Structure Database (LMSD)

Common Name
Behenyl alcohol
Systematic Name
1-docosanol
Synonyms
  • docosan-1-ol
LM ID
LMFA05000008
Formula
C22H46O
Exact Mass
Calculate m/z
326.354866
Sum Composition
FOH 22:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty alcohols [FA05]

Biological Context

Docosanol is an aliphatic alcohol that has broad-spectrum antiviral activity against viruses with a lipid envelope (ID50s = 3-12 nM for inhibition of replication).1 It inhibits herpes simplex virus type 1 (HSV-1) replication and protein synthesis in Vero cells.2 It also inhibits HSV-2 plaque formation and virus production in wild-type Vero cells and cells resistant to acyclovir . Docosanol acts by prohibiting the HSV envelope from fusing with the plasma membrane.1 Formulations containing docosanol have been used in the topical treatment of HSV-1.

This information has been provided by Cayman Chemical

References

1. Katz, D.H., Marcelletti, J.F., Khalil, M.H., et al. Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex. Proc. Natl. Acad. Sci. USA 88(23), 10825-10829 (1991).
2. Pope, L.E., Marcelletti, J.F., Katz, L.R., et al. The anti-herpes simplex virus activity of n-docosanol includes inhibition of the viral entry process. Antiviral Res. 40(1-2), 85-94 (1998).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
1-Docosanol and other long chain primary alcohols in developing rat brain.,
Lipids, 1977
Pubmed ID: 834119

String Representations

InChiKey (Click to copy)
NOPFSRXAKWQILS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H46O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23/h23H,2-22H2,1H3
SMILES (Click to copy)
C(CCCCCCCCCCCCCO)CCCCCCCC

Other Databases

Wikipedia
Behenyl alcohol
HMDB ID
HMDB0014770
CHEBI ID
31000
PubChem CID
12620
SwissLipids ID
SLM:000001242
Cayman ID
23793

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 397.95
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 8.09
Molar Refractivity 105.59

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Created at
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Updated at
1st Jan 2025