Cytochalasin E
AlkaPlorer ID: AK009804
Synonym: None
IUPAC Name: (1S,5E,7R,9S,11E,13S,14S,16R,17S,18S,19S)-19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-5,11-diene-3,8,21-trione
Structure
SMILES: C[C@H]1C/C=C/[C@H]2[C@@H]3O[C@]3(C)[C@@H](C)[C@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@]32OC(=O)O/C=C/[C@@](C)(O)C1=O
InChI: InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28+/m0/s1
InChIKey: LAJXCUNOQSHRJO-ZYGJITOWSA-N
Reference
Structure of rosellichalasin, a new metabolite produced by Rosellinia necatrix.
PubChem CID: 5458385
CAS: 36011-19-5
LOTUS: LTS0214592
SuperNatural Ⅲ: SN0200247-09
NPASS: NPC4108
{NPAtlas: NPA017108
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Mycotypha sp. | Mycotypha | Mycotyphaceae | Mucorales | Mucoromycetes | Mucoromycota | Fungi | Eukaryota |
| Rhinocladiella sp. | Rhinocladiella | Herpotrichiellaceae | Chaetothyriales | Eurotiomycetes | Ascomycota | Fungi | Eukaryota |
Properties Information
Molecule Weight: 495.5720000000002
TPSA？: 117.95000000000002
MolLogP？: 3.929200000000003
Number of H-Donors: 2
Number of H-Acceptors: 7
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 5.91 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | 9.25 | % | 10.1016/j.bmc.2012.09.040 |
| Homo sapiens | 786-0 | GI50 | 114.02 | nM | None |
| Homo sapiens | A498 | GI50 | 18.11 | nM | None |
| Homo sapiens | A549 | GI50 | 25.29 | nM | None |
| Homo sapiens | A549 | IC50 | 6.2 | nM | 10.1021/np050201m |
| Homo sapiens | ACHN | GI50 | 10.0 | nM | None |
| Homo sapiens | BT-549 | GI50 | 39.17 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 13.21 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 20.99 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 16.07 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 10.33 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 54.83 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 90.99 | nM | None |
| Homo sapiens | DU-145 | GI50 | 10.0 | nM | None |
| Homo sapiens | EKVX | GI50 | 74.99 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 138.36 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 50.0 | nM | None |
| Homo sapiens | HCT-116 | IC100 | 0.244 | ug ml-1 | 10.1021/np0002942 |
| Homo sapiens | HCT-15 | GI50 | 83.37 | nM | None |
| Homo sapiens | HL-60 | GI50 | 83.75 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 17.1 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 20.56 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 23.93 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 17.06 | nM | None |
| Homo sapiens | HT-29 | GI50 | 19.45 | nM | None |
| Homo sapiens | HUVEC | IC50 | 11.4 | nM | 10.1021/np200108h |
| Homo sapiens | IGROV-1 | GI50 | 53.58 | nM | None |
| Homo sapiens | K562 | GI50 | 1721.87 | nM | None |
| Homo sapiens | KM12 | GI50 | 17498.47 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 24.77 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 12.82 | nM | None |
| Homo sapiens | M14 | GI50 | 43.65 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 75.86 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 25.12 | nM | None |
| Homo sapiens | MCF7 | GI50 | 29.17 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 10.0 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 18879.91 | nM | None |
| Homo sapiens | MDA-N | GI50 | 23.07 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 8590.14 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 5688.53 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 33.27 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 197.24 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 559.76 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 16.07 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 43.15 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 97.5 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 26.18 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 11297.96 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 23550.49 | nM | None |
| Homo sapiens | PC-3 | GI50 | 14.09 | nM | None |
| Homo sapiens | P-glycoprotein 1 | Activity | 190.0 | % | None |
| Homo sapiens | RPMI-8226 | GI50 | 555.9 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 11.07 | nM | None |
| Homo sapiens | SF-268 | GI50 | 63.83 | nM | None |
| Homo sapiens | SF-295 | GI50 | 41.88 | nM | None |
| Homo sapiens | SF-539 | GI50 | 16.9 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 392.64 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 200.45 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 21.13 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 29.17 | nM | None |
| Homo sapiens | SN12C | GI50 | 3162.28 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 10.0 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 60.39 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 10.19 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 18.92 | nM | None |
| Homo sapiens | SR | GI50 | 65.01 | nM | None |
| Homo sapiens | SW-620 | GI50 | 21777.1 | nM | None |
| Homo sapiens | SW-620 | IC100 | 0.977 | ug ml-1 | 10.1021/np0002942 |
| Homo sapiens | TK-10 | GI50 | 10.0 | nM | None |
| Homo sapiens | U-251 | GI50 | 18.79 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 263.03 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 100.0 | nM | None |
| Homo sapiens | UO-31 | GI50 | 19.91 | nM | None |
| Homo sapiens | XF498 | GI50 | 18.28 | nM | None |
| Mus musculus | P388 | GI50 | 16.6 | nM | None |
| Mus musculus | P388 | IC50 | 93.0 | nM | 10.1021/np050201m |
| Mus musculus | P388/ADR | GI50 | 314.05 | nM | None |
| None | NON-PROTEIN TARGET | IC100 | 0.0153 | ug ml-1 | 10.1021/np0002942 |
| None | NON-PROTEIN TARGET | IC50 | 11.0 | nM | 10.1021/np200108h |
| None | Unchecked | Activity | 72.0 | % | 10.1016/j.ejmech.2020.112502 |