5-Acetamido-9-(4-carboxyphenyl)-2,6-anhydro-4-guanidino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid

ID: ALA4064112

Chembl Id: CHEMBL4064112

PubChem CID: 137635553

Max Phase: Preclinical

Molecular Formula: C21H25N7O8

Molecular Weight: 503.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)Cn2cc(-c3ccc(C(=O)O)cc3)nn2)OC(C(=O)O)=C[C@@H]1NC(=N)N

Standard InChI:  InChI=1S/C21H25N7O8/c1-9(29)24-16-12(25-21(22)23)6-15(20(34)35)36-18(16)17(31)14(30)8-28-7-13(26-27-28)10-2-4-11(5-3-10)19(32)33/h2-7,12,14,16-18,30-31H,8H2,1H3,(H,24,29)(H,32,33)(H,34,35)(H4,22,23,25)/t12-,14+,16+,17+,18+/m0/s1

Standard InChI Key:  ZRSHDFLAAXMUPG-SEYFSXTGSA-N

Alternative Forms

1. Parent:

   

   ALA4064112

   ---

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: 503.47

Molecular Weight (Monoisotopic): 503.1765

AlogP: -1.91

#Rotatable Bonds: 9

Polar Surface Area: 246.00

Molecular Species: ZWITTERION

HBA: 10

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.27

CX Basic pKa: 11.52

CX LogP: -3.78

CX LogD: -6.76

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.14

Np Likeness Score: 0.02

References

1. Guo T, Dätwyler P, Demina E, Richards MR, Ge P, Zou C, Zheng R, Fougerat A, Pshezhetsky AV, Ernst B, Cairo CW..  (2018)  Selective Inhibitors of Human Neuraminidase 3.,  61  (5): [PMID:29425031] [10.1021/acs.jmedchem.7b01574]

2.  (2018)  Methods of preventing or treating atherosclerosis with inhibitors of specific isoenzymes of human neuraminidase, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data