(2R,3R,4S)-3-acetamido-4-(3-(2-(naphthalen-1-ylthio)acetyl)guanidino)-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

ID: ALA3355596

Chembl Id: CHEMBL3355596

PubChem CID: 118720939

Max Phase: Preclinical

Molecular Formula: C24H28N4O8S

Molecular Weight: 532.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1NC(=N)NC(=O)CSc1cccc2ccccc12

Standard InChI:  InChI=1S/C24H28N4O8S/c1-12(30)26-20-15(9-17(23(34)35)36-22(20)21(33)16(31)10-29)27-24(25)28-19(32)11-37-18-8-4-6-13-5-2-3-7-14(13)18/h2-9,15-16,20-22,29,31,33H,10-11H2,1H3,(H,26,30)(H,34,35)(H3,25,27,28,32)/t15-,16+,20+,21+,22+/m0/s1

Standard InChI Key:  UVRXMGICDWZBSS-NTZWLTRZSA-N

Alternative Forms

1. Parent:

   

   ALA3355596

   ---

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: 532.58

Molecular Weight (Monoisotopic): 532.1628

AlogP: -0.47

#Rotatable Bonds: 9

Polar Surface Area: 201.30

Molecular Species: ZWITTERION

HBA: 9

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.25

CX Basic pKa: 8.76

CX LogP: -2.86

CX LogD: -2.88

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.12

Np Likeness Score: 0.18

References

1. Xie Y, Xu D, Huang B, Ma X, Qi W, Shi F, Liu X, Zhang Y, Xu W..  (2014)  Discovery of N-substituted oseltamivir derivatives as potent and selective inhibitors of H5N1 influenza neuraminidase.,  57  (20): [PMID:25255388] [10.1021/jm500892k]

2. Wang K, Lei Z, Zhao L, Chen B, Yang F, Liu K, Zhu H, Zhao H, Cao R, Zhang K, Tian Y..  (2020)  Design, synthesis and biological evaluation of oseltamivir derivatives containing pyridyl group as potent inhibitors of neuraminidase for influenza A.,  185  [PMID:31708183] [10.1016/j.ejmech.2019.111841]

Source

Source(1):

• Scientific Literature