tert-butyl(S)-1-((S)-1-((S)-1-(benzylamino)-3-((R)-3-hydroxy-2-oxoindolin-3-yl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-3-(4-(benzyloxy)phenyl)-1-oxopropan-2-ylcarbamate

ID: ALA2337849

Chembl Id: CHEMBL2337849

PubChem CID: 49859747

Max Phase: Preclinical

Molecular Formula: C42H47N5O8

Molecular Weight: 749.87

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C42H47N5O8/c1-27(36(48)45-35(37(49)43-25-29-13-7-5-8-14-29)24-42(53)32-17-11-12-18-33(32)46-39(42)51)44-38(50)34(47-40(52)55-41(2,3)4)23-28-19-21-31(22-20-28)54-26-30-15-9-6-10-16-30/h5-22,27,34-35,53H,23-26H2,1-4H3,(H,43,49)(H,44,50)(H,45,48)(H,46,51)(H,47,52)/t27-,34-,35-,42+/m0/s1

Standard InChI Key:  LEFDHTPNDGQXKD-KUNNGYQLSA-N

Alternative Forms

1. Parent:

   

   ALA2337849

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

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: 749.87

Molecular Weight (Monoisotopic): 749.3425

AlogP: 4.24

#Rotatable Bonds: 15

Polar Surface Area: 184.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.40

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.17

Aromatic Rings: 4

Heavy Atoms: 55

QED Weighted: 0.10

Np Likeness Score: -0.24

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. Desvergne A, Cheng Y, Grosay-Gaudrel S, Maréchal X, Reboud-Ravaux M, Genin E, Vidal J..  (2014)  Noncovalent fluorescent probes of human immuno- and constitutive proteasomes.,  57  (21): [PMID:25333324] [10.1021/jm5011429]

3. 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