(3S,4S)-tert-butyl 3-(biphenylcarbonyloxy)-4-(5-fluoro-1H-benzo[d]imidazol-2-ylamino)pyrrolidine-1-carboxylate

ID: ALA3746637

Chembl Id: CHEMBL3746637

PubChem CID: 72946738

Max Phase: Preclinical

Molecular Formula: C29H29FN4O4

Molecular Weight: 516.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N1C[C@H](Nc2nc3cc(F)ccc3[nH]2)[C@@H](OC(=O)c2ccc(-c3ccccc3)cc2)C1

Standard InChI:  InChI=1S/C29H29FN4O4/c1-29(2,3)38-28(36)34-16-24(33-27-31-22-14-13-21(30)15-23(22)32-27)25(17-34)37-26(35)20-11-9-19(10-12-20)18-7-5-4-6-8-18/h4-15,24-25H,16-17H2,1-3H3,(H2,31,32,33)/t24-,25-/m0/s1

Standard InChI Key:  ONXOLONSBJTOEF-DQEYMECFSA-N

Alternative Forms

1. Parent:

   

   ALA3746637

   tert-butyl (3S,4S)-3-[(6-fluoro-1H-benzimidazol-2-yl)amino]-4-(4-phenylbenzoyl)oxypyrrolidine-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: 516.57

Molecular Weight (Monoisotopic): 516.2173

AlogP: 5.63

#Rotatable Bonds: 5

Polar Surface Area: 96.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.27

CX Basic pKa: 6.81

CX LogP: 5.88

CX LogD: 5.78

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: -0.72

References

1. De Tran Q, Bepary S, Lee GH, Cho H, Park WK, Lim HJ..  (2016)  Synthesis of (3S,4S)-4-aminopyrrolidine-3-ol derivatives and biological evaluation for their BACE1 inhibitory activities.,  26  (1): [PMID:26608551] [10.1016/j.bmcl.2015.11.033]

Source

Source(1):

• Scientific Literature