Methyl 2-((S)-2-((2S,3R)-3-Amino-2-hydroxy-4-(3,4,5-trifluorophenoxy)butanamido)-4-methylpentanamido)-3-(1H-indol-3-yl)propanoate

ID: ALA5195885

Chembl Id: CHEMBL5195885

PubChem CID: 168292493

Max Phase: Preclinical

Molecular Formula: C28H33F3N4O6

Molecular Weight: 578.59

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](O)[C@H](N)COc1cc(F)c(F)c(F)c1

Standard InChI:  InChI=1S/C28H33F3N4O6/c1-14(2)8-22(34-27(38)25(36)20(32)13-41-16-10-18(29)24(31)19(30)11-16)26(37)35-23(28(39)40-3)9-15-12-33-21-7-5-4-6-17(15)21/h4-7,10-12,14,20,22-23,25,33,36H,8-9,13,32H2,1-3H3,(H,34,38)(H,35,37)/t20-,22+,23+,25+/m1/s1

Standard InChI Key:  ZGOYLLCQBCBXHF-GIQJJWITSA-N

Alternative Forms

1. Parent:

   

   ALA5195885

   ---

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: 578.59

Molecular Weight (Monoisotopic): 578.2352

AlogP: 2.08

#Rotatable Bonds: 13

Polar Surface Area: 155.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.47

CX Basic pKa: 7.91

CX LogP: 2.59

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.15

Np Likeness Score: -0.18

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