thalicarpine
AlkaPlorer ID: AK010609
Synonym: 'Thalicarpine', 'Taliblastine', '(+)-Thalicarpine', 'TBL'
IUPAC Name: (6aS)-9-[2-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-4,5-dimethoxyphenoxy]-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Structure
SMILES: COC1=C(OC)C=C(OC2=CC3=C(C=C2OC)C2=C(OC)C(OC)=CC4=C2[C@H](C3)N(C)CC4)C(C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C)=C1
InChI: InChI=1S/C41H48N2O8/c1-42-12-10-23-16-32(44-3)34(46-5)20-27(23)29(42)15-26-19-33(45-4)36(48-7)22-31(26)51-37-18-25-14-30-39-24(11-13-43(30)2)17-38(49-8)41(50-9)40(39)28(25)21-35(37)47-6/h16-22,29-30H,10-15H2,1-9H3/t29-,30-/m0/s1
InChIKey: ZCTJIMXXSXQXRI-KYJUHHDHSA-N
Reference
Biosynthesis of thalicarpine in Thalictrum minus
PubChem CID: 21470
CAS: 5373-42-2
LOTUS: LTS0215837
SuperNatural Ⅲ: SN0466908-05
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Thalictrum minus | Thalictrum | Ranunculaceae | Ranunculales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 696.8410000000001
TPSA？: 80.32000000000001
MolLogP？: 7.062900000000008
Number of H-Donors: 0
Number of H-Acceptors: 10
RingCount: 7
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Aspergillus fumigatus | Aspergillus fumigatus | Activity | nan | None | 10.1021/np50021a003 |
| Candida albicans | Candida albicans | Activity | nan | None | 10.1021/np50021a003 |
| Chlorocebus sabaeus | Vero C1008 | CC50 | 33000.0 | nM | 10.6019/CHEMBL4495565 |
| Cryptococcus neoformans | Cryptococcus neoformans | Activity | nan | None | 10.1021/np50021a003 |
| Enterococcus faecalis | Enterococcus faecalis | Activity | nan | None | 10.1021/np50021a003 |
| Escherichia coli | Escherichia coli | Activity | nan | None | 10.1021/np50021a003 |
| Homo sapiens | 786-0 | GI50 | 3515.6 | nM | None |
| Homo sapiens | A498 | GI50 | 7063.18 | nM | None |
| Homo sapiens | A549 | GI50 | 11857.69 | nM | None |
| Homo sapiens | ACHN | GI50 | 12852.87 | nM | None |
| Homo sapiens | BT-549 | GI50 | 6516.28 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 6223.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 8994.98 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 5754.4 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 15100.8 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 9099.13 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 10715.19 | nM | None |
| Homo sapiens | DU-145 | GI50 | 13963.68 | nM | None |
| Homo sapiens | EKVX | GI50 | 12941.96 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 7603.26 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 4830.59 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 5035.01 | nM | None |
| Homo sapiens | Histone deacetylase 6 | Inhibition | 8.82 | % | 10.6019/CHEMBL4808148 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | 33.61 | % | 10.6019/CHEMBL4808148 |
| Homo sapiens | HL-60 | GI50 | 2844.46 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 6295.06 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 10641.43 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 1778.28 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 2992.26 | nM | None |
| Homo sapiens | HT-29 | GI50 | 5662.39 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 10839.27 | nM | None |
| Homo sapiens | K562 | GI50 | 4875.28 | nM | None |
| Homo sapiens | KB | ED50 | 3.7 | ug ml-1 | 10.1021/np50022a010 |
| Homo sapiens | KM12 | GI50 | 5176.07 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 4528.98 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 7211.07 | nM | None |
| Homo sapiens | LXFL 529 | GI50 | 10990.06 | nM | None |
| Homo sapiens | M14 | GI50 | 1520.55 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 8871.56 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 9440.61 | nM | None |
| Homo sapiens | MCF7 | GI50 | 12246.16 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 4130.48 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 5164.16 | nM | None |
| Homo sapiens | MDA-N | GI50 | 4130.48 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 6251.73 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 11271.97 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 6576.58 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 12416.52 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 8394.6 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 9162.2 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 6886.52 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 10519.62 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 8298.51 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 10543.87 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 7430.19 | nM | None |
| Homo sapiens | PC-3 | GI50 | 4931.74 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 8035.26 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 3054.92 | nM | None |
| Homo sapiens | RXF 631 | GI50 | 5520.77 | nM | None |
| Homo sapiens | SF-268 | GI50 | 9977.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 10092.53 | nM | None |
| Homo sapiens | SF-539 | GI50 | 8279.42 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 10023.05 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 4017.91 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 3280.95 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 11641.26 | nM | None |
| Homo sapiens | SN12C | GI50 | 12387.97 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 7925.01 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 16710.91 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 7030.72 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 15452.54 | nM | None |
| Homo sapiens | SR | GI50 | 5081.59 | nM | None |
| Homo sapiens | SW-620 | GI50 | 7533.56 | nM | None |
| Homo sapiens | T47D | GI50 | 10139.11 | nM | None |
| Homo sapiens | TK-10 | GI50 | 3614.1 | nM | None |
| Homo sapiens | U-251 | GI50 | 3899.42 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 5128.61 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 6652.73 | nM | None |
| Homo sapiens | UO-31 | GI50 | 4655.86 | nM | None |
| Homo sapiens | XF498 | GI50 | 8974.29 | nM | None |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 reverse transcriptase | IC50 | 200.0 | ug.mL-1 | 10.1021/np50073a012 |
| Klebsiella pneumoniae | Klebsiella pneumoniae | Activity | nan | None | 10.1021/np50021a003 |
| Mus musculus | P388 | GI50 | 4236.43 | nM | None |
| Mus musculus | P388/ADR | GI50 | 8511.38 | nM | None |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | Activity | nan | None | 10.1021/np50021a003 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 2.917 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 3870.0 | nM | 10.6019/CHEMBL4495565 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | -0.18 | % | 10.6019/CHEMBL4495565 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | 14.48 | % | 10.21203/rs.3.rs-23951/v1 |
| Sporothrix schenckii | Sporothrix schenckii | Activity | nan | None | 10.1021/np50021a003 |
| Staphylococcus aureus | Staphylococcus aureus | Activity | nan | None | 10.1021/np50021a003 |
| Trichophyton mentagrophytes | Trichophyton mentagrophytes | Activity | nan | None | 10.1021/np50021a003 |
| None | ADMET | Selectivity index | 8.53 | None | 10.6019/CHEMBL4495565 |