Aciclovir
Athanor · official
C8H11N5O3 · 225.2 g/mol
IUPAC name: 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one
Also called acyclovir, Zovirax, herpes
WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one
- Synonyms
- acyclovir, Zovirax, herpes
+ 37 more
Acycloguanosine, 9-[(2-Hydroxyethoxy)methyl]guanine, Virorax, Vipral, Wellcome-248U, Aciclovirum, Sitavig, Acicloftal, Cargosil, Gerpevir, Aciclovirum [Latin], Novirus, BW-248U, 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one, 9-((2-Hydroxyethoxy)methyl)guanine, CHEBI:2453, Cyclovir, NSC-758477, 2-Amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-6H-purin-6-one, 2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one, DTXSID1022556, 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-, X4HES1O11F, NSC-645011, AVACLYR, NSC645011, 9-[(2-Hydroxyethoxy)-methyl]guanine, DTXCID102556, 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-, Aciclovirum (Latin), 2-amino-9-((2-hydroxyethoxy)methyl)-1,9-dihydro-6H-purin-6-one, 9-((2-Hydroxyethoxy)-methyl)guanine, Aclovir, Clearsore, Duvimex
- Molecular formula
- C8H11N5O3
- Empirical formula
- C8H11N5O3
- Molecular weight
- 225.2 g/mol
- Exact mass
- 225.08619
- CAS number
- 59277-89-3
- PubChem CID
- 135398513
- Canonical SMILES
- C1=NC2=C(N1COCCO)N=C(NC2=O)N
- Isomeric SMILES
- C1=NC2=C(N1COCCO)N=C(NC2=O)N
- InChI
- InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)
- InChIKey
- MKUXAQIIEYXACX-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Physical properties
- Appearance
- Crystals from ethanol[1]
2 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source –shown Crystals from ethanol [1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. V2: 76 – White, crystalline powder [1] Hazardous Substances Data Bank (HSDB)cites Physicians Desk Reference 67th ed. PDR Network, LLC, Montvale, NJ. p. 1203 (2013) - Solubility in water
- 0.2 mg/mL in alcohol[1]
2 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source – In water, 1,620 mg/L at 25 °C [1] Hazardous Substances Data Bank (HSDB)cites Kristl A et al; Pharmazie 48: 608-10 (1993) –shown 0.2 mg/mL in alcohol [1] Hazardous Substances Data Bank (HSDB)cites McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2092 - log P
- log Kow = -1.56[1]
- pKa
- pKa1= 2.27[1]
2 values
Only one source reports it.
Value As written Source –shown pKa1= 2.27 [1] Hazardous Substances Data Bank (HSDB)cites Physicians Desk Reference 67th ed. PDR Network, LLC, Montvale, NJ. p. 1203 (2013) – pKa2 = 9.25 [1] Hazardous Substances Data Bank (HSDB)cites Physicians Desk Reference 67th ed. PDR Network, LLC, Montvale, NJ. p. 1203 (2013)
Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.
Calculated
- Heavy atoms
- 16
- Rings
- 2
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.38
- H-bond donors
- 3
- H-bond acceptors
- 6 computed here · PubChem 5
- Rotatable bonds
- 4
- TPSA (Ų)
- 119 computed here · PubChem 115
- Formal charge
- 0
- XLogP3
- -1.9 PubChem
- Complexity
- 308 PubChem
- Stereocenters
- None
- 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
- C42.67%
- H4.92%
- N31.10%
- O21.31%
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
- -1.33 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -0.55 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.77 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 225.21
- log P ≤ 5 (Crippen): -1.33
- H-bond donors ≤ 5: 3
- H-bond acceptors ≤ 10: 6
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
Most widely reported: 95 company reports to ECHA. Source [2].
- Harmful or irritant
- H315Causes skin irritation (77.9% of reports)
- H319Causes serious eye irritation (77.9% of reports)
- H335May cause respiratory irritation (71.6% of reports)
Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
View all classifications (3)
- [2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 14.7% (14 of 95) of reports.
- [2] European Chemicals Agency (ECHA) · 95 reports · WarningH315, H319, H335
- [2] European Chemicals Agency (ECHA) · 40 reports · WarningH302, H312, H351
Storage
- Keep container tightly closed in a dry and well-ventilated place.[1]
Safety data sheets on the supplier’s page: LGC Standards, CATO Research Chemicals Inc., TimTec.
Always read the supplier’s safety data sheet before working with it.
Spectra
- NMRNMRShiftDB
- 13C NMRSpectraBase
- GC-MSNIST Mass Spectrometry Data Center · SpectraBase (DI/MS)
- MS-MSHuman Metabolome Database (HMDB) (LC-ESI-qTof · Positive) · Human Metabolome Database (HMDB) (LC-ESI-QQ · negative) · Human Metabolome Database (HMDB) (LC-ESI-QQ · negative) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive)
- LC-MSMassBank Europe (Exploris 480 Orbitrap (Thermo Scientific) · LC-ESI-QFT · POSITIVE) · MassBank Europe (Exploris 480 Orbitrap (Thermo Scientific) · LC-ESI-QFT · NEGATIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE)
- ATR-IRSpectraBase (Bio-Rad FTS · ATR-Neat (DuraSamplIR II))
- RamanSpectraBase (FT-Raman)
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]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
- [4]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [5]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [6]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [7]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [8]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.