(2R,3R,4S)-3-(2-azidoacetamido)-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate

ID: ALA1289862

Chembl Id: CHEMBL1289862

PubChem CID: 52948463

Max Phase: Preclinical

Molecular Formula: C11H16N4O8

Molecular Weight: 332.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=NCC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1O

Standard InChI:  InChI=1S/C11H16N4O8/c12-15-13-2-7(19)14-8-4(17)1-6(11(21)22)23-10(8)9(20)5(18)3-16/h1,4-5,8-10,16-18,20H,2-3H2,(H,14,19)(H,21,22)/t4-,5+,8+,9+,10+/m0/s1

Standard InChI Key:  OLOYDWMIOMMPCV-NCJYIMSCSA-N

Alternative Forms

1. Parent:

   

   ALA1289862

   (2R,3R,4S)-3-(2-azidoacetamido)-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylate

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: 332.27

Molecular Weight (Monoisotopic): 332.0968

AlogP: -2.78

#Rotatable Bonds: 7

Polar Surface Area: 205.31

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.10

CX Basic pKa:

CX LogP: -3.69

CX LogD: -7.26

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.16

Np Likeness Score: 1.28

References

1. Zou Y, Albohy A, Sandbhor M, Cairo CW..  (2010)  Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid.,  20  (24): [PMID:21036040] [10.1016/j.bmcl.2010.09.111]

2. Albohy A, Zhang Y, Smutova V, Pshezhetsky AV, Cairo CW..  (2013)  Identification of Selective Nanomolar Inhibitors of the Human Neuraminidase, NEU4.,  4  (6): [PMID:24900705] [10.1021/ml400080t]

3. Cairo CW.  (2014)  Inhibitors of the human neuraminidase enzymes,  5  (8): [10.1039/C4MD00089G]

4. Guo T, Héon-Roberts R, Zou C, Zheng R, Pshezhetsky AV, Cairo CW..  (2018)  Selective Inhibitors of Human Neuraminidase 1 (NEU1).,  61  (24): [PMID:30457869] [10.1021/acs.jmedchem.8b01411]

5. Bourguet E, Figurska S, Fra Czek MM..  (2022)  Human Neuraminidases: Structures and Stereoselective Inhibitors.,  65  (4.0): [PMID:35170942] [10.1021/acs.jmedchem.1c01612]

Source

Source(1):

• Scientific Literature