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

ID: ALA113191

Chembl Id: CHEMBL113191

PubChem CID: 5329307

Max Phase: Preclinical

Molecular Formula: C18H25N3O3

Molecular Weight: 331.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H](N(C)CCc2ccccc2)C=C(C(=O)O)C[C@@H]1N

Standard InChI:  InChI=1S/C18H25N3O3/c1-12(22)20-17-15(19)10-14(18(23)24)11-16(17)21(2)9-8-13-6-4-3-5-7-13/h3-7,11,15-17H,8-10,19H2,1-2H3,(H,20,22)(H,23,24)/t15-,16+,17+/m0/s1

Standard InChI Key:  JGHGNWBFWJQGDZ-GVDBMIGSSA-N

Alternative Forms

1. Parent:

   

   ALA113191

   (3R,4R,5S)-5-amino-4-acetamido-3-[methyl(2-phenylethyl)amino]cyclohex-1-ene-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: 331.42

Molecular Weight (Monoisotopic): 331.1896

AlogP: 0.78

#Rotatable Bonds: 6

Polar Surface Area: 95.66

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.01

CX Basic pKa: 9.12

CX LogP: -1.67

CX LogD: -1.75

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: 0.32

References

1. Lew W, Wu H, Mendel DB, Escarpe PA, Chen X, Laver WG, Graves BJ, Kim CU..  (1998)  A new series of C3-aza carbocyclic influenza neuraminidase inhibitors: synthesis and inhibitory activity.,  8  (23): [PMID:9873727] [10.1016/s0960-894x(98)00587-3]

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