(3R,4R,5S)-4-Acetylamino-5-amino-3-(3-biphenyl-4-yl-propoxy)-cyclohex-1-enecarboxylic acid

ID: ALA81083

Chembl Id: CHEMBL81083

PubChem CID: 493870

Max Phase: Preclinical

Molecular Formula: C24H28N2O4

Molecular Weight: 408.50

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]1OCCCc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C24H28N2O4/c1-16(27)26-23-21(25)14-20(24(28)29)15-22(23)30-13-5-6-17-9-11-19(12-10-17)18-7-3-2-4-8-18/h2-4,7-12,15,21-23H,5-6,13-14,25H2,1H3,(H,26,27)(H,28,29)/t21-,22+,23+/m0/s1

Standard InChI Key:  WLWJACADVNSTQF-YTFSRNRJSA-N

Alternative Forms

1. Parent:

   

   ALA81083

   (3R,4R,5S)-4-acetamido-5-amino-3-[3-(4-phenylphenyl)propoxy]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: 408.50

Molecular Weight (Monoisotopic): 408.2049

AlogP: 2.92

#Rotatable Bonds: 8

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: 3.94

CX Basic pKa: 9.34

CX LogP: 0.45

CX LogD: 0.45

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: 0.56

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. Murumkar PR, Le L, Truong TN, Yadav MR.  (2011)  Determination of structural requirements of influenza neuraminidase type A inhibitors and binding interaction analysis with the active site of A/H1N1 by 3D-QSAR CoMFA and CoMSIA modeling,  2  (8): [10.1039/C1MD00050K]

3. 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