Trisodium(R)-((((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryloxy)(3-phenoxyphenyl)methylphosphonate

ID: ALA4102509

Chembl Id: CHEMBL4102509

PubChem CID: 137656408

Max Phase: Preclinical

Molecular Formula: C22H22N3Na3O12P2

Molecular Weight: 585.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@@H]2O[C@H](COP(=O)([O-])O[C@@H](c3cccc(Oc4ccccc4)c3)P(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)n1.[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C22H25N3O12P2.3Na/c23-17-9-10-25(22(28)24-17)20-19(27)18(26)16(36-20)12-34-39(32,33)37-21(38(29,30)31)13-5-4-8-15(11-13)35-14-6-2-1-3-7-14;;;/h1-11,16,18-21,26-27H,12H2,(H,32,33)(H2,23,24,28)(H2,29,30,31);;;/q;3*+1/p-3/t16-,18-,19-,20-,21-;;;/m1.../s1

Standard InChI Key:  SHDOSRBONQBOED-GYKYLPKRSA-K

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: 585.40

Molecular Weight (Monoisotopic): 585.0913

AlogP: 1.25

#Rotatable Bonds: 10

Polar Surface Area: 233.12

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.08

CX Basic pKa: ┄

CX LogP: 0.24

CX LogD: -4.51

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.18

Np Likeness Score: 0.61

References

1. Guo J, Li W, Xue W, Ye XS..  (2017)  Transition State-Based Sialyltransferase Inhibitors: Mimicking Oxocarbenium Ion by Simple Amide.,  60  (5): [PMID:28165727] [10.1021/acs.jmedchem.6b01644]

2. Montgomery AP,Dobie C,Szabo R,Hallam L,Ranson M,Yu H,Skropeta D.  (2020)  Design, synthesis and evaluation of carbamate-linked uridyl-based inhibitors of human ST6Gal I.,  28  (14): [PMID:32616185] [10.1016/j.bmc.2020.115561]

Source

Source(1):

• Scientific Literature