(2S)-isopropyl 2-((((4R,5R,7R,8R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-8-hydroxy-1,6-dioxaspiro[3.4]octan-7-yl)methoxy)(phenoxy)phosphorylamino)propanoate

ID: ALA3122101

Chembl Id: CHEMBL3122101

PubChem CID: 66694043

Max Phase: Preclinical

Molecular Formula: C23H30N3O10P

Molecular Weight: 539.48

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](C)NP(=O)(OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@@]2(CCO2)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C23H30N3O10P/c1-14(2)34-20(29)15(3)25-37(31,36-16-7-5-4-6-8-16)33-13-17-19(28)23(10-12-32-23)21(35-17)26-11-9-18(27)24-22(26)30/h4-9,11,14-15,17,19,21,28H,10,12-13H2,1-3H3,(H,25,31)(H,24,27,30)/t15-,17+,19+,21+,23+,37?/m0/s1

Standard InChI Key:  WOXTVQSWMMHKGA-YNMIPJKBSA-N

Associated Targets(Human)

Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Hepatitis C virus (23859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chikungunya virus (1339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sindbis virus (1599 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dengue virus type 2 (2400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 539.48Molecular Weight (Monoisotopic): 539.1669AlogP: 1.09#Rotatable Bonds: 10
Polar Surface Area: 167.41Molecular Species: NEUTRALHBA: 11HBD: 3
#RO5 Violations: 2HBA (Lipinski): 13HBD (Lipinski): 3#RO5 Violations (Lipinski): 2
CX Acidic pKa: 9.59CX Basic pKa: CX LogP: 0.57CX LogD: 0.56
Aromatic Rings: 2Heavy Atoms: 37QED Weighted: 0.29Np Likeness Score: 0.47

References

1. Jonckers TH, Vandyck K, Vandekerckhove L, Hu L, Tahri A, Van Hoof S, Lin TI, Vijgen L, Berke JM, Lachau-Durand S, Stoops B, Leclercq L, Fanning G, Samuelsson B, Nilsson M, Rosenquist Å, Simmen K, Raboisson P..  (2014)  Nucleotide prodrugs of 2'-deoxy-2'-spirooxetane ribonucleosides as novel inhibitors of the HCV NS5B polymerase.,  57  (5): [PMID:24345201] [10.1021/jm4015422]
2. Grosse S, Tahri A, Raboisson P, Houpis Y, Stoops B, Jacoby E, Neefs JM, Van Loock M, Goethals O, Geluykens P, Bonfanti JF, Jonckers THM..  (2022)  From Oxetane to Thietane: Extending the Antiviral Spectrum of 2'-Spirocyclic Uridines by Substituting Oxygen with Sulfur.,  13  (12.0): [PMID:36518706] [10.1021/acsmedchemlett.2c00372]

Source