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

ID: ALA5191661

Chembl Id: CHEMBL5191661

PubChem CID: 164513565

Max Phase: Preclinical

Molecular Formula: C28H36N4O7

Molecular Weight: 540.62

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)COc1ccc(O)cc1

Standard InChI:  InChI=1S/C28H36N4O7/c1-16(2)12-23(31-27(36)25(34)21(29)15-39-19-10-8-18(33)9-11-19)26(35)32-24(28(37)38-3)13-17-14-30-22-7-5-4-6-20(17)22/h4-11,14,16,21,23-25,30,33-34H,12-13,15,29H2,1-3H3,(H,31,36)(H,32,35)/t21-,23+,24+,25+/m1/s1

Standard InChI Key:  WXYVFLSKRTUFAE-VZVHPENPSA-N

Alternative Forms

1. Parent:

   

   ALA5191661

   ---

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: 540.62

Molecular Weight (Monoisotopic): 540.2584

AlogP: 1.37

#Rotatable Bonds: 13

Polar Surface Area: 176.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.92

CX Basic pKa: 7.90

CX LogP: 1.86

CX LogD: 1.23

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.18

Np Likeness Score: 0.17

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