(3R,4R,5S)-4-Acetamido-3-(pentan-3-yloxy)-5-((4-(thiophen-2-yl)benzyl)amino)cyclohex-1-enecarboxylic Acid

ID: ALA3342485

Chembl Id: CHEMBL3342485

PubChem CID: 85468898

Max Phase: Preclinical

Molecular Formula: C25H32N2O4S

Molecular Weight: 456.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](NCc2ccc(-c3cccs3)cc2)[C@H]1NC(C)=O

Standard InChI:  InChI=1S/C25H32N2O4S/c1-4-20(5-2)31-22-14-19(25(29)30)13-21(24(22)27-16(3)28)26-15-17-8-10-18(11-9-17)23-7-6-12-32-23/h6-12,14,20-22,24,26H,4-5,13,15H2,1-3H3,(H,27,28)(H,29,30)/t21-,22+,24+/m0/s1

Standard InChI Key:  YDCPBCKJEDRRRN-WMTXJRDZSA-N

Alternative Forms

1. Parent:

   

   ALA3342485

   (3R,4R,5S)-4-acetamido-3-pentan-3-yloxy-5-[(4-thiophen-2-ylphenyl)methylamino]cyclohexene-1-carboxylic acid

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: 456.61

Molecular Weight (Monoisotopic): 456.2083

AlogP: 4.37

#Rotatable Bonds: 10

Polar Surface Area: 87.66

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.18

CX Basic pKa: 8.75

CX LogP: 1.53

CX LogD: 1.52

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 0.02

References

1. Xie Y, Xu D, Huang B, Ma X, Qi W, Shi F, Liu X, Zhang Y, Xu W..  (2014)  Discovery of N-substituted oseltamivir derivatives as potent and selective inhibitors of H5N1 influenza neuraminidase.,  57  (20): [PMID:25255388] [10.1021/jm500892k]

2. Zhang J, Poongavanam V, Kang D, Bertagnin C, Lu H, Kong X, Ju H, Lu X, Gao P, Tian Y, Jia H, Desta S, Ding X, Sun L, Fang Z, Huang B, Liang X, Jia R, Ma X, Xu W, Murugan NA, Loregian A, Huang B, Zhan P, Liu X..  (2018)  Optimization of N-Substituted Oseltamivir Derivatives as Potent Inhibitors of Group-1 and -2 Influenza A Neuraminidases, Including a Drug-Resistant Variant.,  61  (14): [PMID:29965752] [10.1021/acs.jmedchem.8b00929]

3. Ju H, Hou L, Zhao F, Zhang Y, Jia R, Guizzo L, Bonomini A, Zhang J, Gao Z, Liang R, Bertagnin C, Kong X, Ma X, Kang D, Loregian A, Huang B, Liu X, Zhan P..  (2022)  Iterative Optimization and Structure-Activity Relationship Studies of Oseltamivir Amino Derivatives as Potent and Selective Neuraminidase Inhibitors via Targeting 150-Cavity.,  65  (17.0): [PMID:35939763] [10.1021/acs.jmedchem.1c01970]

Source

Source(1):

• Scientific Literature