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((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,4-difluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methyltriphosphoric acid

ID: ALA4440367

PubChem CID: 76286401

Max Phase: Preclinical

Molecular Formula: C10H15F2N2O14P3

Molecular Weight: 518.15

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  C[C@]1(F)[C@H](n2ccc(=O)[nH]c2=O)O[C@](F)(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@H]1O

Standard InChI:  InChI=1S/C10H15F2N2O14P3/c1-9(11)6(16)10(12,26-7(9)14-3-2-5(15)13-8(14)17)4-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-3,6-7,16H,4H2,1H3,(H,21,22)(H,23,24)(H,13,15,17)(H2,18,19,20)/t6-,7+,9+,10+/m0/s1

Standard InChI Key:  MTLKGBSETBFUQX-MVHNUAHISA-N

Molfile:  

 
     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   14.0161  -17.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4288  -17.1899    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6112  -17.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4317  -16.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8444  -17.1940    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.2528  -16.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8473  -16.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2601  -17.2023    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685  -16.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6675  -18.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9622  -18.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5495  -19.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7323  -19.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1409  -20.3327    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.9192  -19.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9907  -18.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3278  -18.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7035  -18.4469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4030  -18.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1130  -18.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1262  -17.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4232  -17.2302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7070  -17.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0034  -17.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8399  -17.2506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5024  -20.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9669  -17.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5515  -17.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1361  -17.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4247  -16.3727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9576  -19.2494    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  2  0
  8  7  2  0
  9  8  1  0
 15 13  1  0
 13 16  1  0
 16 17  1  0
 17 10  1  0
 10 15  1  0
 16 18  1  1
 18 19  1  0
 18 23  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 21 25  2  0
 13 12  1  1
 13 14  1  0
 15 26  1  6
 10 11  1  1
 11 27  1  0
 27  8  1  0
  8 28  1  0
 28  5  1  0
  5 29  1  0
 29  2  1  0
  2 30  2  0
 10 31  1  0
M  END

Associated Targets(Human)

POLA1 Tclin DNA polymerase alpha subunit (225 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLB Tchem DNA polymerase beta (23632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLG Tchem DNA polymerase gamma subunit 1 (50 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

NS5B Hepatitis C virus NS5B RNA-dependent RNA polymerase (3026 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Calculated Properties

Molecular Weight: 518.15Molecular Weight (Monoisotopic): 517.9704AlogP: -0.84#Rotatable Bonds: 8
Polar Surface Area: 244.14Molecular Species: ACIDHBA: 11HBD: 6
#RO5 Violations: 3HBA (Lipinski): 16HBD (Lipinski): 6#RO5 Violations (Lipinski): 3
CX Acidic pKa: 0.89CX Basic pKa: CX LogP: -1.64CX LogD: -9.05
Aromatic Rings: 1Heavy Atoms: 31QED Weighted: 0.23Np Likeness Score: 0.86

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