3-DESMETHYLCOLCHICINE
AlkaPlorer ID: AK010592
Synonym: '', 'Acetamide, N-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzoaheptalen-7-yl)-, (S)-', 'COLCHICINE,3-DESMETHYL', 'Colchicine, O(3)-demethyl-', '3-Demethylcolchicine'
IUPAC Name: N-[(7S)-3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Structure
SMILES: COC1=C(O)C=C2CC[C@H](N=C(C)O)C3=CC(=O)C(OC)=CC=C3C2=C1OC
InChI: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-17(25)20(27-3)21(28-4)19(12)13-6-8-18(26-2)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
InChIKey: JRRUSQGIRBEMRN-HNNXBMFYSA-N
Reference
Isolation and identification of alkaloids from seeds of Colchicum latifolium s. s.
PubChem CID: 299664
CAS: 7336-33-6
LOTUS: LTS0271726
SuperNatural Ⅲ: SN0173409-01
NPASS: NPC66678
Source
Properties Information
Molecule Weight: 385.41600000000017
TPSA？: 97.58
MolLogP？: 3.408900000000002
Number of H-Donors: 2
Number of H-Acceptors: 6
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Artemia | Artemia | LC50 | 74.6 | ug.mL-1 | 10.1021/np0496587 |
| Aspergillus niger | Aspergillus niger | MIC | 500.0 | ug.mL-1 | 10.1021/np0496587 |
| Bos taurus | Tubulin beta chain | IC50 | 2900.0 | nM | 10.1021/jm00164a015 |
| Bos taurus | Tubulin beta chain | Tubulin binding | 68.0 | % | 10.1021/jm00387a028 |
| Homo sapiens | A498 | GI50 | 140.93 | nM | None |
| Homo sapiens | A549 | GI50 | 835.6 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 95.72 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 32.51 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 84.14 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 123.59 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 32.51 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 33.27 | nM | None |
| Homo sapiens | EKVX | GI50 | 60.12 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 119.4 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 87.3 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 355.63 | nM | None |
| Homo sapiens | HL-60 | GI50 | 31.19 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 19230.92 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 219.79 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 31.19 | nM | None |
| Homo sapiens | HT-29 | GI50 | 106.66 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 162.93 | nM | None |
| Homo sapiens | K562 | GI50 | 31.19 | nM | None |
| Homo sapiens | KM12 | GI50 | 69.82 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 63.97 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 89.74 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 81.1 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 34.59 | nM | None |
| Homo sapiens | MCF7 | EC50 | 180.0 | nM | 10.1021/np0496587 |
| Homo sapiens | MCF7 | GI50 | 31.19 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 85.51 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 6966.27 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 89.54 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 137.09 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 157.4 | nM | None |
| Homo sapiens | NCI-H460 | EC50 | 510.0 | nM | 10.1021/np0496587 |
| Homo sapiens | NCI-H460 | GI50 | 92.04 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 43.85 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 32.51 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 379.31 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 311888.96 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 118.3 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 32.51 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 84.33 | nM | None |
| Homo sapiens | SF-268 | EC50 | 280.0 | nM | 10.1021/np0496587 |
| Homo sapiens | SF-268 | GI50 | 61.8 | nM | None |
| Homo sapiens | SF-295 | GI50 | 82.41 | nM | None |
| Homo sapiens | SF-539 | GI50 | 47.21 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 43.75 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 32.51 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 31.19 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 177.01 | nM | None |
| Homo sapiens | SN12C | GI50 | 239.33 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 31.19 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 191.43 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 4852.89 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 31.19 | nM | None |
| Homo sapiens | SW-620 | GI50 | 59.57 | nM | None |
| Homo sapiens | Tubulin | Tubulin binding | 68.0 | % | 10.1021/jm00135a005 |
| Homo sapiens | U-251 | GI50 | 90.36 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 4456.56 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 77.62 | nM | None |
| Homo sapiens | UO-31 | GI50 | 5834.45 | nM | None |
| Homo sapiens | XF498 | GI50 | 41.5 | nM | None |
| Micrococcus luteus | Micrococcus luteus | MIC | 500.0 | ug.mL-1 | 10.1021/np0496587 |
| Mus musculus | Mus musculus | Toxicity | 26.0 | mg kg-1 | 10.1021/jm00164a015 |
| Mus musculus | Mus musculus | Toxicity | 26.0 | uM kg-1 | 10.1021/jm00135a005 |
| Mus musculus | Mus musculus | Toxicity | 31.7 | uM kg-1 | 10.1021/jm00135a005 |
| Mus musculus | P388 | GI50 | 31.19 | nM | None |
| Mus musculus | P388 | Potency | 3.6 | uM kg-1 | 10.1021/jm00135a005 |
| Mus musculus | P388/ADR | GI50 | 9527.96 | nM | None |
| Mycolicibacterium smegmatis | Mycolicibacterium smegmatis | MIC | 500.0 | ug.mL-1 | 10.1021/np0496587 |
| Saccharomyces cerevisiae | Saccharomyces cerevisiae | MIC | 500.0 | ug.mL-1 | 10.1021/np0496587 |
| None | Unchecked | Activity | nan | None | 10.1021/acs.jnatprod.9b00880 |