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Tryprostatin B

AlkaPlorer ID: AK001134

Synonym: None

IUPAC Name: (3S,8aS)-3-[[2-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Structure

SMILES: CC(C)=CCC1=C(C[C@@H]2N=C(O)[C@@H]3CCCN3C2=O)C2=CC=CC=C2N1

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InChI: InChI=1S/C21H25N3O2/c1-13(2)9-10-17-15(14-6-3-4-7-16(14)22-17)12-18-21(26)24-11-5-8-19(24)20(25)23-18/h3-4,6-7,9,18-19,22H,5,8,10-12H2,1-2H3,(H,23,25)/t18-,19-/m0/s1

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InChIKey: GLWYBXPXOSKQAW-OALUTQOASA-N

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Properties Information

Molecule Weight: 351.45000000000005

TPSA？: 68.69

MolLogP？: 3.5488000000000017

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A2780 IC50 82800.0 nM 10.1016/j.bmcl.2012.04.119
Homo sapiens A2780 IC50 85900.0 nM 10.1016/j.bmcl.2012.04.119
Homo sapiens ATP-binding cassette sub-family G member 2 Inhibition nan % 10.1016/j.bmcl.2016.11.013
Homo sapiens BT-549 GI50 58200.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens CCRF-CEM GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens COLO 205 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens DU-145 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens EKVX GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens HOP-92 GI50 43100.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens HT-29 GI50 nan None 10.1016/j.bmc.2008.02.050
Homo sapiens IGROV-1 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens K562 GI50 56100.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens K562 IC50 21100.0 nM 10.1016/j.bmcl.2012.04.119
Homo sapiens K562 IC50 41000.0 nM 10.1021/np800700e
Homo sapiens KB Activity nan None 10.1021/np800700e
Homo sapiens LOX IMVI GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens MCF7 Activity nan None 10.1021/np800700e
Homo sapiens MCF7 Cell survival 66.7 % 10.1021/jm0155953
Homo sapiens MCF7 Cell survival 88.2 % 10.1021/jm0155953
Homo sapiens MCF7 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens MCF7 Inhibition 66.7 % 10.1016/j.bmc.2008.02.050
Homo sapiens MCF7 Inhibition 88.2 % 10.1016/j.bmc.2008.02.050
Homo sapiens MOLT-4 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens NCI-H520 Cell survival 60.5 % 10.1021/jm0155953
Homo sapiens NCI-H520 Cell survival 77.6 % 10.1021/jm0155953
Homo sapiens OVCAR-3 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens PC-3 Cell survival 68.9 % 10.1021/jm0155953
Homo sapiens PC-3 Cell survival 95.5 % 10.1021/jm0155953
Homo sapiens PC-3 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens PC-3 Inhibition 68.9 % 10.1016/j.bmc.2008.02.050
Homo sapiens PC-3 Inhibition 95.5 % 10.1016/j.bmc.2008.02.050
Homo sapiens RPMI-8226 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens SR GI50 50600.0 nM 10.1016/j.bmc.2008.02.050
Homo sapiens UO-31 GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
Rattus norvegicus PC-12 Activity nan None 10.1021/np800700e
None NON-PROTEIN TARGET GI50 100000.0 nM 10.1016/j.bmc.2008.02.050
None NON-PROTEIN TARGET IC50 18800.0 nM 10.1016/j.bmcl.2012.04.119
None NON-PROTEIN TARGET Inhibition 60.5 % 10.1016/j.bmc.2008.02.050
None NON-PROTEIN TARGET Inhibition 77.6 % 10.1016/j.bmc.2008.02.050
None NON-PROTEIN TARGET MIC 4400.0 nM 10.1016/j.bmcl.2012.04.119
None Unchecked IC50 700000.0 nM 10.1016/j.bmc.2008.02.050
None Unchecked MIC 4400.0 nM 10.1016/j.ejmech.2019.03.025

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT005282 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12>>CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O RXN-14418
AKRT005315 CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O>>CC(C)=CCc1[nH]c2cc(O)ccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O RXN-14413
AKRT005316 CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O>>CC(C)=C[C@H]1c2[nH]c3ccccc3c2C[C@H]2C(=O)N3CCC[C@H]3C(=O)N21 RXN-14416