ID: ALA2338312

Max Phase: Preclinical

Molecular Formula: C32H41N3O6

Molecular Weight: 563.70

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC[C@H](C)[C@@H]1C(=O)O[C@H]1C(=O)N[C@H]1C[C@H]1C[C@@H](CCc1ccccc1)NC(=O)[C@H](C)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C32H41N3O6/c1-4-20(2)27-28(41-31(27)38)30(37)35-26-18-24(26)17-25(16-15-22-11-7-5-8-12-22)34-29(36)21(3)33-32(39)40-19-23-13-9-6-10-14-23/h5-14,20-21,24-28H,4,15-19H2,1-3H3,(H,33,39)(H,34,36)(H,35,37)/t20-,21-,24+,25+,26-,27-,28+/m0/s1

Standard InChI Key:  YUZQDEBWPUFQAF-XZSSXHOESA-N

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

Properties

Molecular Weight: 563.70

Molecular Weight (Monoisotopic): 563.2995

AlogP: 3.90

#Rotatable Bonds: 14

Polar Surface Area: 122.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.54

CX Basic pKa:

CX LogP: 4.56

CX LogD: 4.56

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.30

Np Likeness Score: 0.25

References

1. Kawamura S, Unno Y, List A, Mizuno A, Tanaka M, Sasaki T, Arisawa M, Asai A, Groll M, Shuto S..  (2013)  Potent proteasome inhibitors derived from the unnatural cis-cyclopropane isomer of Belactosin A: synthesis, biological activity, and mode of action.,  56  (9): [PMID:23547757] [10.1021/jm4002296]

2. Kawamura S, Unno Y, Tanaka M, Sasaki T, Yamano A, Hirokawa T, Kameda T, Asai A, Arisawa M, Shuto S..  (2013)  Investigation of the noncovalent binding mode of covalent proteasome inhibitors around the transition state by combined use of cyclopropylic strain-based conformational restriction and computational modeling.,  56  (14): [PMID:23837692] [10.1021/jm400542h]

Source

Source(1):

• Scientific Literature