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Protirelin

AlkaPlorer ID: AK076820

Synonym: None

IUPAC Name: (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide

Structure

SMILES: N=C(O)[C@@H]1CCCN1C(=O)[C@H](CC1=CN=CN1)N=C(O)[C@@H]1CCC(O)=N1

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InChI: InChI=1S/C16H22N6O4/c17-14(24)12-2-1-5-22(12)16(26)11(6-9-7-18-8-19-9)21-15(25)10-3-4-13(23)20-10/h7-8,10-12H,1-6H2,(H2,17,24)(H,18,19)(H,20,23)(H,21,25)/t10-,11-,12-/m0/s1

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InChIKey: XNSAINXGIQZQOO-SRVKXCTJSA-N

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Properties Information

Molecule Weight: 362.39000000000016

TPSA？: 158.25

MolLogP？: 0.9224699999999996

Number of H-Donors: 5

Number of H-Acceptors: 5

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Adhesion G-protein coupled receptor F1 %Inhib (Mean) -32.16 % 10.6019/CHEMBL5209801
Homo sapiens Adhesion G-protein coupled receptor F1 %Max (Mean) 5.283 % 10.6019/CHEMBL5209801
Homo sapiens Alpha-2a adrenergic receptor %Inhib (Mean) 4.4 % 10.6019/CHEMBL5209801
Homo sapiens Alpha-2a adrenergic receptor %Max (Mean) 19.1 % 10.6019/CHEMBL5209801
Homo sapiens Apelin receptor %Inhib (Mean) -13.89 % 10.6019/CHEMBL5209801
Homo sapiens Apelin receptor %Max (Mean) -1.332 % 10.6019/CHEMBL5209801
Homo sapiens Beta-2 adrenergic receptor %Inhib (Mean) -8.16 % 10.6019/CHEMBL5209801
Homo sapiens Beta-2 adrenergic receptor %Max (Mean) -2.97 % 10.6019/CHEMBL5209801
Homo sapiens Bromodomain-containing protein 4 Delta TM 0.08717 C None
Homo sapiens C5a anaphylatoxin chemotactic receptor %Inhib (Mean) -44.67 % 10.6019/CHEMBL5209801
Homo sapiens C5a anaphylatoxin chemotactic receptor %Max (Mean) -0.5676 % 10.6019/CHEMBL5209801
Homo sapiens Caco-2 Papp 0.147 10^-6 cm/s 10.1016/j.bmc.2007.04.042
Homo sapiens Caco-2 Stability 5.0 % 10.1016/j.bmc.2007.04.042
Homo sapiens Caco-2 T1/2 0.05 hr 10.1016/j.bmc.2007.04.042
Homo sapiens Casein kinase I delta Delta TM 0.02561 C None
Homo sapiens C-X3-C chemokine receptor 1 %Inhib (Mean) -12.71 % 10.6019/CHEMBL5209801
Homo sapiens C-X3-C chemokine receptor 1 %Max (Mean) -2.745 % 10.6019/CHEMBL5209801
Homo sapiens Cyclin-dependent kinase 2 Delta TM 0.09109 C None
Homo sapiens Fibroblast Growth Rate 0.0 None 10.6019/CHEMBL4689842
Homo sapiens Fibroblast Growth Rate 1.0 None 10.6019/CHEMBL4689842
Homo sapiens Fibroblast growth factor receptor 3 Delta TM 0.1223 C None
Homo sapiens Glucagon-like peptide 1 receptor %Inhib (Mean) -31.32 % 10.6019/CHEMBL5209801
Homo sapiens Glucagon-like peptide 1 receptor %Max (Mean) 0.53 % 10.6019/CHEMBL5209801
Homo sapiens Glucose-dependent insulinotropic receptor %Inhib (Mean) -36.62 % 10.6019/CHEMBL5209801
Homo sapiens Glucose-dependent insulinotropic receptor %Max (Mean) 8.743 % 10.6019/CHEMBL5209801
Homo sapiens Glycogen synthase kinase-3 beta Delta TM -0.6781 C None
Homo sapiens G-protein coupled receptor 120 %Inhib (Mean) -39.5 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 120 %Max (Mean) -1.7 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 35 %Inhib (Mean) -12.5 % 10.6019/CHEMBL5209801
Homo sapiens G-protein coupled receptor 35 %Max (Mean) 10.82 % 10.6019/CHEMBL5209801
Homo sapiens HEK-293T Growth Rate 0.0 None 10.6019/CHEMBL4689842
Homo sapiens HEK-293T Growth Rate 1.0 None 10.6019/CHEMBL4689842
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 0.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Lipoxin A4 receptor %Inhib (Mean) -27.04 % 10.6019/CHEMBL5209801
Homo sapiens Lipoxin A4 receptor %Max (Mean) -3.23 % 10.6019/CHEMBL5209801
Homo sapiens MAP kinase ERK2 Delta TM 0.2422 C None
Homo sapiens Peregrin Delta TM 0.2166 C None
Homo sapiens Plasma T1/2 0.03333 hr 10.1016/j.bmc.2015.07.022
Homo sapiens Serine/threonine-protein kinase Aurora-A Delta TM 0.1767 C None
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 %Inhib (Mean) 7.4 % 10.6019/CHEMBL5209801
Homo sapiens Sphingosine 1-phosphate receptor Edg-1 %Max (Mean) 6.18 % 10.6019/CHEMBL5209801
Homo sapiens Thyrotropin-releasing hormone receptor EC50 3.0 nM 10.1016/j.bmc.2006.09.045
Homo sapiens Thyrotropin-releasing hormone receptor Ki 20.0 nM 10.1016/j.bmc.2006.09.045
Homo sapiens Transcription intermediary factor 1-alpha Delta TM -0.3853 C None
Homo sapiens Type-1 angiotensin II receptor %Inhib (Mean) -36.11 % 10.6019/CHEMBL5209801
Homo sapiens Type-1 angiotensin II receptor %Max (Mean) 5.701 % 10.6019/CHEMBL5209801
Homo sapiens Tyrosine-protein kinase ABL Delta TM -0.164 C None
Homo sapiens U2OS Growth Rate 0.0 None 10.6019/CHEMBL4689842
Homo sapiens U2OS Growth Rate 1.0 None 10.6019/CHEMBL4689842
Mus musculus Mus musculus Activity nan None 10.1016/0960-894X(96)00478-7
Mus musculus Mus musculus Inhibition 51.1 % 10.1016/j.bmc.2015.07.022
Mus musculus Mus musculus Inhibition 51.14 % 10.1016/j.ejmech.2016.01.038
Mus musculus Mus musculus Mean latency 20.85 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 25.76 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 28.87 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 32.69 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 33.57 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 37.97 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 43.08 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 46.0 s 10.1021/jm00015a009
Mus musculus Mus musculus Mean latency 50.59 s 10.1021/jm00015a009
Mus musculus Mus musculus RRT 34.1 s 10.1021/jm00111a014
Mus musculus Mus musculus RRT 40.8 s 10.1021/jm00111a013
Mus musculus Mus musculus RRT 40.8 s 10.1021/jm00111a014
Mus musculus Mus musculus RRT 44.0 s 10.1021/jm980333v
Mus musculus Mus musculus RRT 100.1 s 10.1021/jm00111a014
Mus musculus Mus musculus RRT 173.0 s 10.1021/jm980333v
Mus musculus Mus musculus Sleeping time 24.8 min 10.1021/jm00159a015
Mus musculus Mus musculus Sleeping time 26.0 min 10.1021/jm020531t
Mus musculus Mus musculus Sleeping time 377.0 s 10.1021/jm980333v
Mus musculus Mus musculus Sleeping time 663.0 s 10.1021/jm980333v
Mus musculus Mus musculus SMT 40.9 s 10.1021/jm00111a013
Mus musculus Mus musculus SMT 40.9 s 10.1021/jm00111a014
Mus musculus Mus musculus SMT 48.2 s 10.1021/jm00111a014
Mus musculus Mus musculus SMT 118.2 s 10.1021/jm00111a014
Mus musculus Mus musculus ST 70.7 s 10.1021/jm00111a014
Mus musculus Mus musculus ST 73.2 s 10.1021/jm00111a014
Mus musculus Mus musculus ST 83.1 s 10.1021/jm00111a014
Mus musculus Mus musculus SVT 43.4 % 10.1021/jm00111a014
Mus musculus Mus musculus SVT 43.4 None 10.1021/jm00111a013
Mus musculus Mus musculus SVT 47.1 % 10.1021/jm00111a014
Mus musculus Mus musculus SVT 83.8 % 10.1021/jm00111a014
Mus musculus Mus musculus SVT nan None 10.1021/jm00111a013
Mus musculus Thyrotropin-releasing hormone-degrading ectoenzyme Drug degradation 75.0 % 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone-degrading ectoenzyme Drug degradation 80.0 % 10.1016/j.bmc.2015.07.022
Mus musculus Thyrotropin-releasing hormone receptor Activity 334.0 cpm 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor Activity 393.0 cpm 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor Activity 513.46 cpm 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor Activity 719.25 cpm 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor EC50 0.49 nM 10.1016/s0960-894x(98)00567-8
Mus musculus Thyrotropin-releasing hormone receptor EC50 0.68 nM 10.1021/jm960053k
Mus musculus Thyrotropin-releasing hormone receptor EC50 1.0 nM 10.1016/j.bmc.2015.07.022
Mus musculus Thyrotropin-releasing hormone receptor EC50 1.0 nM 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor EC50 3.2 nM 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor IC50 2.6 nM 10.1016/j.bmc.2015.07.022
Mus musculus Thyrotropin-releasing hormone receptor IC50 26.0 nM 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor Ki 10.0 nM 10.1021/jm960053k
Mus musculus Thyrotropin-releasing hormone receptor Ki 23.0 nM 10.1016/s0960-894x(98)00567-8
Mus musculus Thyrotropin-releasing hormone receptor 2 EC50 0.5 nM 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor 2 EC50 0.52 nM 10.1016/j.bmc.2015.07.022
Mus musculus Thyrotropin-releasing hormone receptor 2 EC50 3.1 nM 10.1016/j.ejmech.2016.01.038
Mus musculus Thyrotropin-releasing hormone receptor 2 IC50 7.0 nM 10.1016/j.bmc.2015.07.022
Mus musculus Thyrotropin-releasing hormone receptor 2 IC50 7.0 nM 10.1016/j.ejmech.2016.01.038
Plasmodium falciparum Plasmodium falciparum Potency 3013.1 nM None
Rattus norvegicus Plasma Cp 4.83 ng/ml 10.1016/j.bmc.2015.07.022
Rattus norvegicus Plasma Cp 6.06 ng/ml 10.1016/j.bmc.2015.07.022
Rattus norvegicus Plasma Cp 6.8 ng/ml 10.1016/j.bmc.2015.07.022
Rattus norvegicus Rattus norvegicus Activity 100.0 % 10.1021/jm00159a015
Rattus norvegicus Rattus norvegicus ED50 113.0 mg.kg-1 10.1021/jm00159a015
Rattus norvegicus Rattus norvegicus ED50 113.0 mg.kg-1 10.1021/jm00372a006
Rattus norvegicus Rattus norvegicus Inhibition 40.0 % 10.1021/jm00159a015
Rattus norvegicus Rattus norvegicus Inhibition 40.0 % 10.1021/jm00372a006
Rattus norvegicus Rattus norvegicus Maximal change 394.0 % 10.1021/jm020531t
Rattus norvegicus Rattus norvegicus Relative activity 100.0 % 10.1021/jm00136a003
Rattus norvegicus Rattus norvegicus Serum TSH 59.1 ug 100ml-1 10.1021/jm00170a014
Rattus norvegicus Rattus norvegicus Serum TSH 114.7 ug 100ml-1 10.1021/jm00170a014
Rattus norvegicus Rattus norvegicus Serum TSH 350.8 ug 100ml-1 10.1021/jm00170a014
Rattus norvegicus Sigma opioid receptor NT nan None 10.1021/jm980333v
Rattus norvegicus Thyrotropin-releasing hormone receptor EC50 3.0 nM 10.1021/jm0505462
Rattus norvegicus Thyrotropin-releasing hormone receptor Ki 20.0 nM 10.1021/jm0505462
Rattus norvegicus Thyrotropin-releasing hormone receptor Ki 42.3 nM 10.1021/jm020531t
Rattus norvegicus Thyrotropin-releasing hormone receptor 2 EC50 3.0 nM 10.1016/j.bmc.2006.09.045
Rattus norvegicus Thyrotropin-releasing hormone receptor 2 EC50 3.0 nM 10.1021/jm0505462
Rattus norvegicus Thyrotropin-releasing hormone receptor 2 IC50 23.0 nM 10.1021/np070658r
Rattus norvegicus Thyrotropin-releasing hormone receptor 2 IC50 23000.0 nM 10.1021/np0706567
Rattus norvegicus Thyrotropin-releasing hormone receptor 2 Ki 10.0 nM 10.1016/j.bmc.2006.09.045
Rattus norvegicus Thyrotropin-releasing hormone receptor 2 Ki 10.0 nM 10.1021/jm0505462
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.04354 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index 0.1003 None 10.1101/2020.04.03.023846
Sus scrofa Thyrotropin releasing hormone degrading enzyme Activity 2.54 U/mg None
Sus scrofa Thyrotropin releasing hormone degrading enzyme Km 35000.0 nM None
Sus scrofa Thyrotropin releasing hormone degrading enzyme Vmax 2.63 U/mg None
Sus scrofa Thyrotropin releasing hormone degrading enzyme Vmax/Km 0.08 U/mg/uM None
None ADMET K''IAM 0.51 None 10.1021/jm020531t
None ADMET T1/2 0.1833 hr 10.1021/jm020531t
None ADMET T1/2 0.2667 hr 10.1021/jm020531t
None No relevant target CLogP -4.37 None 10.1021/jm020531t
None No relevant target CLogP -0.27 None 10.1021/jm020531t
None No relevant target LogP -1.74 None 10.1021/jm020531t
None Unchecked Ac50 3.162 uM None
None Unchecked Ac50 3.981 uM None
None Unchecked Ac50 28.18 uM None
None Unchecked AC50 3162.3 nM None
None Unchecked AC50 3981.1 nM None
None Unchecked AC50 28190.0 nM None
None Unchecked Activity 100.0 % 10.1021/jm00372a006
None Unchecked Ratio 1.0 None 10.1021/jm00170a014
None Unchecked Ratio EC50 1.0 None 10.1016/j.ejmech.2016.01.038
None Unchecked Ratio EC50 1.9 None 10.1016/j.bmc.2015.07.022
None Unchecked Ratio EC50 2.0 None 10.1016/j.ejmech.2016.01.038
None Unchecked Ratio IC50 3.7 None 10.1016/j.ejmech.2016.01.038
None Unchecked Selectivity 2.0 None 10.1021/jm0505462

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT016851 NC(=O)CC[C@H](N)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N1CCC[C@H]1C(N)=O>>NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1 enzymemap_33256
AKRT017203 NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1>>NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)Cc1cnc[nH]1 enzymemap_68215
AKRT017204 NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1>>O=C1CC[C@@H](C(=O)N[C@@H](Cc2cnc[nH]2)C(=O)N2CCC[C@H]2C(=O)O)N1 enzymemap_69374
AKRT017205 NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1>>O=C1CC[C@@H](C(=O)O)N1 enzymemap_68215