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

ID: ALA310004

Chembl Id: CHEMBL310004

PubChem CID: 493860

Max Phase: Preclinical

Molecular Formula: C19H34N2O4

Molecular Weight: 354.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H34N2O4/c1-4-6-7-8-9-10-15(5-2)25-17-12-14(19(23)24)11-16(20)18(17)21-13(3)22/h12,15-18H,4-11,20H2,1-3H3,(H,21,22)(H,23,24)/t15-,16-,17+,18+/m0/s1

Standard InChI Key:  XJOGOXCVUUHNTA-WNRNVDISSA-N

Alternative Forms

1. Parent:

   

   ALA310004

   (3R,4R,5S)-4-acetamido-5-amino-3-[(1S)-1-ethyloctoxy]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: 354.49

Molecular Weight (Monoisotopic): 354.2519

AlogP: 2.76

#Rotatable Bonds: 11

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: 4.11

CX Basic pKa: 9.34

CX LogP: 0.38

CX LogD: 0.38

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: 1.40

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