(S)-Methyl 2-(((2R,3S)-4-(((S)-1-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)-amino)-2-amino-3-hydroxy-4-oxobutyl)amino)-3-(4-hydroxyphenyl)propanoate

ID: ALA5209535

Chembl Id: CHEMBL5209535

PubChem CID: 168297105

Max Phase: Preclinical

Molecular Formula: C32H43N5O8

Molecular Weight: 625.72

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccc(O)cc1)NC[C@@H](N)[C@H](O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)OC

Standard InChI:  InChI=1S/C32H43N5O8/c1-18(2)13-25(29(40)37-27(32(43)45-4)15-20-16-34-24-8-6-5-7-22(20)24)36-30(41)28(39)23(33)17-35-26(31(42)44-3)14-19-9-11-21(38)12-10-19/h5-12,16,18,23,25-28,34-35,38-39H,13-15,17,33H2,1-4H3,(H,36,41)(H,37,40)/t23-,25+,26+,27+,28+/m1/s1

Standard InChI Key:  ZUBRZDDOAVYLJY-OFGRGEMESA-N

Alternative Forms

1. Parent:

   

   ALA5209535

   ---

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

Calculated Properties

Molecular Weight: 625.72

Molecular Weight (Monoisotopic): 625.3112

AlogP: 0.67

#Rotatable Bonds: 16

Polar Surface Area: 205.10

Molecular Species: NEUTRAL

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.50

CX Basic pKa: 7.96

CX LogP: 1.54

CX LogD: 1.02

Aromatic Rings: 3

Heavy Atoms: 45

QED Weighted: 0.11

Np Likeness Score: 0.26

References

1. Vourloumis D, Mavridis I, Athanasoulis A, Temponeras I, Koumantou D, Giastas P, Mpakali A, Magrioti V, Leib J, van Endert P, Stratikos E, Papakyriakou A..  (2022)  Discovery of Selective Nanomolar Inhibitors for Insulin-Regulated Aminopeptidase Based on α-Hydroxy-β-amino Acid Derivatives of Bestatin.,  65  (14.0): [PMID:35833347] [10.1021/acs.jmedchem.2c00904]

Source

Source(1):

• Scientific Literature