VIDARABINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC J05AB03 S01AD06
UNII 3XQD2MEW34
EPA CompTox DTXSID80873976

Structure

InChI Key OIRDTQYFTABQOQ-UHTZMRCNSA-N
Smiles Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
InChI
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H13N5O4
Molecular Weight 267.25
AlogP -1.98
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 139.54
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Human herpesvirus 1 DNA polymerase inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - 30000 -
Enzyme Lyase
- 82000 - - -
Enzyme Protease Serine protease Serine protease SC clan Serine protease S9B subfamily
- 62 - - -
Enzyme Transferase
- 50000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 103
Assay Description Organism Bioactivity Reference
Antiproliferative effects on CCRF-HSB-2 (human leukemia) cells. Homo sapiens 12.9 ug.mL-1
The cytotoxic activity in HL-60 cells Homo sapiens 20.9 ug.mL-1
In vitro cytotoxicity against herpes simplex virus type-1 (HSV-1) HF strain in infected KB cells Human herpesvirus 1 39.0 ug.mL-1
Inhibitory activity against herpes simplex virus type-1 (HSV-1) replication in KB cells Human herpesvirus 1 5.6 ug.mL-1
Antiretroviral activity in the XC-plaque assay using Moloney leukemia virus (MoLV) as a model for human immunodeficiency virus (HIV). Moloney murine leukemia virus 1.0 ug.mL-1
Compound was evaluated for antiviral activity in rabbit kidney cells infected with vaccinia virus Oryctolagus cuniculus 0.4 ug.mL-1
Concentration required to inhibit incorporation of [1,'2'-3H]dUrd into DNA of primary rabbit kidney (PRK) cells by 50% Oryctolagus cuniculus 10.0 ug.mL-1
Concentration required to inhibit incorporation of [Me-3H]-dThd into DNA of primary rabbit kidney (PRK) cells by 50% Oryctolagus cuniculus 20.0 ug.mL-1
Concentration required to reduce HSV-1 induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells; 4-10 Oryctolagus cuniculus 7.0 ug.mL-1
Concentration required to reduce HSV-1(KOS) induced cytopathogenicity by 50% was measured Oryctolagus cuniculus 4.0 ug.mL-1
Concentration required to reduce HSV-1(KOS) induced cytopathogenicity by 50% was measured by the addition of [1,'2'-3H]dUrd Oryctolagus cuniculus 1.0 ug.mL-1
Concentration required to reduce HSV-1(KOS) induced cytopathogenicity by 50% was measured by the addition of [Me-3H]-dThd Oryctolagus cuniculus 1.0 ug.mL-1
Concentration required to reduce HSV-2 induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells; 2-4 Oryctolagus cuniculus 3.0 ug.mL-1
Concentration required to reduce TK-HSV-1 (B2006) induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells Oryctolagus cuniculus 10.0 ug.mL-1
Stability in human recombinant CD26 assessed as inhibition of 6-aminoquinoline formation in presence of vildagliptin None 50.0 %
Inhibition of human DPP4 from human Caco-2 cells Homo sapiens 62.0 nM
Inhibition of hepcidin mRNA expression in human Hep3B cells at 250 uM after 30 mins by qRT-PCR analysis Homo sapiens 40.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 103.09 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 90.86 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 17.44 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 6.8 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 13.1 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 12.75 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 33.05 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.29 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.72 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -15.34 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.763 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.01 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.01 %

Related Entries

Cross References

Resources Reference
ChEBI 45327
ChEMBL CHEMBL1090
DrugBank DB00194
DrugCentral 2818
FDA SRS 3XQD2MEW34
Human Metabolome Database HMDB0014340
Guide to Pharmacology 4806
KEGG D06298
PDB RAB
PubChem 32326
SureChEMBL SCHEMBL110914
ZINC ZINC000000970363
CONTENTS