(S)-2-amino-N-((S)-1-((S)-1-(benzylamino)-3-((R)-3-hydroxy-2-oxoindolin-3-yl)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-3-(4-(benzyloxy)phenyl)propanamide

ID: ALA2337850

Chembl Id: CHEMBL2337850

PubChem CID: 71305068

Max Phase: Preclinical

Molecular Formula: C37H39N5O6

Molecular Weight: 649.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@@H](N)Cc1ccc(OCc2ccccc2)cc1)C(=O)N[C@@H](C[C@]1(O)C(=O)Nc2ccccc21)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C37H39N5O6/c1-24(40-34(44)30(38)20-25-16-18-28(19-17-25)48-23-27-12-6-3-7-13-27)33(43)41-32(35(45)39-22-26-10-4-2-5-11-26)21-37(47)29-14-8-9-15-31(29)42-36(37)46/h2-19,24,30,32,47H,20-23,38H2,1H3,(H,39,45)(H,40,44)(H,41,43)(H,42,46)/t24-,30-,32-,37+/m0/s1

Standard InChI Key:  PNAOQGBEWNBVLZ-NTFIELQZSA-N

Alternative Forms

1. Parent:

   

   ALA2337850

   (2S)-2-amino-N-[(2S)-1-[[(2S)-1-(benzylamino)-3-[(3R)-3-hydroxy-2-oxo-1H-indol-3-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]-3-(4-phenylmethoxyphenyl)propanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 649.75

Molecular Weight (Monoisotopic): 649.2900

AlogP: 2.67

#Rotatable Bonds: 14

Polar Surface Area: 171.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.45

CX Basic pKa: 7.73

CX LogP: 2.68

CX LogD: 2.18

Aromatic Rings: 4

Heavy Atoms: 48

QED Weighted: 0.12

Np Likeness Score: -0.06

References

1. Desvergne A, Genin E, Maréchal X, Gallastegui N, Dufau L, Richy N, Groll M, Vidal J, Reboud-Ravaux M..  (2013)  Dimerized linear mimics of a natural cyclopeptide (TMC-95A) are potent noncovalent inhibitors of the eukaryotic 20S proteasome.,  56  (8): [PMID:23540790] [10.1021/jm4002007]

2. Richy N, Sarraf D, Maréchal X, Janmamode N, Le Guével R, Genin E, Reboud-Ravaux M, Vidal J..  (2018)  Structure-based design of human immuno- and constitutive proteasomes inhibitors.,  145  [PMID:29339252] [10.1016/j.ejmech.2018.01.013]

Source

Source(1):

• Scientific Literature