ID: ALA3416696

Max Phase: Preclinical

Molecular Formula: C23H31N7O5

Molecular Weight: 485.55

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccc(N)c(NC(=O)[C@@H](N)CCCNC(=N)N)c1

Standard InChI:  InChI=1S/C23H31N7O5/c1-35-22(34)19(11-13-4-7-15(31)8-5-13)30-20(32)14-6-9-16(24)18(12-14)29-21(33)17(25)3-2-10-28-23(26)27/h4-9,12,17,19,31H,2-3,10-11,24-25H2,1H3,(H,29,33)(H,30,32)(H4,26,27,28)/t17-,19-/m0/s1

Standard InChI Key:  JECKMXQKZJERLG-HKUYNNGSSA-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: 485.55

Molecular Weight (Monoisotopic): 485.2387

AlogP: 0.02

#Rotatable Bonds: 11

Polar Surface Area: 218.67

Molecular Species: BASE

HBA: 8

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.50

CX Basic pKa: 12.01

CX LogP: -0.67

CX LogD: -3.02

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.07

Np Likeness Score: -0.07

References

1. 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]

2. Mpakali A, Giastas P, Deprez-Poulain R, Papakyriakou A, Koumantou D, Gealageas R, Tsoukalidou S, Vourloumis D, Mavridis IM, Stratikos E, Saridakis E..  (2017)  Crystal Structures of ERAP2 Complexed with Inhibitors Reveal Pharmacophore Requirements for Optimizing Inhibitor Potency.,  8  (3): [PMID:28337326] [10.1021/acsmedchemlett.6b00505]

Source

Source(1):

• Scientific Literature