Valaciclovir

Athanor · official

C₁₃H₂₀N₆O₄ · 324.34 g/mol

IUPAC name: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate

Also called valacyclovir, Valtrex, prodrug

Drugs Rings

Open in Athanor

Drawn from its SMILES with RDKit

WarningHarmful if swallowed

Names and identifiers

IUPAC name: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
Synonyms: valacyclovir, Valtrex, prodrug
+ 36 more
ValACV, Zelitrex, Val-ACV, L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine, L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester, MZ1IW7Q79D, DTXSID1023732, CHEBI:35854, L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, 2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate, Valaciclovirum, L-valylacyclovir, L Valylacyclovir, 2-((2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy)ethyl (2S)-2-amino-3-methylbutanoate, L-valyl Ester Acyclovir, RefChem:56196, acyclovir, L-valyl ester, Acyclovir, L valyl Ester, DTXCID403732, J05AB11, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl L-valinate, 603-015-6, 658-047-3, Valcyclovir, Valaciclovir (INN), Valtrex (TN), CHEMBL1349, 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate, 256U87 HCl, 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate, Valcivir, VALACICLOVIR [INN], 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate, Valaciclovir [INN:BAN], Talavir, Virval
Molecular formula: C₁₃H₂₀N₆O₄
Empirical formula: C₁₃H₂₀N₆O₄
Molecular weight: 324.34 g/mol
Exact mass: 324.15460
CAS number: 124832-26-4
PubChem CID: 135398742
Canonical SMILES: CC(C)C(C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N
Isomeric SMILES: CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N
InChI: 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
InChIKey: HDOVUKNUBWVHOX-QMMMGPOBSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 23
Rings: 2
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.54
H-bond donors: 3
H-bond acceptors: 8 computed here · PubChem 7
Rotatable bonds: 7 computed here · PubChem 8
TPSA (Å²): 151.1 computed here · PubChem 147
Formal charge: 0
XLogP3: -0.9 PubChem
Complexity: 483 PubChem
Stereocenters: 1 definedCIP: C4: S
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C48.14%
H6.22%
N25.91%
O19.73%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: -0.8 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.18 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.26 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 324.34
log P ≤ 5 (Crippen): -0.8
H-bond donors ≤ 5: 3
H-bond acceptors ≤ 10: 8

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

From European Chemicals Agency (ECHA). Source [2].

Harmful or irritant

H302Harmful if swallowed

Precautionary statements: P264, P270, P301+P317, P330, P501

View all classifications (2)

[2] European Chemicals Agency (ECHA) · WarningH302
[2] European Chemicals Agency (ECHA) · WarningH302

Storage

Store at 15 deg to 25 °C (59 deg to 77 °F). Dispense in a well-closed container as defined in the USP.[1]

Safety data sheets on the supplier’s page: DC Chemicals, Angene Chemical, Enamine.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.