ID: ALA2420381

Max Phase: Preclinical

Molecular Formula: C24H33N5O4

Molecular Weight: 455.56

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)[C@H](CCCCN)NC(=O)c1ccc(N)c(NC(=O)[C@@H](N)CCc2ccccc2)c1

Standard InChI:  InChI=1S/C24H33N5O4/c1-33-24(32)20(9-5-6-14-25)28-22(30)17-11-13-18(26)21(15-17)29-23(31)19(27)12-10-16-7-3-2-4-8-16/h2-4,7-8,11,13,15,19-20H,5-6,9-10,12,14,25-27H2,1H3,(H,28,30)(H,29,31)/t19-,20-/m0/s1

Standard InChI Key:  PLKKJOBNGCNHOY-PMACEKPBSA-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: 455.56

Molecular Weight (Monoisotopic): 455.2533

AlogP: 1.57

#Rotatable Bonds: 12

Polar Surface Area: 162.56

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.87

CX Basic pKa: 10.21

CX LogP: 1.26

CX LogD: -2.26

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.18

Np Likeness Score: -0.24

References

1. Papakyriakou A, Zervoudi E, Theodorakis EA, Saveanu L, Stratikos E, Vourloumis D..  (2013)  Novel selective inhibitors of aminopeptidases that generate antigenic peptides.,  23  (17): [PMID:23916253] [10.1016/j.bmcl.2013.07.024]

2. Papakyriakou A, Zervoudi E, Tsoukalidou S, Mauvais FX, Sfyroera G, Mastellos DC, van Endert P, Theodorakis EA, Vourloumis D, Stratikos E..  (2015)  3,4-diaminobenzoic acid derivatives as inhibitors of the oxytocinase subfamily of M1 aminopeptidases with immune-regulating properties.,  58  (3): [PMID:25635706] [10.1021/jm501867s]

Source

Source(1):

• Scientific Literature