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Compound Detail

CHEMBL419667

RELCOVAPTAN
🧪 Phase II
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🧪 Phase II
COc1ccc(S(=O)(=O)N2c3ccc(Cl)cc3[C@](O)(c3ccccc3Cl)[C@@H]2C(=O)N2CCC[C@H]2C(N)=O)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL419667
Name RELCOVAPTAN
Phase Phase II
Structure Type MOL
InChI Key CEBYCSRFKCEUSW-NAYZPBBASA-N

Known Names

Relcovaptan SR 49059 Sr-49059 SR49059 TDI 0134 TDI-0134
5
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names
2
Mechanisms

Molecular Properties

620.5
MW (Da)
3.30
ALogP
7
HBA
2
HBD
139.5
PSA (Ų)
0.41
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vaptan

Extended Properties

Molecular Formula C28H27Cl2N3O7S
MW 620.51
Aromatic Rings 3
Heavy Atoms 41
NP-Likeness -0.46

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Vasopressin V1a receptor antagonist ANTAGONIST Vasopressin V1a receptor ✓ ✓
Oxytocin receptor antagonist ANTAGONIST Oxytocin receptor ✓ ✓

Activity Summary

Ki 12 meas. best 9.72
EC50 1 meas. best 5.32
IC50 1 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vasopressin V1a receptor
CHEMBL1889
 Ki 9.72 9.1511 0.2 9
Vasopressin V1a receptor
CHEMBL2868
 Ki 8.85 8.85 1.4 1
Vasopressin V1a receptor
CHEMBL1889
 IC50 7.89 7.89 13.0 1
Vasopressin V2 receptor
CHEMBL1790
 Ki 6.75 6.75 178.0 1
Vasopressin V2 receptor
CHEMBL3766
 Ki 6.54 6.54 285.0 1
Free fatty acid receptor 4
CHEMBL5339
 EC50 5.32 5.32 4775.2 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vasopressin V1a receptor Ki = 0.19 nM 9.72 Inhibition of human vasopressin V1a receptor expressed in COS7 cells by HTRF-FRE... 17850055
Vasopressin V1a receptor Ki = 0.53 nM 9.28 Binding affinity at cloned human Vasopressin V1a receptor stably expressed in CH... 12036368
Vasopressin V1a receptor Ki = 0.52 nM 9.28 Inhibition of human vasopressin V1a receptor expressed in COS7 cells by HTRF-FRE... 17850055
Vasopressin V1a receptor Ki = 0.53 nM 9.28 Displacement of [125I]OH-Phpa-LVA from human V1A receptor expressed in CHO cells... 30395477
Vasopressin V1a receptor Ki = 0.7 nM 9.15 Inhibition of human vasopressin V1a receptor expressed in CHO cells by polarisat... 17850055
Vasopressin V1a receptor Ki = 0.85 nM 9.07 Inhibition of human vasopressin V1a receptor expressed in COS7 cells by HTRF-FRE... 17850055
Vasopressin V1a receptor Ki = 0.9 nM 9.05 Displacement of [Se-Se]-AVP from human V1A receptor expressed in CHO cells after... 30395477
Vasopressin V1a receptor Ki = 1.43 nM 8.85 Binding affinity at Vasopressin V1a receptor, performed using [3H]AVP on rat liv... 12036368
Vasopressin V1a receptor Ki = 1.48 nM 8.83 Inhibition of human vasopressin V1a receptor expressed in CHO cells by polarisat... 17850055
Vasopressin V1a receptor Ki = 2.0 nM 8.7 Binding affinity to vasopressin V1a receptor 7807119
Vasopressin V1a receptor IC50 = 13.0 nM 7.89 Antagonist activity at human V1A receptor expressed in CHO cells assessed as inh... 21885275
Vasopressin V2 receptor Ki = 178.0 nM 6.75 Binding affinity at cloned human Vasopressin V2 receptor stably expressed in CHO... 12036368
Vasopressin V2 receptor Ki = 285.0 nM 6.54 Binding affinity at Vasopressin V2 receptor, performed using [3H]AVP on rat kidn... 12036368
Free fatty acid receptor 4 EC50 = 4775.24 nM 5.32 GPCR PRESTO-Tango dose-response in antagonist mode with target: FFAR4 -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724696 U2OS 24
- 10.6019/CHEMBL5724696 TERT-RPE1 24
- 10.6019/CHEMBL4689842 Fibroblast 10
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 8
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 8
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 8
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 8
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 8
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 8
- 10.6019/CHEMBL4689842 U2OS 8
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 8
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 8
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 8
- 10.6019/CHEMBL5209801 Apelin receptor 8
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 8
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 8
17850055 10.1021/jm061404q Vasopressin V1a receptor 5
12036368 10.1021/jm010544r Vasopressin V2 receptor 3
23075044 10.1021/jm301182j Homo sapiens 2

Data from ChEMBL 36 via Core Engine