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Compound Detail

CHEMBL938

SARALASIN
💊 Approved Drug
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💊 Approved Drug
CNCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H](C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)O)C(C)C)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL938
Name SARALASIN
Phase Approved
Structure Type BOTH
InChI Key PFGWGEPQIUAZME-NXSMLHPHSA-N
Therapeutic ✓ Yes

Known Names

1-sar-8-ala-angiotensin ii Sar-arg-val-tyr-val-his-pro-ala Saralasin Saralasina Saralasine
10
Targets
29
Activities
4
Assay Types
0
PK Parameters
20
Publications
5
Known Names

Molecular Properties

912.1
MW (Da)
-2.30
ALogP
12
HBA
13
HBD
355.1
PSA (Ų)
0.03
QED
3
Ro5 Violations
25
Rot. Bonds

Drug Information

Molecule Type Protein
First Approval 1982
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Year 1973

Extended Properties

Molecular Formula C42H65N13O10
MW 912.06
Aromatic Rings 2
Heavy Atoms 65
NP-Likeness -0.09

Activity Summary

IC50 16 meas. best 10.32
Ki 8 meas. best 9.82
EC50 3 meas. best 8.22
Kd 2 meas. best 9.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cavia porcellus
CHEMBL369
 IC50 10.32 10.32 0.0 1
Angiotensin II receptor
CHEMBL2094256
 IC50 10.18 10.18 0.1 1
Type-2 angiotensin II receptor
CHEMBL4607
 Ki 9.82 9.5533 0.1 3
Type-1 angiotensin II receptor
CHEMBL227
 Ki 9.77 9.6325 0.2 4
Unchecked
CHEMBL612545
 Ki 9.66 9.66 0.2 1
Angiotensin II receptor
CHEMBL2094112
 Kd 9.63 9.63 0.2 1
Type-1 angiotensin II receptor
CHEMBL227
 IC50 9.46 9.285 0.3 8
Type-2 angiotensin II receptor
CHEMBL4607
 IC50 9.35 9.17 0.5 3
Angiotensin II receptor (AT-1) type-1
CHEMBL2094250
 IC50 8.77 8.77 1.7 1
Oryctolagus cuniculus
CHEMBL374
 IC50 8.64 8.64 2.3 1
Type-1 angiotensin II receptor B
CHEMBL263
 IC50 8.62 8.62 2.4 1
Type-1 angiotensin II receptor A
CHEMBL329
 EC50 8.22 8.17 6.0 2
Type-1 angiotensin II receptor
CHEMBL227
 EC50 7.96 7.96 11.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cavia porcellus IC50 = 0.048 nM 10.32 The compound was tested for its inhibitory activity as antagonist of AI on guine... 1875337
Angiotensin II receptor IC50 = 0.066 nM 10.18 Inhibitory activity as antagonist of AII on guinea pig ileum 1875337
Type-2 angiotensin II receptor Ki = 0.15 nM 9.82 Displacement of radiolabeled saralasin from human AT2 receptor 18983139
Type-1 angiotensin II receptor Ki = 0.17 nM 9.77 Binding affinity to human AT1 receptor by radioligand displacement assay 23466604
Type-1 angiotensin II receptor Ki = 0.22 nM 9.66 Binding affinity to AT1 receptor (unknown origin) 25313325
Unchecked Ki = 0.22 nM 9.66 Displacement of 125I-[Sar1,Leu8] angiotensin-2 from rat type 1 angiotensin-2 rec... 26810314
Angiotensin II receptor Kd = 0.2323 nM 9.63 Antagonistic effect against Angiotensin II receptor in zona glomerulosa 3656348
Type-1 angiotensin II receptor Ki = 0.24 nM 9.62 Binding affinity to AT1 (unknown origin) assessed as inhibition constant 28849908
Type-1 angiotensin II receptor Ki = 0.33 nM 9.48 Displacement of radiolabeled saralasin from human AT1 receptor 18983139
Type-1 angiotensin II receptor IC50 = 0.35 nM 9.46 Binding affinity to human AT1 receptor by radioligand displacement assay 23466604
Type-2 angiotensin II receptor Ki = 0.38 nM 9.42 Binding affinity to type-2 angiotensin-2 receptor (unknown origin) 26810314
Type-2 angiotensin II receptor Ki = 0.38 nM 9.42 Binding affinity to AT2 receptor (unknown origin) 25313325
Type-1 angiotensin II receptor IC50 = 0.4 nM 9.4 Displacement of [125I][Sar1,Ile8]-AT2 from human recombinant AT1 receptor expres... 27876250
Type-1 angiotensin II receptor IC50 = 0.4 nM 9.4 Displacement of [125I][Sar, Ile]-ATII from human recombinant AT1 receptor expres... 26988801
Type-1 angiotensin II receptor IC50 = 0.41 nM 9.39 Inhibition of AT1 (unknown origin) 28849908
Type-2 angiotensin II receptor IC50 = 0.45 nM 9.35 Displacement of radiolabeled saralasin from human AT2 receptor 18983139
Type-2 angiotensin II receptor IC50 = 0.53 nM 9.28 Inhibition of human angiotensin II AT2 receptor 20875743
Type-1 angiotensin II receptor IC50 = 0.57 nM 9.24 Inhibition of human angiotensin II AT1 receptor 20875743
Type-1 angiotensin II receptor IC50 = 0.6 nM 9.22 Binding affinity to human angiotensin AT1 receptor by radioligand displacement a... 23582449
Type-1 angiotensin II receptor IC50 = 0.67 nM 9.17 Displacement of radiolabeled saralasin from human AT1 receptor 18983139

Literature References

PubMed DOI Target Context # Activities
2918497 10.1021/jm00123a002 Rattus norvegicus 6
3656348 10.1021/jm00393a006 Rattus norvegicus 5
25313325 10.1021/ml500278g Unchecked 3
3585907 10.1021/jm00389a021 Rattus norvegicus 3
18983139 10.1021/jm8007618 Type-1 angiotensin II receptor 2
28849908 10.1021/acschembio.7b00481 Type-1 angiotensin II receptor 2
23466604 10.1016/j.ejmech.2013.01.044 Type-1 angiotensin II receptor 2
18983139 10.1021/jm8007618 Type-2 angiotensin II receptor 2
3656348 10.1021/jm00393a006 Angiotensin II receptor 2
1875337 10.1021/jm00112a014 Angiotensin II receptor 2
1875337 10.1021/jm00112a014 Cavia porcellus 1
8515427 10.1021/jm00065a013 Angiotensin II receptor (AT-1) type-1 1
18588282 10.1021/jm701575k Type-1 angiotensin II receptor 1
20875743 10.1016/j.bmc.2010.07.034 Type-1 angiotensin II receptor 1
20875743 10.1016/j.bmc.2010.07.034 Type-2 angiotensin II receptor 1
23582449 10.1016/j.bmc.2013.03.016 Type-1 angiotensin II receptor 1
8230127 10.1021/jm00074a018 Oryctolagus cuniculus 1
8230127 10.1021/jm00074a018 Type-1 angiotensin II receptor B 1
25313325 10.1021/ml500278g Type-2 angiotensin II receptor 1
25313325 10.1021/ml500278g Type-1 angiotensin II receptor 1

Data from ChEMBL 36 via Core Engine