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name Structure Reference Source Properties Activities Metabolism

vindoline

AlkaPlorer ID: AK003117

Synonym: 'Vindoline', 'Vindolin', '(-)-Vindoline', 'NSC 91994'

IUPAC Name: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

Structure

SMILES: CC[C@]12C=CCN3CC[C@@]4(C5=C(C=C(OC)C=C5)N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC(C)=O)[C@@H]32

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InChI: InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1

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InChIKey: CXBGOBGJHGGWIE-ACSXSLCXSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Catharanthus roseus Catharanthus Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 456.5390000000002

TPSA？: 88.53999999999999

MolLogP？: 1.6412999999999998

Number of H-Donors: 1

Number of H-Acceptors: 8

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A498 GI50 101859.14 nM None
Homo sapiens A549 GI50 161808.0 nM None
Homo sapiens CAKI-1 GI50 15523.87 nM None
Homo sapiens CCRF-CEM GI50 131825.67 nM None
Homo sapiens COLO 205 GI50 184926.86 nM None
Homo sapiens DLD-1 GI50 199986.19 nM None
Homo sapiens DMS-114 GI50 140281.37 nM None
Homo sapiens DMS-273 GI50 139636.84 nM None
Homo sapiens EKVX GI50 151008.02 nM None
Homo sapiens HCC 2998 GI50 199986.19 nM None
Homo sapiens HCT-116 GI50 172186.86 nM None
Homo sapiens HCT-15 GI50 75335.56 nM None
Homo sapiens HL-60 GI50 89330.55 nM None
Homo sapiens HOP-18 GI50 199986.19 nM None
Homo sapiens HOP-62 GI50 170608.24 nM None
Homo sapiens HOP-92 GI50 46238.1 nM None
Homo sapiens HT-29 GI50 199986.19 nM None
Homo sapiens IGROV-1 GI50 185353.16 nM None
Homo sapiens K562 GI50 131219.99 nM None
Homo sapiens KM12 GI50 199986.19 nM None
Homo sapiens KM-20L2 GI50 100693.17 nM None
Homo sapiens LOX IMVI GI50 199986.19 nM None
Homo sapiens M19-MEL GI50 57543.99 nM None
Homo sapiens Malme-3M GI50 199986.19 nM None
Homo sapiens MCF7 GI50 147231.25 nM None
Homo sapiens MOLT-4 GI50 81283.05 nM None
Homo sapiens NCI/ADR-RES GI50 155596.56 nM None
Homo sapiens NCI-H226 GI50 132434.15 nM None
Homo sapiens NCI-H23 GI50 170608.24 nM None
Homo sapiens NCI-H322M GI50 199986.19 nM None
Homo sapiens NCI-H460 GI50 177418.95 nM None
Homo sapiens NCI-H522 GI50 97949.0 nM None
Homo sapiens OVCAR-3 GI50 102093.95 nM None
Homo sapiens OVCAR-4 GI50 35399.73 nM None
Homo sapiens OVCAR-5 GI50 199986.19 nM None
Homo sapiens OVCAR-8 GI50 19453.6 nM None
Homo sapiens RPMI-8226 GI50 93756.2 nM None
Homo sapiens RXF 393 GI50 96827.79 nM None
Homo sapiens SF-268 GI50 137720.95 nM None
Homo sapiens SF-295 GI50 152054.75 nM None
Homo sapiens SF-539 GI50 199986.19 nM None
Homo sapiens SK-MEL-2 GI50 182389.57 nM None
Homo sapiens SK-MEL-28 GI50 199986.19 nM None
Homo sapiens SK-MEL-5 GI50 99540.54 nM None
Homo sapiens SK-OV-3 GI50 199986.19 nM None
Homo sapiens SN12C GI50 183231.44 nM None
Homo sapiens SN12K1 GI50 192752.49 nM None
Homo sapiens SNB-19 GI50 199986.19 nM None
Homo sapiens SNB-75 GI50 51286.14 nM None
Homo sapiens SNB-78 GI50 195433.95 nM None
Homo sapiens SW-620 GI50 199986.19 nM None
Homo sapiens U-251 GI50 199986.19 nM None
Homo sapiens UACC-257 GI50 171790.84 nM None
Homo sapiens UACC-62 GI50 142889.4 nM None
Homo sapiens UO-31 GI50 59020.11 nM None
Homo sapiens XF498 GI50 172186.86 nM None
Mus musculus MIN6 EC50 50200.0 nM 10.1016/j.bmcl.2016.09.064
Mus musculus P388 GI50 14521.12 nM None
Mus musculus P388/ADR GI50 95279.62 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004523 CC(=O)[CoA].CC[C@]12C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1O)[C@@H]32>>CC[C@]12C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC(C)=O)[C@@H]32 R03230
AKRT007318 CCC1=CC2CN3CCc4c([nH]c5ccccc45)[C@](C(=O)OC)(C2)[C@@H]13.CC[C@]12C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC(C)=O)[C@@H]32>>CCC1=C[C@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1 R05858
AKRT007319 CCC1=C[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@](C(=O)OC)(C2)[C@@H]13.CC[C@]12C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC(C)=O)[C@@H]32>>CCC1=C[C@H]2C[N+](CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CC[N+]6CC[C@]43[C@@H]65)C2)C1 RXN-8201