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2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid

AlkaPlorer ID: AK579338

Synonym: None

IUPAC Name: (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid

Structure

SMILES: CSCC[C@H](N=C(O)[C@H](CC1=CC=CC=C1)N=C(O)CN=C(O)CN=C(O)[C@@H](N)CC1=CC=C(O)C=C1)C(=O)O

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InChI: InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1

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InChIKey: YFGBQHOOROIVKG-FKBYEOEOSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Mytilus edulis Mytilus Mytilidae Mytilida Bivalvia Mollusca Metazoa Eukaryota

Properties Information

Molecule Weight: 573.6720000000005

TPSA？: 213.91

MolLogP？: 2.9056000000000006

Number of H-Donors: 7

Number of H-Acceptors: 8

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Cavia porcellus Activity 100.0 % 10.1021/jm00177a016
Cavia porcellus Cavia porcellus IC50 200.0 nM 10.1021/jm00118a005
Cavia porcellus Kappa opioid receptor IC50 10000.0 nM 10.1016/S0960-894X(01)81068-4
Cavia porcellus Kappa opioid receptor Ki 4467.0 nM 10.1016/j.bmcl.2006.05.060
Cavia porcellus Mu opioid receptor IC50 200.0 nM 10.1021/jm00142a002
Cavia porcellus Mu opioid receptor Ki 6.9 nM 10.1016/j.bmcl.2006.05.060
Cavia porcellus Nociceptin receptor Ki 277.0 nM 10.1016/j.bmcl.2006.05.060
Danio rerio Mu opioid receptor-like OR2 Ki 684.0 nM 10.1016/j.bmc.2017.02.052
Danio rerio Opioid receptor, delta 1b Ki 45.0 nM 10.1016/j.bmc.2017.02.052
Danio rerio Opioid receptor homologue Ki nan None 10.1016/j.bmc.2017.02.052
Homo sapiens Caco-2 Inhibition 3.2 % 10.1021/jm051026+
Homo sapiens Caco-2 Inhibition 4.2 % 10.1021/jm051026+
Homo sapiens Caco-2 Inhibition 6.4 % 10.1021/jm051026+
Homo sapiens Caco-2 Inhibition 8.4 % 10.1021/jm051026+
Homo sapiens Delta opioid receptor EC50 1.03 nM 10.1016/j.bmc.2011.11.047
Homo sapiens Delta opioid receptor EC50 1.03 nM 10.1016/j.bmcl.2009.03.099
Homo sapiens Delta opioid receptor EC50 47.0 nM 10.1016/j.bmcl.2007.01.092
Homo sapiens Delta opioid receptor IC50 6.4 nM 10.1021/acs.jmedchem.5b01170
Homo sapiens Delta opioid receptor Ki 1.1 nM 10.1016/j.bmcl.2006.05.060
Homo sapiens Delta opioid receptor Ki 2.0 nM 10.1016/j.bmcl.2007.01.092
Homo sapiens HBL Inhibition 0.4 % 10.1021/jm051026+
Homo sapiens HBL Inhibition 1.0 % 10.1021/jm051026+
Homo sapiens HBL Inhibition 4.5 % 10.1021/jm051026+
Homo sapiens HBL Inhibition 10.8 % 10.1021/jm051026+
Homo sapiens HeLa Inhibition 2.3 % 10.1021/jm051026+
Homo sapiens HeLa Inhibition 11.4 % 10.1021/jm051026+
Homo sapiens HeLa Inhibition 12.0 % 10.1021/jm051026+
Homo sapiens HeLa Inhibition 22.3 % 10.1021/jm051026+
Homo sapiens HEp-2 Inhibition 2.4 % 10.1021/jm051026+
Homo sapiens HEp-2 Inhibition 3.3 % 10.1021/jm051026+
Homo sapiens HEp-2 Inhibition 4.5 % 10.1021/jm051026+
Homo sapiens HEp-2 Inhibition 5.2 % 10.1021/jm051026+
Homo sapiens Histone deacetylase 6 Inhibition -7.67 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -7.34 % 10.6019/CHEMBL4808148
Homo sapiens HT-29 Inhibition 14.0 % 10.1021/jm051026+
Homo sapiens HT-29 Inhibition 15.9 % 10.1021/jm051026+
Homo sapiens HT-29 Inhibition 16.1 % 10.1021/jm051026+
Homo sapiens HT-29 Inhibition 19.3 % 10.1021/jm051026+
Homo sapiens Kappa opioid receptor Ki 10000.0 nM 10.1016/j.bmcl.2007.01.092
Homo sapiens MCF7 Inhibition 3.6 % 10.1021/jm051026+
Homo sapiens MCF7 Inhibition 4.1 % 10.1021/jm051026+
Homo sapiens MCF7 Inhibition 7.6 % 10.1021/jm051026+
Homo sapiens MCF7 Inhibition 15.4 % 10.1021/jm051026+
Homo sapiens Mu opioid receptor Activity 100.0 % 10.1016/j.bmcl.2021.127790
Homo sapiens Mu opioid receptor Activity nan None 10.1074/jbc.m703272200
Homo sapiens Mu opioid receptor EC50 620.0 nM 10.1016/j.bmcl.2007.01.092
Homo sapiens Mu opioid receptor IC50 13.0 nM 10.1021/acs.jmedchem.5b01170
Homo sapiens Mu opioid receptor Ki 19.0 nM 10.1016/j.bmcl.2007.01.092
Homo sapiens Regulator of G-protein signaling 4 Potency 8436.8 nM None
Homo sapiens SW-620 Inhibition 12.7 % 10.1021/jm051026+
Homo sapiens SW-620 Inhibition 15.3 % 10.1021/jm051026+
Homo sapiens SW-620 Inhibition 18.9 % 10.1021/jm051026+
Homo sapiens SW-620 Inhibition 19.1 % 10.1021/jm051026+
Mus musculus Delta opioid receptor IC50 13.0 nM 10.1021/jm00142a002
Mus musculus Mus musculus ED50 7e-07 M mouse-1 10.1016/S0960-894X(01)81068-4
Mus musculus Mus musculus IC50 13.0 nM 10.1021/jm00118a005
Rattus norvegicus Delta opioid receptor IC50 1.0 nM 10.1016/S0960-894X(01)81068-4
Rattus norvegicus Delta opioid receptor Ki 7.3 nM 10.1021/jm00118a005
Rattus norvegicus Mu opioid receptor EC50 304.0 nM 10.1021/jm4008592
Rattus norvegicus Mu opioid receptor EC50 309.03 nM 10.1021/jm4008592
Rattus norvegicus Mu opioid receptor Emax 205.3 % 10.1021/jm4008592
Rattus norvegicus Mu opioid receptor IC50 2.0 nM 10.1016/S0960-894X(01)81068-4
Rattus norvegicus Mu opioid receptor Ki 20.0 nM 10.1021/jm00043a007
Rattus norvegicus Mu opioid receptor Ki 27.5 nM 10.1021/jm00118a005
Rattus norvegicus Opioid receptor Activity 100.0 % 10.1021/jm00177a016
Rattus norvegicus Opioid receptor IC50 18.0 nM 10.1021/jm00143a007
Rattus norvegicus Opioid receptor IC50 90.0 nM 10.1021/jm00205a003
Rattus norvegicus Opioid receptor IC50 240.0 nM 10.1021/jm00143a007
Rattus norvegicus Opioid receptors; mu & delta Ratio 0.27 None 10.1021/jm00118a005
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.bmc.2019.115184
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 10.46 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 16.38 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -13.83 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.02 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.07 % 10.6019/CHEMBL4495565
None ADMET Stability nan % 10.1016/j.bmc.2019.115184
None Unchecked Ki 49500.0 nM 10.1021/jm00368a002
None Unchecked Ratio 0.065 None 10.1021/jm00118a005
None Unchecked Ratio 15.0 None 10.1021/jm00142a002
None Unchecked Ratio IC50 2.0 None 10.1021/acs.jmedchem.5b01170
None Unchecked Ratio Ki 9.5 None 10.1016/j.bmcl.2007.01.092

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT012032 CS(=O)CC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_25236
AKRT012525 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)N[C@@H](CCCCN)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_67706
AKRT012528 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](C(N)=O)C(C)C>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_74829
AKRT012529 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O 70675
AKRT012530 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_67533
AKRT012532 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O.N=C(N)NCCC[C@H](N)C(=O)O>>CSCC[C@H](N=C(O)[C@H](Cc1ccccc1)N=C(O)CN=C(O)CN=C(O)[C@@H](N)Cc1ccc(O)cc1)C(O)=N[C@@H](CCCNC(=N)N)C(=O)O MNXR131236
AKRT012533 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>CSCC[C@H](N)C(=O)O enzymemap_65295
AKRT012534 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>CSCC[C@H](NC(=O)[C@@H](N)Cc1ccccc1)C(=O)O 71483
AKRT012535 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CN)C(=O)O enzymemap_66654
AKRT012536 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CN)C(=O)O enzymemap_65446
AKRT012537 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>NC(Cc1ccc(O)cc1)C(O)=NCC(O)=NCC(=O)O MNXR132466
AKRT012538 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)O enzymemap_65295
AKRT012539 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)NCC(=O)NCC(=O)O 71483
AKRT012540 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)NCC(=O)O enzymemap_66654
AKRT012541 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)O enzymemap_65446
AKRT012542 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CCCCN)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_66094
AKRT012543 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CCCCN)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O.NCCCC[C@H](N)C(=O)O None
AKRT012545 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CCCNC(=N)N)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_66093
AKRT012546 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CCCNC(=N)N)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O.N=C(N)NCCC[C@H](N)C(=O)O None
AKRT012548 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCCCN)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_71972
AKRT012549 CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N)CCCCN)C(=O)O>>CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O enzymemap_71971