valganciclovir   Click here for help

GtoPdb Ligand ID: 4716

Synonyms: Ro-1079070/194 | RS-079070-194 | Valcyte®
Approved drug
valganciclovir is an approved drug (FDA (2002, prior history not available))
Compound class: Synthetic organic
Comment: Valcyte® contains valganciclovir hydrochloride (PubChem CID 110632). This is a prodrug of ganciclovir (PubChem CID 3454). The INN document for this drug specifies that there is a chiral centre at (position t8) and the INN-assigned compound consists of two epimers depending on the stereochemistry at this position. The structure shown here does not specify stereochemistry at this point and represents the mixture. This is represented by the '?' in the InChI standard identifier on the 'Structure' tab.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: valganciclovir

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 171.37
Molecular weight 354.17
XLogP 0.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES OCC(OCn1cnc2c1[nH]c(N)nc2=O)COC(=O)C(C(C)C)N
Isomeric SMILES OCC(OCn1cnc2c1[nH]c(N)nc2=O)COC(=O)[C@H](C(C)C)N
InChI InChI=1S/C14H22N6O5/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22)/t8?,9-/m0/s1
InChI Key WPVFJKSGQUFQAP-GKAPJAKFSA-N
References
1. Sugawara M, Huang W, Fei YJ, Leibach FH, Ganapathy V, Ganapathy ME. (2000)
Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2.
J Pharm Sci, 89 (6): 781-9. [PMID:10824137]
2. Umapathy NS, Ganapathy V, Ganapathy ME. (2004)
Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+).
Pharm Res, 21 (7): 1303-10. [PMID:15290873]
3. Ural-Blimke Y, Flayhan A, Strauss J, Rantos V, Bartels K, Nielsen R, Pardon E, Steyaert J, Kosinski J, Quistgaard EM et al.. (2019)
Structure of Prototypic Peptide Transporter DtpA from E. coli in Complex with Valganciclovir Provides Insights into Drug Binding of Human PepT1.
J Am Chem Soc, 141 (6): 2404-2412. [PMID:30644743]