(S)-Methyl 2-((S)-2-((2S,3R)-3-Amino-S-(2-chlorophenoxy)-2-hydroxypentanamido)-4-methylpentanamido)-3-(4-hydroxyphenyl)propanoate

ID: ALA5197001

Chembl Id: CHEMBL5197001

PubChem CID: 168285580

Max Phase: Preclinical

Molecular Formula: C27H36ClN3O7

Molecular Weight: 550.05

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](O)[C@H](N)CCOc1cccc(Cl)c1

Standard InChI:  InChI=1S/C27H36ClN3O7/c1-16(2)13-22(25(34)31-23(27(36)37-3)14-17-7-9-19(32)10-8-17)30-26(35)24(33)21(29)11-12-38-20-6-4-5-18(28)15-20/h4-10,15-16,21-24,32-33H,11-14,29H2,1-3H3,(H,30,35)(H,31,34)/t21-,22+,23+,24+/m1/s1

Standard InChI Key:  YHYCZFIGZSESIE-SBFWRKJZSA-N

Alternative Forms

1. Parent:

   

   ALA5197001

   ---

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: 550.05

Molecular Weight (Monoisotopic): 549.2242

AlogP: 1.93

#Rotatable Bonds: 14

Polar Surface Area: 160.21

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.50

CX Basic pKa: 8.47

CX LogP: 2.19

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: -0.03

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