Isopropyl ((S)-(((2R,3R,4R,5R)-5-(3-(ethylamino)-2-oxopyrazin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4537291

PubChem CID: 155548084

Max Phase: Preclinical

Molecular Formula: C24H35N4O9P

Molecular Weight: 554.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCNc1nccn([C@@H]2O[C@H](CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)Oc3ccccc3)[C@@H](O)[C@@]2(C)O)c1=O

Standard InChI:  InChI=1S/C24H35N4O9P/c1-6-25-20-21(30)28(13-12-26-20)23-24(5,32)19(29)18(36-23)14-34-38(33,37-17-10-8-7-9-11-17)27-16(4)22(31)35-15(2)3/h7-13,15-16,18-19,23,29,32H,6,14H2,1-5H3,(H,25,26)(H,27,33)/t16-,18+,19+,23+,24+,38-/m0/s1

Standard InChI Key:  KMGIOIHZMGBBAJ-LKFYKZHASA-N

Molfile:  

 
     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA4537291

   ---

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: 554.54

Molecular Weight (Monoisotopic): 554.2142

AlogP: 1.82

#Rotatable Bonds: 12

Polar Surface Area: 170.47

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: 5.03

CX LogP: 0.71

CX LogD: 0.71

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: 0.19

References

1. Guo S, Xu M, Guo Q, Zhu F, Jiang X, Xie Y, Shen J..  (2019)  Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents.,  27  (5): [PMID:30683552] [10.1016/j.bmc.2019.01.007]

Source

Source(1):

• Scientific Literature