5-[(S)-3-(3-Chloro-5-fluoro-benzylcarbamoyl)-3-hydroxy-2-oxopyrrolidin-1-yl]-1H-indole-2-carboxylic Acid Ethylamide

ID: ALA4445117

Chembl Id: CHEMBL4445117

PubChem CID: 89855793

Max Phase: Preclinical

Molecular Formula: C23H22ClFN4O4

Molecular Weight: 472.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCNC(=O)c1cc2cc(N3CC[C@](O)(C(=O)NCc4cc(F)cc(Cl)c4)C3=O)ccc2[nH]1

Standard InChI:  InChI=1S/C23H22ClFN4O4/c1-2-26-20(30)19-10-14-9-17(3-4-18(14)28-19)29-6-5-23(33,22(29)32)21(31)27-12-13-7-15(24)11-16(25)8-13/h3-4,7-11,28,33H,2,5-6,12H2,1H3,(H,26,30)(H,27,31)/t23-/m0/s1

Standard InChI Key:  TUPCUCNBNOUJJC-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA4445117

   5-[(3S)-3-[(3-chloro-5-fluorophenyl)methylcarbamoyl]-3-hydroxy-2-oxopyrrolidin-1-yl]-N-ethyl-1H-indole-2-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.90

Molecular Weight (Monoisotopic): 472.1314

AlogP: 2.49

#Rotatable Bonds: 6

Polar Surface Area: 114.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.76

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -1.28

References

1. Heinrich T, Seenisamy J, Becker F, Blume B, Bomke J, Dietz M, Eckert U, Friese-Hamim M, Gunera J, Hansen K, Leuthner B, Musil D, Pfalzgraf J, Rohdich F, Siegl C, Spuck D, Wegener A, Zenke FT..  (2019)  Identification of Methionine Aminopeptidase-2 (MetAP-2) Inhibitor M8891: A Clinical Compound for the Treatment of Cancer.,  62  (24): [PMID:31725285] [10.1021/acs.jmedchem.9b01070]

Source

Source(1):

• Scientific Literature