(2S,4R)-Quinolin-3-ylmethyl 2-((((S)-3-Bromo-4,5-dihydroisoxazol-5-yl)methyl)carbamoyl)-4-(4-hydroxybenzamido)pyrrolidine-1-carboxylate

ID: ALA3357613

Chembl Id: CHEMBL3357613

PubChem CID: 118277764

Max Phase: Preclinical

Molecular Formula: C27H26BrN5O6

Molecular Weight: 596.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1C[C@@H](C(=O)NC[C@@H]2CC(Br)=NO2)N(C(=O)OCc2cnc3ccccc3c2)C1)c1ccc(O)cc1

Standard InChI:  InChI=1S/C27H26BrN5O6/c28-24-11-21(39-32-24)13-30-26(36)23-10-19(31-25(35)17-5-7-20(34)8-6-17)14-33(23)27(37)38-15-16-9-18-3-1-2-4-22(18)29-12-16/h1-9,12,19,21,23,34H,10-11,13-15H2,(H,30,36)(H,31,35)/t19-,21+,23+/m1/s1

Standard InChI Key:  QVOYKPGHRLCTID-NWSQWKLXSA-N

Alternative Forms

1. Parent:

   

   ALA3357613

   quinolin-3-ylmethyl (2S,4R)-2-[[(5S)-3-bromo-4,5-dihydro-1,2-oxazol-5-yl]methylcarbamoyl]-4-[(4-hydroxybenzoyl)amino]pyrrolidine-1-carboxylate

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: 596.44

Molecular Weight (Monoisotopic): 595.1066

AlogP: 3.06

#Rotatable Bonds: 7

Polar Surface Area: 142.45

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.47

CX Basic pKa: 4.07

CX LogP: 2.22

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.38

Np Likeness Score: -0.88

References

1. Klöck C, Herrera Z, Albertelli M, Khosla C..  (2014)  Discovery of potent and specific dihydroisoxazole inhibitors of human transglutaminase 2.,  57  (21): [PMID:25333388] [10.1021/jm501145a]

Source

Source(1):

• Scientific Literature