Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-15 22:03:03 UTC
HMDB IDHMDB0014340
Secondary Accession Numbers
  • HMDB14340
Metabolite Identification
Common NameVidarabine
DescriptionVidarabine, also known as ara a or spongoadenosine, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Vidarabine is a drug which is used for treatment of chickenpox - varicella, herpes zoster and herpes simplex. Vidarabine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Vidarabine.
Structure
Data?1676498583
Synonyms
ValueSource
2-(6-AMINO-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diolChEBI
9-beta-D-Arabinofuranosyl-9H-purin-6-amineChEBI
9-beta-D-ArabinofuranosyladenineChEBI
SpongoadenosineChEBI
Vidarabine anhydrousKegg
ARA-aKegg
ArmesKegg
9-b-D-Arabinofuranosyl-9H-purin-6-amineGenerator
9-Β-D-arabinofuranosyl-9H-purin-6-amineGenerator
9-b-D-ArabinofuranosyladenineGenerator
9-Β-D-arabinofuranosyladenineGenerator
9-beta-D-Arabinofuranosyl-adenineHMDB
Adenine arabinosideHMDB
AraadenosineHMDB
Arabinoside adenineHMDB
Arabinosyl adenineHMDB
ArabinosyladenineHMDB
a, alpha-AraHMDB
Ara aHMDB
ArabinofuranosyladenineHMDB
Monarch brand OF vidarabineHMDB
ViraAHMDB
alpha Ara aHMDB
alpha D ArabinofuranosyladenineHMDB
alpha-Ara aHMDB
9 beta ArabinofuranosyladenineHMDB
9 beta D ArabinofuranosyladenineHMDB
a, AraHMDB
beta Ara aHMDB
Arabinoside, adenineHMDB
alpha-D-ArabinofuranosyladenineHMDB
9-beta-ArabinofuranosyladenineHMDB
a, beta-AraHMDB
Parke davis brand OF vidarabineHMDB
Vira aHMDB
Vira-aHMDB
beta-Ara aHMDB
VidarabineChEBI
Chemical FormulaC10H13N5O4
Average Molecular Weight267.2413
Monoisotopic Molecular Weight267.096753929
IUPAC Name(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional Namearmes
CAS Registry Number24356-66-9
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyOIRDTQYFTABQOQ-UHTZMRCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Primary alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point257.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point676.27 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility14 g/LNot Available
LogP-2.115Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available156.391http://allccs.zhulab.cn/database/detail?ID=AllCCS00001496
Predicted Molecular Properties
PropertyValueSource
Water Solubility14 g/LALOGPS
logP-1.2ALOGPS
logP-2.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m³·mol⁻¹ChemAxon
Polarizability24.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.87831661259
DarkChem[M-H]-153.57331661259
DeepCCS[M+H]+155.1830932474
DeepCCS[M-H]-152.78530932474
DeepCCS[M-2H]-187.11130932474
DeepCCS[M+Na]+162.07430932474
AllCCS[M+H]+160.432859911
AllCCS[M+H-H2O]+156.932859911
AllCCS[M+NH4]+163.732859911
AllCCS[M+Na]+164.632859911
AllCCS[M-H]-159.232859911
AllCCS[M+Na-2H]-158.732859911
AllCCS[M+HCOO]-158.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VidarabineNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O3472.6Standard polar33892256
VidarabineNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O1712.7Standard non polar33892256
VidarabineNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O2593.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vidarabine,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O)[C@@H]1O2670.2Semi standard non polar33892256
Vidarabine,1TMS,isomer #2C[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1CO2671.0Semi standard non polar33892256
Vidarabine,1TMS,isomer #3C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=CN=C212660.9Semi standard non polar33892256
Vidarabine,1TMS,isomer #4C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O2711.3Semi standard non polar33892256
Vidarabine,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O2605.5Semi standard non polar33892256
Vidarabine,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C2600.5Semi standard non polar33892256
Vidarabine,2TMS,isomer #3C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O2648.9Semi standard non polar33892256
Vidarabine,2TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=CN=C212607.3Semi standard non polar33892256
Vidarabine,2TMS,isomer #5C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O2651.8Semi standard non polar33892256
Vidarabine,2TMS,isomer #6C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C2640.9Semi standard non polar33892256
Vidarabine,2TMS,isomer #7C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C2659.3Semi standard non polar33892256
Vidarabine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2569.9Semi standard non polar33892256
Vidarabine,3TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C2621.9Semi standard non polar33892256
Vidarabine,3TMS,isomer #3C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O2617.5Semi standard non polar33892256
Vidarabine,3TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O2631.0Semi standard non polar33892256
Vidarabine,3TMS,isomer #5C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2621.6Semi standard non polar33892256
Vidarabine,3TMS,isomer #6C[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1CO2642.3Semi standard non polar33892256
Vidarabine,3TMS,isomer #7C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C212633.4Semi standard non polar33892256
Vidarabine,4TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2630.3Semi standard non polar33892256
Vidarabine,4TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2712.2Standard non polar33892256
Vidarabine,4TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3681.5Standard polar33892256
Vidarabine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O2642.5Semi standard non polar33892256
Vidarabine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O2784.1Standard non polar33892256
Vidarabine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O3406.1Standard polar33892256
Vidarabine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C2639.8Semi standard non polar33892256
Vidarabine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C2771.1Standard non polar33892256
Vidarabine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C3366.6Standard polar33892256
Vidarabine,4TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C212643.5Semi standard non polar33892256
Vidarabine,4TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C212795.9Standard non polar33892256
Vidarabine,4TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C213336.5Standard polar33892256
Vidarabine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2689.3Semi standard non polar33892256
Vidarabine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2768.0Standard non polar33892256
Vidarabine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3158.7Standard polar33892256
Vidarabine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O)[C@@H]1O2926.5Semi standard non polar33892256
Vidarabine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1CO2920.6Semi standard non polar33892256
Vidarabine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=CN=C212911.6Semi standard non polar33892256
Vidarabine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O2906.2Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3078.2Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3076.1Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O3062.2Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=CN=C213070.4Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3042.6Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3035.9Semi standard non polar33892256
Vidarabine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C3062.0Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3224.8Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3226.4Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3227.4Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O3221.6Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3212.1Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1CO3230.8Semi standard non polar33892256
Vidarabine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C213215.2Semi standard non polar33892256
Vidarabine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3402.4Semi standard non polar33892256
Vidarabine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3520.5Standard non polar33892256
Vidarabine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3871.2Standard polar33892256
Vidarabine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3369.8Semi standard non polar33892256
Vidarabine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3596.8Standard non polar33892256
Vidarabine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3644.5Standard polar33892256
Vidarabine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3376.3Semi standard non polar33892256
Vidarabine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3592.8Standard non polar33892256
Vidarabine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3618.2Standard polar33892256
Vidarabine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C213363.7Semi standard non polar33892256
Vidarabine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C213595.8Standard non polar33892256
Vidarabine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C213594.8Standard polar33892256
Vidarabine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3562.3Semi standard non polar33892256
Vidarabine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3694.1Standard non polar33892256
Vidarabine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3538.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vidarabine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9350000000-ed8639e5b54e468256282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vidarabine GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1492400000-1fe7f0d7ca11fdb4800f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vidarabine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vidarabine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vidarabine LC-ESI-qTof , Positive-QTOFsplash10-000i-2910000000-e18a8d00eb0e73aa6dec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vidarabine , positive-QTOFsplash10-000i-2910000000-e18a8d00eb0e73aa6dec2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 10V, Positive-QTOFsplash10-000i-0940000000-42bee9785f9b55b32eea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 20V, Positive-QTOFsplash10-000i-0900000000-c8cda6a661ace060572c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 40V, Positive-QTOFsplash10-000i-2900000000-0304a85c3951aa1cb41a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 10V, Negative-QTOFsplash10-0159-0690000000-0258e5851611884483d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 20V, Negative-QTOFsplash10-001i-0900000000-e6b8fc6980387f646d642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 40V, Negative-QTOFsplash10-053r-2900000000-1e0cad8d044715d90f122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 10V, Negative-QTOFsplash10-001i-0910000000-83e24e24fe97518d665a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 20V, Negative-QTOFsplash10-001i-0900000000-291c06f7d909185dce292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 40V, Negative-QTOFsplash10-053r-1900000000-1401974aef47ea042a5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 10V, Positive-QTOFsplash10-000i-0920000000-c89adfa0ec9ccc01f1312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 20V, Positive-QTOFsplash10-000i-0900000000-c1ee2199364d0258bae12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vidarabine 40V, Positive-QTOFsplash10-000i-1900000000-fd986996dd15b24690082021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00194 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00194 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00194
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID20400
KEGG Compound IDC07195
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVidarabine
METLIN IDNot Available
PubChem Compound21704
PDB IDRAB
ChEBI ID45327
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1666791
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Feher Z, Mishra NC: An aphidicolin-resistant mutant of Chinese hamster ovary cell with altered DNA polymerase and 3' exonuclease activities. Biochim Biophys Acta. 1995 Aug 22;1263(2):141-6. [PubMed:7640304 ]
  2. Russell RR 3rd, Bergeron R, Shulman GI, Young LH: Translocation of myocardial GLUT-4 and increased glucose uptake through activation of AMPK by AICAR. Am J Physiol. 1999 Aug;277(2 Pt 2):H643-9. [PubMed:10444490 ]
  3. Moore CL, Chiaramonte M, Higgins T, Kuchta RD: Synthesis of nucleotide analogues that potently and selectively inhibit human DNA primase. Biochemistry. 2002 Nov 26;41(47):14066-75. [PubMed:12437364 ]
  4. Kuchta RD, Ilsley D, Kravig KD, Schubert S, Harris B: Inhibition of DNA primase and polymerase alpha by arabinofuranosylnucleoside triphosphates and related compounds. Biochemistry. 1992 May 19;31(19):4720-8. [PubMed:1581321 ]
  5. Chen J, Hudson E, Chi MM, Chang AS, Moley KH, Hardie DG, Downs SM: AMPK regulation of mouse oocyte meiotic resumption in vitro. Dev Biol. 2006 Mar 15;291(2):227-38. Epub 2006 Jan 26. [PubMed:16443210 ]
  6. Thompson HC, Kuchta RD: Arabinofuranosyl nucleotides are not chain-terminators during initiation of new strands of DNA by DNA polymerase alpha-primase. Biochemistry. 1995 Sep 5;34(35):11198-203. [PubMed:7545435 ]
  7. Feher Z, Mishra NC: Aphidicolin-resistant Chinese hamster ovary cells possess altered DNA polymerases of the alpha-family. Biochim Biophys Acta. 1994 May 17;1218(1):35-47. [PubMed:7514891 ]

Enzymes

General function:
Involved in deaminase activity
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Molecular weight:
40764.13
References
  1. Agarwal RP, Blatt J, Miser J, Sallan S, Lipton JM, Reaman GH, Holcenberg J, Poplack DG: Clinical pharmacology of 9-beta-D-arabinofuranosyladenine in combination with 2'-deoxycoformycin. Cancer Res. 1982 Sep;42(9):3884-6. [PubMed:6980706 ]
  2. Balzarini J, De Clercq E: The antiviral activity of 9-beta-D-arabinofuranosyladenine is enhanced by the 2',3'-dideoxyriboside, the 2',3'-didehydro-2',3'-dideoxyriboside and the 3'-azido-2',3'-dideoxyriboside of 2,6-diaminopurine. Biochem Biophys Res Commun. 1989 Feb 28;159(1):61-7. [PubMed:2538128 ]
  3. Cristalli G, Franchetti P, Grifantini M, Vittori S, Lupidi G, Riva F, Bordoni T, Geroni C, Verini MA: Adenosine deaminase inhibitors. Synthesis and biological activity of deaza analogues of erythro-9-(2-hydroxy-3-nonyl)adenine. J Med Chem. 1988 Feb;31(2):390-3. [PubMed:3339608 ]