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(11S,14S)-Cyclo-(L-Trp-L-Phe)

AlkaPlorer ID: AK015317

Synonym: '(3S,6S)-3-Benzyl-6-(1H-indol-3-ylmethyl)-2,5-piperazinedione', 'Cyclo-l-Trp-l-Phe', 'Cyclo(phenylalanyltryptophyl)'

IUPAC Name: (3S,6S)-3-benzyl-6-(1H-indol-3-ylmethyl)piperazine-2,5-dione

Structure

SMILES: OC1=N[C@@H](CC2=CNC3=CC=CC=C23)C(O)=N[C@H]1CC1=CC=CC=C1

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InChI: InChI=1S/C20H19N3O2/c24-19-17(10-13-6-2-1-3-7-13)22-20(25)18(23-19)11-14-12-21-16-9-5-4-8-15(14)16/h1-9,12,17-18,21H,10-11H2,(H,22,25)(H,23,24)/t17-,18-/m0/s1

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InChIKey: CUVKAUWOMPJEMI-ROUUACIJSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Aspergillus sydowii Aspergillus Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 333.3910000000001

TPSA？: 80.97

MolLogP？: 3.616900000000002

Number of H-Donors: 3

Number of H-Acceptors: 2

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A2780 IC50 100000.0 nM 10.1016/j.bmcl.2012.04.119
Homo sapiens Calpain 1 Inhibition 0.0 % 10.1016/j.bmcl.2005.04.031
Homo sapiens Chromobox protein homolog 1 Potency 70794.6 nM None
Homo sapiens K562 IC50 100000.0 nM 10.1016/j.bmcl.2012.04.119
Homo sapiens TAR DNA-binding protein 43 Potency 6309.6 nM None
None Radical scavenging activity Activity nan None 10.1021/np200374j

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT005292 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H]1Cc1ccccc1>>CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC1=O enzymemap_39830
AKRT005293 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H]1Cc1ccccc1>>CC(C)=CCc1cccc2c(C[C@@H]3NC(=O)[C@H](Cc4ccccc4)NC3=O)c[nH]c12 enzymemap_39883
AKRT005297 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2ccccc2)C(=O)N[C@H]1Cc1c[nH]c2ccccc12>>CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC1=O None
AKRT005298 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2ccccc2)C(=O)N[C@H]1Cc1c[nH]c2ccccc12>>CC(C)=CCc1cccc2c(C[C@@H]3NC(=O)[C@H](Cc4ccccc4)NC3=O)c[nH]c12 None
AKRT014733 C[SAH].O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H]1Cc1ccccc1>>CN1C(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@@H]1Cc1ccccc1 R12414
AKRT019752 N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O.N[C@@H](Cc1ccccc1)C(=O)O>>O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H]1Cc1ccccc1 R12413