(2S)-isopropyl 2-((4-chlorophenoxy)(((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-fluoro-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)phosphorylamino)propanoate

ID: ALA4476774

PubChem CID: 90247955

Max Phase: Preclinical

Molecular Formula: C22H28ClFN3O10P

Molecular Weight: 579.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](C)NP(=O)(OC[C@@]1(F)O[C@@H](n2ccc(=O)[nH]c2=O)[C@](C)(O)[C@@H]1O)Oc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C22H28ClFN3O10P/c1-12(2)35-17(29)13(3)26-38(33,37-15-7-5-14(23)6-8-15)34-11-22(24)18(30)21(4,32)19(36-22)27-10-9-16(28)25-20(27)31/h5-10,12-13,18-19,30,32H,11H2,1-4H3,(H,26,33)(H,25,28,31)/t13-,18-,19+,21+,22+,38?/m0/s1

Standard InChI Key:  ZIKSMXHRIKVGDU-MPRLAMPNSA-N

Molfile:  

 
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   23.8799  -26.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   26.7073  -27.6937    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   22.3314  -24.9477    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4476774

   propan-2-yl (2S)-2-[[(4-chlorophenoxy)-[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-2-fluoro-3,4-dihydroxy-4-methyloxolan-2-yl]methoxy]phosphoryl]amino]propanoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 579.90

Molecular Weight (Monoisotopic): 579.1185

AlogP: 1.63

#Rotatable Bonds: 10

Polar Surface Area: 178.41

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: 1.57

CX LogD: 1.57

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: 0.12

References

1. Wang G, Dyatkina N, Prhavc M, Williams C, Serebryany V, Hu Y, Huang Y, Wan J, Wu X, Deval J, Fung A, Jin Z, Tan H, Shaw K, Kang H, Zhang Q, Tam Y, Stoycheva A, Jekle A, Smith DB, Beigelman L..  (2019)  Synthesis and Anti-HCV Activities of 4'-Fluoro-2'-Substituted Uridine Triphosphates and Nucleotide Prodrugs: Discovery of 4'-Fluoro-2'- C-methyluridine 5'-Phosphoramidate Prodrug (AL-335) for the Treatment of Hepatitis C Infection.,  62  (9): [PMID:30951311] [10.1021/acs.jmedchem.9b00143]

Source

Source(1):

• Scientific Literature