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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:43 UTC
HMDB IDHMDB0014716
Secondary Accession Numbers
  • HMDB14716
Metabolite Identification
Common NameValaciclovir
DescriptionValaciclovir, also known as valtrex or L-valylacyclovir, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Valaciclovir is a very strong basic compound (based on its pKa). Valaciclovir is a potentially toxic compound. Valaciclovir was patented in 1987 and came into medical use in 1995. In the United States the wholesale cost of this amount is about US$2.80. Infrequent adverse effects (0.1–1% of patients) include: agitation, vertigo, confusion, dizziness, edema, arthralgia, sore throat, constipation, abdominal pain, rash, weakness and/or renal impairment.
Structure
Data?1582753212
Synonyms
ValueSource
L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanineChEBI
L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl esterChEBI
ValacyclovirKegg
ValtrexKegg
Valacyclover hydrochloricHMDB
Valacyclovir hydrochlorideHMDB
Valacyclovir, (D)-isomerHMDB
Valacyclovir, (L)-isomerHMDB
2-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl L-valinateHMDB
Valacyclovir hydrochloride, (DL)-isomerHMDB
Valacyclovir, X-hydrochloride, (D)-isomerHMDB
Valacyclovir, X-hydrochloride, (DL)-isomerHMDB
L-ValylacyclovirHMDB
Acyclovir, L-valyl esterHMDB
Valacyclovir, (DL)-isomerHMDB
ValaciclovirMeSH
Chemical FormulaC13H20N6O4
Average Molecular Weight324.3357
Monoisotopic Molecular Weight324.154603158
IUPAC Name2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
Traditional Namevaltrex
CAS Registry Number124832-27-5
SMILES
CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O
InChI Identifier
InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
InChI KeyHDOVUKNUBWVHOX-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Valine or derivatives
  • 6-oxopurine
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Fatty acid ester
  • N-substituted imidazole
  • Pyrimidine
  • Fatty acyl
  • Azole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.55 g/LNot Available
LogP-0.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.55 g/LALOGPS
logP-0.84ALOGPS
logP-0.45ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)7.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area146.85 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity80.63 m³·mol⁻¹ChemAxon
Polarizability31.96 ųChemAxon
Number of Rings2ChemAxon
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]+176.57931661259
DarkChem[M-H]-172.28431661259
DeepCCS[M+H]+167.60830932474
DeepCCS[M-H]-165.2530932474
DeepCCS[M-2H]-198.71330932474
DeepCCS[M+Na]+173.9430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ValaciclovirCC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O3527.6Standard polar33892256
ValaciclovirCC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O2674.8Standard non polar33892256
ValaciclovirCC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O3098.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valaciclovir,1TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O2840.2Semi standard non polar33892256
Valaciclovir,1TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O2829.3Standard non polar33892256
Valaciclovir,1TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O4897.6Standard polar33892256
Valaciclovir,1TMS,isomer #2CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O2873.0Semi standard non polar33892256
Valaciclovir,1TMS,isomer #2CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O3022.2Standard non polar33892256
Valaciclovir,1TMS,isomer #2CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O5316.5Standard polar33892256
Valaciclovir,1TMS,isomer #3CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O2882.3Semi standard non polar33892256
Valaciclovir,1TMS,isomer #3CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O2976.1Standard non polar33892256
Valaciclovir,1TMS,isomer #3CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O5358.7Standard polar33892256
Valaciclovir,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O2831.2Semi standard non polar33892256
Valaciclovir,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O2884.8Standard non polar33892256
Valaciclovir,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O4564.1Standard polar33892256
Valaciclovir,2TMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C2914.1Semi standard non polar33892256
Valaciclovir,2TMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C2962.4Standard non polar33892256
Valaciclovir,2TMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C4643.8Standard polar33892256
Valaciclovir,2TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O2832.0Semi standard non polar33892256
Valaciclovir,2TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O2825.9Standard non polar33892256
Valaciclovir,2TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O4632.2Standard polar33892256
Valaciclovir,2TMS,isomer #4CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O2826.6Semi standard non polar33892256
Valaciclovir,2TMS,isomer #4CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O3094.3Standard non polar33892256
Valaciclovir,2TMS,isomer #4CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O4923.7Standard polar33892256
Valaciclovir,2TMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O2847.1Semi standard non polar33892256
Valaciclovir,2TMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O3023.2Standard non polar33892256
Valaciclovir,2TMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O4903.6Standard polar33892256
Valaciclovir,3TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C2981.8Semi standard non polar33892256
Valaciclovir,3TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C2994.9Standard non polar33892256
Valaciclovir,3TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C4213.3Standard polar33892256
Valaciclovir,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O2834.2Semi standard non polar33892256
Valaciclovir,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O2972.8Standard non polar33892256
Valaciclovir,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O4038.0Standard polar33892256
Valaciclovir,3TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O2866.6Semi standard non polar33892256
Valaciclovir,3TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O2887.2Standard non polar33892256
Valaciclovir,3TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O4074.9Standard polar33892256
Valaciclovir,3TMS,isomer #4CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3022.8Semi standard non polar33892256
Valaciclovir,3TMS,isomer #4CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C2954.3Standard non polar33892256
Valaciclovir,3TMS,isomer #4CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C4444.8Standard polar33892256
Valaciclovir,3TMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O2879.0Semi standard non polar33892256
Valaciclovir,3TMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O3115.7Standard non polar33892256
Valaciclovir,3TMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O4550.3Standard polar33892256
Valaciclovir,4TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3041.3Semi standard non polar33892256
Valaciclovir,4TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3112.3Standard non polar33892256
Valaciclovir,4TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3750.3Standard polar33892256
Valaciclovir,4TMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3078.9Semi standard non polar33892256
Valaciclovir,4TMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3019.3Standard non polar33892256
Valaciclovir,4TMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3794.3Standard polar33892256
Valaciclovir,4TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O2928.1Semi standard non polar33892256
Valaciclovir,4TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O3002.6Standard non polar33892256
Valaciclovir,4TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O3644.9Standard polar33892256
Valaciclovir,5TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3161.6Semi standard non polar33892256
Valaciclovir,5TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3142.1Standard non polar33892256
Valaciclovir,5TMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)[Si](C)(C)C3414.3Standard polar33892256
Valaciclovir,1TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O3035.2Semi standard non polar33892256
Valaciclovir,1TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O3023.0Standard non polar33892256
Valaciclovir,1TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O4817.0Standard polar33892256
Valaciclovir,1TBDMS,isomer #2CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O3040.0Semi standard non polar33892256
Valaciclovir,1TBDMS,isomer #2CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O3222.4Standard non polar33892256
Valaciclovir,1TBDMS,isomer #2CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O5204.2Standard polar33892256
Valaciclovir,1TBDMS,isomer #3CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O3023.1Semi standard non polar33892256
Valaciclovir,1TBDMS,isomer #3CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O3158.9Standard non polar33892256
Valaciclovir,1TBDMS,isomer #3CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O5240.6Standard polar33892256
Valaciclovir,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O3192.9Semi standard non polar33892256
Valaciclovir,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O3254.2Standard non polar33892256
Valaciclovir,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O4409.2Standard polar33892256
Valaciclovir,2TBDMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3291.4Semi standard non polar33892256
Valaciclovir,2TBDMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3300.0Standard non polar33892256
Valaciclovir,2TBDMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4524.3Standard polar33892256
Valaciclovir,2TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O3199.2Semi standard non polar33892256
Valaciclovir,2TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O3197.5Standard non polar33892256
Valaciclovir,2TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O4513.2Standard polar33892256
Valaciclovir,2TBDMS,isomer #4CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3180.9Semi standard non polar33892256
Valaciclovir,2TBDMS,isomer #4CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3457.1Standard non polar33892256
Valaciclovir,2TBDMS,isomer #4CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O4744.0Standard polar33892256
Valaciclovir,2TBDMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O3217.4Semi standard non polar33892256
Valaciclovir,2TBDMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O3390.8Standard non polar33892256
Valaciclovir,2TBDMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O4735.2Standard polar33892256
Valaciclovir,3TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3518.8Semi standard non polar33892256
Valaciclovir,3TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3546.7Standard non polar33892256
Valaciclovir,3TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4175.6Standard polar33892256
Valaciclovir,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3375.0Semi standard non polar33892256
Valaciclovir,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3532.4Standard non polar33892256
Valaciclovir,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O4035.6Standard polar33892256
Valaciclovir,3TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O3411.3Semi standard non polar33892256
Valaciclovir,3TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O3437.9Standard non polar33892256
Valaciclovir,3TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O4045.0Standard polar33892256
Valaciclovir,3TBDMS,isomer #4CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3570.3Semi standard non polar33892256
Valaciclovir,3TBDMS,isomer #4CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3467.1Standard non polar33892256
Valaciclovir,3TBDMS,isomer #4CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4350.7Standard polar33892256
Valaciclovir,3TBDMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3403.6Semi standard non polar33892256
Valaciclovir,3TBDMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3635.3Standard non polar33892256
Valaciclovir,3TBDMS,isomer #5CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O4411.3Standard polar33892256
Valaciclovir,4TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3720.6Semi standard non polar33892256
Valaciclovir,4TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3794.9Standard non polar33892256
Valaciclovir,4TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1[NH]C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3899.9Standard polar33892256
Valaciclovir,4TBDMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3773.7Semi standard non polar33892256
Valaciclovir,4TBDMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3682.2Standard non polar33892256
Valaciclovir,4TBDMS,isomer #2CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3931.0Standard polar33892256
Valaciclovir,4TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3606.7Semi standard non polar33892256
Valaciclovir,4TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3650.1Standard non polar33892256
Valaciclovir,4TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O3842.7Standard polar33892256
Valaciclovir,5TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3977.2Semi standard non polar33892256
Valaciclovir,5TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3883.8Standard non polar33892256
Valaciclovir,5TBDMS,isomer #1CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3724.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Valaciclovir GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9210000000-51af1895b699048675822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valaciclovir GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valaciclovir 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 - Valaciclovir , positive-QTOFsplash10-0udi-1910000000-3db14f76ba496cea0d812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valaciclovir 35V, Positive-QTOFsplash10-0udi-2900000000-a3e92ac9125245cf55132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valaciclovir 35V, Negative-QTOFsplash10-016r-0910000000-01375a23cf811e488a212021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 10V, Positive-QTOFsplash10-0udi-1913000000-e8d1da3daee2d76377832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 20V, Positive-QTOFsplash10-0udi-2900000000-90825e6bac8b121f346e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 40V, Positive-QTOFsplash10-0zg0-2900000000-9ced6b2b253471425de02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 10V, Negative-QTOFsplash10-00xs-5913000000-05fdd28b28d4365d3f852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 20V, Negative-QTOFsplash10-106s-5922000000-36d450a0ce5422cc73d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 40V, Negative-QTOFsplash10-0pbc-5900000000-8eaf432e968b85e4cb9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 10V, Positive-QTOFsplash10-0fb9-0926000000-779dfd0f2b063ec5e6c42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 20V, Positive-QTOFsplash10-0udi-0901000000-0d030c844b5ab6d9d46d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 40V, Positive-QTOFsplash10-000i-2900000000-7c25463514f877a340432021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 10V, Negative-QTOFsplash10-00di-0359000000-0a84f61843d1db09c7762021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 20V, Negative-QTOFsplash10-0udi-2920000000-8736ab32172119625d462021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valaciclovir 40V, Negative-QTOFsplash10-0k9x-5900000000-21c409fb0971f216644d2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00577 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00577 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00577
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54770
KEGG Compound IDC07184
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValacyclovir
METLIN IDNot Available
PubChem Compound60773
PDB IDNot Available
ChEBI ID35854
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [PubMed:2653790 ]
  2. Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. [PubMed:15290873 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH: Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun. 1998 May 19;246(2):470-5. [PubMed:9610386 ]
  2. Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [PubMed:9706043 ]
  3. Balimane PV, Tamai I, Guo A, Nakanishi T, Kitada H, Leibach FH, Tsuji A, Sinko PJ: Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun. 1998 Sep 18;250(2):246-51. [PubMed:9753615 ]
  4. Sawada K, Terada T, Saito H, Hashimoto Y, Inui KI: Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2. J Pharmacol Exp Ther. 1999 Nov;291(2):705-9. [PubMed:10525090 ]
  5. Balimane P, Sinko P: Effect of ionization on the variable uptake of valacyclovir via the human intestinal peptide transporter (hPepT1) in CHO cells. Biopharm Drug Dispos. 2000 Jul;21(5):165-74. [PubMed:11180195 ]
  6. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH: Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun. 1998 May 19;246(2):470-5. [PubMed:9610386 ]
  2. Sawada K, Terada T, Saito H, Hashimoto Y, Inui KI: Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2. J Pharmacol Exp Ther. 1999 Nov;291(2):705-9. [PubMed:10525090 ]