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

ID: ALA298659

Chembl Id: CHEMBL298659

PubChem CID: 493864

Max Phase: Preclinical

Molecular Formula: C15H18N2O4

Molecular Weight: 290.32

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]1Oc1ccccc1

Standard InChI:  InChI=1S/C15H18N2O4/c1-9(18)17-14-12(16)7-10(15(19)20)8-13(14)21-11-5-3-2-4-6-11/h2-6,8,12-14H,7,16H2,1H3,(H,17,18)(H,19,20)/t12-,13+,14+/m0/s1

Standard InChI Key:  DKWGERBFVMJXSN-BFHYXJOUSA-N

Alternative Forms

1. Parent:

   

   ALA298659

   (3R,4R,5S)-4-Acetylamino-5-amino-3-phenoxy-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: 290.32

Molecular Weight (Monoisotopic): 290.1267

AlogP: 0.68

#Rotatable Bonds: 4

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: 3.85

CX Basic pKa: 9.13

CX LogP: -1.97

CX LogD: -1.97

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.76

Np Likeness Score: 0.89

References

1. Williams MA, Lew W, Mendel DB, Tai CY, Escarpe PA, Laver W, Stevens RC, Kim CU.  (1997)  Structure-activity relationships of carbocyclic influenza neuraminidase inhibitors,  7  (14): [10.1016/S0960-894X(97)00333-8]

2. 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]

3. 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]

4. 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