(S)-Methyl 2-(((3R,4S)-5-(((S)-1-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)-amino)-3-amino-4-hydroxy-5-oxopentyl)amino)-3-(4-hydroxyphenyl)propanoate

ID: ALA5171198

Chembl Id: CHEMBL5171198

PubChem CID: 168269001

Max Phase: Preclinical

Molecular Formula: C33H45N5O8

Molecular Weight: 639.75

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccc(O)cc1)NCC[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/C33H45N5O8/c1-19(2)15-26(30(41)38-28(33(44)46-4)17-21-18-36-25-8-6-5-7-23(21)25)37-31(42)29(40)24(34)13-14-35-27(32(43)45-3)16-20-9-11-22(39)12-10-20/h5-12,18-19,24,26-29,35-36,39-40H,13-17,34H2,1-4H3,(H,37,42)(H,38,41)/t24-,26+,27+,28+,29+/m1/s1

Standard InChI Key:  COMBCDCRFAXRAT-QDXQZTBOSA-N

Alternative Forms

1. Parent:

   

   ALA5171198

   ---

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: 639.75

Molecular Weight (Monoisotopic): 639.3268

AlogP: 1.06

#Rotatable Bonds: 17

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: 8.40

CX LogP: 1.54

CX LogD: 0.68

Aromatic Rings: 3

Heavy Atoms: 46

QED Weighted: 0.10

Np Likeness Score: 0.30

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