ID: ALA4227301

Max Phase: Preclinical

Molecular Formula: C26H32N6O5

Molecular Weight: 508.58

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=CC(=O)NCCCC[C@H](NC(=O)Cc1ccccc1)C(=O)N1CCN(c2cccc([N+](=O)[O-])n2)CC1

Standard InChI:  InChI=1S/C26H32N6O5/c1-2-24(33)27-14-7-6-11-21(28-25(34)19-20-9-4-3-5-10-20)26(35)31-17-15-30(16-18-31)22-12-8-13-23(29-22)32(36)37/h2-5,8-10,12-13,21H,1,6-7,11,14-19H2,(H,27,33)(H,28,34)/t21-/m0/s1

Standard InChI Key:  NIVSSMKVJURCCV-NRFANRHFSA-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: 508.58

Molecular Weight (Monoisotopic): 508.2434

AlogP: 1.84

#Rotatable Bonds: 12

Polar Surface Area: 137.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.35

CX Basic pKa:

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.19

Np Likeness Score: -1.14

References

1. Wodtke R, Hauser C, Ruiz-Gómez G, Jäckel E, Bauer D, Lohse M, Wong A, Pufe J, Ludwig FA, Fischer S, Hauser S, Greif D, Pisabarro MT, Pietzsch J, Pietsch M, Löser R..  (2018)  Nε-Acryloyllysine Piperazides as Irreversible Inhibitors of Transglutaminase 2: Synthesis, Structure-Activity Relationships, and Pharmacokinetic Profiling.,  61  (10): [PMID:29664627] [10.1021/acs.jmedchem.8b00286]

Source

Source(1):

• Scientific Literature