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tomatine

AlkaPlorer ID: AK001648

Synonym: '', 'Lycopersicin', '(3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside', 'Tomatine', "A''-Tomatidine", 'Tomatin', 'lycopersicin', 'alpha-tomatine'

IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Structure

SMILES: C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

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InChI: InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1

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InChIKey: REJLGAUYTKNVJM-SGXCCWNXSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 1034.2000000000005

TPSA？: 337.86

MolLogP？: -2.6972999999999807

Number of H-Donors: 13

Number of H-Acceptors: 22

RingCount: 10

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens 786-0 GI50 1288.25 nM None
Homo sapiens A498 GI50 1874.99 nM None
Homo sapiens A549 GI50 1545.25 nM None
Homo sapiens ACHN GI50 1710.02 nM None
Homo sapiens BT-549 GI50 2365.92 nM None
Homo sapiens CAKI-1 GI50 753.36 nM None
Homo sapiens CCRF-CEM GI50 2517.68 nM None
Homo sapiens COLO 205 GI50 1999.86 nM None
Homo sapiens DU-145 GI50 1640.59 nM None
Homo sapiens EKVX GI50 835.6 nM None
Homo sapiens HCC 2998 GI50 993.12 nM None
Homo sapiens HCT-116 GI50 1702.16 nM None
Homo sapiens HCT-15 GI50 2477.42 nM None
Homo sapiens HL-60 GI50 2483.13 nM None
Homo sapiens HOP-62 GI50 1633.05 nM None
Homo sapiens HOP-92 GI50 1990.67 nM None
Homo sapiens Hs-578T GI50 1640.59 nM None
Homo sapiens HT-29 GI50 1914.26 nM None
Homo sapiens IGROV-1 GI50 729.46 nM None
Homo sapiens K562 GI50 2735.27 nM None
Homo sapiens KM12 GI50 1976.97 nM None
Homo sapiens LOX IMVI GI50 2172.7 nM None
Homo sapiens M14 GI50 1432.19 nM None
Homo sapiens Malme-3M GI50 605.34 nM None
Homo sapiens MCF7 GI50 2322.74 nM None
Homo sapiens MDA-MB-231 GI50 1300.17 nM None
Homo sapiens MDA-MB-435 GI50 1409.29 nM None
Homo sapiens MDA-N GI50 558.47 nM None
Homo sapiens MOLT-4 GI50 2409.91 nM None
Homo sapiens NCI/ADR-RES GI50 1896.71 nM None
Homo sapiens NCI-H226 GI50 1945.36 nM None
Homo sapiens NCI-H23 GI50 1651.96 nM None
Homo sapiens NCI-H322M GI50 1729.82 nM None
Homo sapiens NCI-H460 GI50 2182.73 nM None
Homo sapiens NCI-H522 GI50 1621.81 nM None
Homo sapiens OVCAR-3 GI50 2027.68 nM None
Homo sapiens OVCAR-4 GI50 1393.16 nM None
Homo sapiens OVCAR-5 GI50 1235.95 nM None
Homo sapiens OVCAR-8 GI50 2238.72 nM None
Homo sapiens PC-3 GI50 719.45 nM None
Homo sapiens RPMI-8226 GI50 765.6 nM None
Homo sapiens RXF 393 GI50 1803.02 nM None
Homo sapiens SF-268 GI50 1552.39 nM None
Homo sapiens SF-295 GI50 1047.13 nM None
Homo sapiens SF-539 GI50 1555.97 nM None
Homo sapiens SK-MEL-2 GI50 1682.67 nM None
Homo sapiens SK-MEL-28 GI50 1258.93 nM None
Homo sapiens SK-MEL-5 GI50 2233.57 nM None
Homo sapiens SK-OV-3 GI50 1610.65 nM None
Homo sapiens SN12C GI50 1425.61 nM None
Homo sapiens SNB-19 GI50 1235.95 nM None
Homo sapiens SNB-75 GI50 1862.09 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 96.72 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 100.28 % 10.1124/mol.112.084152
Homo sapiens SR GI50 2415.46 nM None
Homo sapiens SW-620 GI50 2041.74 nM None
Homo sapiens T47D GI50 1972.42 nM None
Homo sapiens TK-10 GI50 1541.7 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1678.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1883.7 nM None
Homo sapiens U-251 GI50 1018.59 nM None
Homo sapiens UACC-257 GI50 2123.24 nM None
Homo sapiens UACC-62 GI50 1011.58 nM None
Homo sapiens UO-31 GI50 1422.33 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Panagrellus redivivus Panagrellus redivivus ED50 50.0 ug ml-1 10.1146/annurev.phyto.40.032602.130045
Trichomonas vaginalis Trichomonas vaginalis Inhibition 103.0 % 10.1016/j.ejmech.2017.11.029
None Unchecked Potency 446.7 nM None
None Unchecked Potency 1000.0 nM None
None Unchecked Potency 4466.8 nM None
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 25118.9 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT014035 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C RXN18C3-12
AKRT014037 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C>>C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C RXN18C3-15
AKRT014038 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C>>C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C RXN18C3-16
AKRT014039 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C>>C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C RXN18C3-14
AKRT014040 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C>>OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O RXN18C3-14
AKRT014041 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C>>OC[C@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O RXN18C3-15
AKRT014042 C[C@H]1CC[C@]2(NC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C>>O[C@H]1OC[C@@H](O)[C@H](O)[C@H]1O RXN18C3-16