Ethyl (S)-2-((tert-butoxycarbonyl)amino)-4-((4-nitrobenzyl)carbamoyl)pent-4-enoate

ID: ALA5291468

Chembl Id: CHEMBL5291468

Max Phase: Preclinical

Molecular Formula: C20H27N3O7

Molecular Weight: 421.45

Names and Identifiers

Canonical SMILES:  C=C(C[C@H](NC(=O)OC(C)(C)C)C(=O)OCC)C(=O)NCc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H27N3O7/c1-6-29-18(25)16(22-19(26)30-20(3,4)5)11-13(2)17(24)21-12-14-7-9-15(10-8-14)23(27)28/h7-10,16H,2,6,11-12H2,1,3-5H3,(H,21,24)(H,22,26)/t16-/m0/s1

Standard InChI Key:  OQQCYQDTQXZLMW-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA5291468

   ---

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: 421.45

Molecular Weight (Monoisotopic): 421.1849

AlogP: 2.61

#Rotatable Bonds: 9

Polar Surface Area: 136.87

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.27

Np Likeness Score: -0.90

References

1. Khan MIH, Mahdi F, Penfornis P, Akins NS, Hossain MI, Kim SJ, Sulochana SP, Adam AT, Tran TD, Tan C, Paolo Claudio P, Paris JJ, Le HV..  (2023)  Synthesis and biological evaluation of tert-butyl ester and ethyl ester prodrugs of L-γ-methyleneglutamic acid amides for cancer.,  78  [PMID:36603398] [10.1016/j.bmc.2022.117137]

Source

Source(1):

• Scientific Literature