ID: ALA2086892

Max Phase: Preclinical

Molecular Formula: C23H29N3O4S2

Molecular Weight: 475.64

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCCOC(=O)NS(=O)(=O)c1sc(CC(C)C)cc1-c1cccc(Cn2ccnc2)c1

Standard InChI:  InChI=1S/C23H29N3O4S2/c1-4-5-11-30-23(27)25-32(28,29)22-21(14-20(31-22)12-17(2)3)19-8-6-7-18(13-19)15-26-10-9-24-16-26/h6-10,13-14,16-17H,4-5,11-12,15H2,1-3H3,(H,25,27)

Standard InChI Key:  ZWDDUNMMFDVANI-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 475.64

Molecular Weight (Monoisotopic): 475.1599

AlogP: 5.07

#Rotatable Bonds: 10

Polar Surface Area: 90.29

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.61

CX Basic pKa: 6.47

CX LogP: 4.58

CX LogD: 4.78

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: -0.98

References

1. Murugaiah AM, Wu X, Wallinder C, Mahalingam AK, Wan Y, Sköld C, Botros M, Guimond MO, Joshi A, Nyberg F, Gallo-Payet N, Hallberg A, Alterman M..  (2012)  From the first selective non-peptide AT(2) receptor agonist to structurally related antagonists.,  55  (5): [PMID:22248302] [10.1021/jm2015099]

2. Guimond MO, Hallberg M, Gallo-Payet N, Wallinder C..  (2014)  Saralasin and Sarile Are AT2 Receptor Agonists.,  5  (10): [PMID:25313325] [10.1021/ml500278g]

3. Wallinder C, Sköld C, Botros M, Guimond MO, Hallberg M, Gallo-Payet N, Karlén A, Alterman M..  (2015)  Interconversion of Functional Activity by Minor Structural Alterations in Nonpeptide AT2 Receptor Ligands.,  6  (2): [PMID:25699147] [10.1021/ml500427r]

4. Sallander J, Wallinder C, Hallberg A, Åqvist J, Gutiérrez-de-Terán H..  (2016)  Structural determinants of subtype selectivity and functional activity of angiotensin II receptors.,  26  (4): [PMID:26810314] [10.1016/j.bmcl.2015.10.084]

5. Wannberg J, Isaksson R, Bremberg U, Backlund M, Sävmarker J, Hallberg M, Larhed M..  (2018)  A convenient transesterification method for synthesis of AT2 receptor ligands with improved stability in human liver microsomes.,  28  (3): [PMID:29279275] [10.1016/j.bmcl.2017.11.042]

6. Wannberg J,Gising J,Lindman J,Salander J,Gutiérrez-de-Terán H,Ablahad H,Hamid S,Grönbladh A,Spizzo I,Gaspari TA,Widdop RE,Hallberg A,Backlund M,Leśniak A,Hallberg M,Larhed M.  (2021)  N-(Methyloxycarbonyl)thiophene sulfonamides as high affinity AT2 receptor ligands.,  29  [PMID:33309749] [10.1016/j.bmc.2020.115859]

7. Gopalan G, Palo-Nieto C, Petersen NN, Hallberg M, Larhed M..  (2022)  Angiotensin II AT2 receptor ligands with phenylthiazole scaffolds.,  65  [PMID:35550979] [10.1016/j.bmc.2022.116790]

Source

Source(1):

• Scientific Literature