-435 | GI50 | 439.54 | nM | None |
| Homo sapiens | MDA-MB-435 | IC50 | 0.04 | ug.mL-1 | 10.1021/np200673b |
| Homo sapiens | MDA-MB-435 | IC50 | 2800.0 | nM | 10.1021/jm8008585 |
| Homo sapiens | MDA-MB-435 | Ratio IC50 | 2.5 | None | 10.1021/jm8008585 |
| Homo sapiens | MDA-N | GI50 | 5069.91 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 5834.45 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 3006.08 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 271.64 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 2142.89 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 3365.12 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 799.83 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 1032.76 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 1016.25 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 484.17 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 1409.29 | nM | None |
| Homo sapiens | PC-3 | Activity | nan | None | 10.1007/s00044-013-0495-6 |
| Homo sapiens | PC-3 | GI50 | 299.23 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 10000.0 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 190.55 | nM | None |
| Homo sapiens | SF-268 | GI50 | 305.49 | nM | None |
| Homo sapiens | SF-295 | GI50 | 262.42 | nM | None |
| Homo sapiens | SF-539 | GI50 | 171.0 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 5248.07 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 1122.02 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 443.61 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 4159.11 | nM | None |
| Homo sapiens | SN12C | GI50 | 427.56 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 610.94 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 74.99 | nM | None |
| Homo sapiens | SR | GI50 | 653.13 | nM | None |
| Homo sapiens | T47D | Activity | 20.0 | % | 10.1021/np070587w |
| Homo sapiens | TK-10 | GI50 | 264.24 | nM | None |
| Homo sapiens | U-251 | GI50 | 10000.0 | nM | None |
| Homo sapiens | U-937 | IC50 | 0.07 | ug.mL-1 | 10.1021/np200673b |
| Homo sapiens | UACC-257 | GI50 | 2511.89 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 348.34 | nM | None |
| Homo sapiens | UO-31 | GI50 | 299.92 | nM | None |
| Issatchenkia orientalis | ATP binding cassette transporter Abc1p | Activity | nan | None | 10.1128/aac.01095-08 |
| Mus musculus | MC-38 | IZ | 9.0 | mm | 10.1021/jm8008585 |
| Mus musculus | Mus musculus | Activity | nan | None | 10.1021/np50096a015 |
| Mus musculus | NIH3T3 | Inhibition | 95.0 | % | 10.1016/j.ejmech.2019.03.024 |
| Mus musculus | P388 | IC50 | 4.1 | ug.mL-1 | 10.1021/np50082a019 |
| Mus musculus | P388 | IC50 | 4.1 | ug.mL-1 | 10.1021/np50096a015 |
| Mus musculus | Tyrosine-protein kinase LCK | Activity | nan | None | 10.1074/jbc.m706923200 |
| Rattus norvegicus | 3Y1 cell line | Activity | nan | None | 10.1021/acs.jnatprod.8b00101 |
| Rattus norvegicus | A10 | Activity | 0.5 | ug ml-1 | 10.1021/np0340753 |
| Rattus norvegicus | A10 | Activity | nan | None | 10.1021/jm8008585 |
| Saccharomyces cerevisiae | Saccharomyces cerevisiae | Activity | nan | None | 10.1016/j.bmc.2009.09.012 |
| Saccharomyces cerevisiae | Saccharomyces cerevisiae | Activity | nan | None | 10.1038/nchembio.100 |
| Trypanosoma brucei brucei | Trypanosoma brucei brucei | IC50 | 1.2 | ug.mL-1 | 10.1021/np200673b |
| None | NON-PROTEIN TARGET | Activity | 500.0 | nM | 10.1021/np070587w |
| None | NON-PROTEIN TARGET | Activity | nan | None | 10.1021/np070587w |
| None | NON-PROTEIN TARGET | Fold change | 3.0 | None | 10.1021/np070587w |
| None | NON-PROTEIN TARGET | IC50 | 0.06 | ug.mL-1 | 10.1021/np200673b |
| None | NON-PROTEIN TARGET | IC50 | 0.1 | ug.mL-1 | 10.1021/np50096a015 |
| None | Unchecked | Activity | nan | None | 10.1016/j.bmc.2016.04.049 |
| None | Unchecked | Activity | nan | None | 10.1021/np50096a015 |
| None | Unchecked | IC50 | 284.0 | nM | 10.1016/j.ejmech.2021.113491 |
| None | Unchecked | Inhibition | 30.0 | % | 10.1016/j.ejmech.2021.113491 |
| None | Unchecked | Inhibition | 50.0 | % | 10.1021/np50082a019 |
| None | Unchecked | Inhibition | 70.0 | % | 10.1016/j.ejmech.2021.113491 |
| None | Unchecked | Kd | 170.0 | nM | 10.1038/nchembio748 |
| None | Unchecked | Kd | 200.0 | nM | 10.1038/nchembio748 |