(3R,4R,5S)-4-Acetylamino-5-amino-3-benzyloxy-cyclohex-1-enecarboxylic acid

ID: ALA310217

Chembl Id: CHEMBL310217

PubChem CID: 493865

Max Phase: Preclinical

Molecular Formula: C16H20N2O4

Molecular Weight: 304.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H20N2O4/c1-10(19)18-15-13(17)7-12(16(20)21)8-14(15)22-9-11-5-3-2-4-6-11/h2-6,8,13-15H,7,9,17H2,1H3,(H,18,19)(H,20,21)/t13-,14+,15+/m0/s1

Standard InChI Key:  FBEKRJIKDMARPJ-RRFJBIMHSA-N

Alternative Forms

1. Parent:

   

   ALA310217

   (3R,4R,5S)-4-Acetylamino-5-amino-3-benzyloxy-cyclohex-1-enecarboxylic 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: 304.35

Molecular Weight (Monoisotopic): 304.1423

AlogP: 0.82

#Rotatable Bonds: 5

Polar Surface Area: 101.65

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: 9.33

CX LogP: -1.93

CX LogD: -1.93

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: 0.81

References

1. Kim CU, Lew W, Williams MA, Wu H, Zhang L, Chen X, Escarpe PA, Mendel DB, Laver WG, Stevens RC..  (1998)  Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors.,  41  (14): [PMID:9651151] [10.1021/jm980162u]

2. Wang Z, Cheng LP, Zhang XH, Pang W, Li L, Zhao JL..  (2017)  Design, synthesis and biological evaluation of novel oseltamivir derivatives as potent neuraminidase inhibitors.,  27  (24): [PMID:29141777] [10.1016/j.bmcl.2017.11.003]

Source

Source(1):

• Scientific Literature