(3R,4R,5S)-4-Acetylamino-5-amino-3-((S)-1-ethyl-but-3-enyloxy)-cyclohex-1-enecarboxylic acid

ID: ALA311288

Chembl Id: CHEMBL311288

PubChem CID: 493859

Max Phase: Preclinical

Molecular Formula: C15H24N2O4

Molecular Weight: 296.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H24N2O4/c1-4-6-11(5-2)21-13-8-10(15(19)20)7-12(16)14(13)17-9(3)18/h4,8,11-14H,1,5-7,16H2,2-3H3,(H,17,18)(H,19,20)/t11-,12-,13+,14+/m0/s1

Standard InChI Key:  HQIVDWCSVLHHIC-IGQOVBAYSA-N

Alternative Forms

1. Parent:

   

   ALA311288

   (3R,4R,5S)-4-acetamido-5-amino-3-[(1S)-1-ethylbut-3-enoxy]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: 296.37

Molecular Weight (Monoisotopic): 296.1736

AlogP: 0.97

#Rotatable Bonds: 7

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: 4.19

CX Basic pKa: 9.34

CX LogP: -1.70

CX LogD: -1.70

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: 1.64

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