ID: ALA5182597

Max Phase: Preclinical

Molecular Formula: C22H21F3N4O9

Molecular Weight: 428.40

Representations

Canonical SMILES:  N=C(N)Nc1ccc(C(=O)Oc2cccc(CC(=O)N[C@@H](CC(=O)O)C(=O)O)c2)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C20H20N4O7.C2HF3O2/c21-20(22)23-13-6-4-12(5-7-13)19(30)31-14-3-1-2-11(8-14)9-16(25)24-15(18(28)29)10-17(26)27;3-2(4,5)1(6)7/h1-8,15H,9-10H2,(H,24,25)(H,26,27)(H,28,29)(H4,21,22,23);(H,6,7)/t15-;/m0./s1

Standard InChI Key:  POFPPQWVXGPJAA-RSAXXLAASA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 428.40

Molecular Weight (Monoisotopic): 428.1332

AlogP: 0.80

#Rotatable Bonds: 9

Polar Surface Area: 191.90

Molecular Species: ZWITTERION

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.29

CX Basic pKa: 8.54

CX LogP: -0.67

CX LogD: -3.17

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.14

Np Likeness Score: -0.41

References

1. Ikeda Z, Kakegawa K, Kikuchi F, Itono S, Oki H, Yashiro H, Hiyoshi H, Tsuchimori K, Hamagami K, Watanabe M, Sasaki M, Ishihara Y, Tohyama K, Kitazaki T, Maekawa T, Sasaki M..  (2022)  Design, Synthesis, and Biological Evaluation of a Novel Series of 4-Guanidinobenzoate Derivatives as Enteropeptidase Inhibitors with Low Systemic Exposure for the Treatment of Obesity.,  65  (12.0): [PMID:35686954] [10.1021/acs.jmedchem.2c00463]

Source

Source(1):

• Scientific Literature