(S)-Methyl 2-(4-Amino-3-((S)-2-amino-5-guanidinopentanamido)benzamido)-3-(4-hydroxyphenyl)-propanoate

ID: ALA3416696

Chembl Id: CHEMBL3416696

PubChem CID: 118734263

Max Phase: Preclinical

Molecular Formula: C23H31N7O5

Molecular Weight: 485.55

Molecule Type: Small molecule

Names and Identifiers

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

Alternative Forms

1. Parent:

   

   ALA3416696

   ---

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

Calculated 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