Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-06 15:16:50 UTC |
---|
Update Date | 2022-03-07 02:51:44 UTC |
---|
HMDB ID | HMDB0014770 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Docosanol |
---|
Description | Docosanol is a drug used for topical treatment for recurrent herpes simplex labialis episodes (episodes of cold sores or fever blisters). A saturated 22-carbon aliphatic alcohol, docosanol exhibits antiviral activity against many lipid enveloped viruses including herpes simplex virus (HSV). Docosanol inhibits fusion between the plasma membrane and the herpes simplex virus (HSV) envelope, thereby preventing viral entry into cells and subsequent viral replication. |
---|
Structure | 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 |
---|
Synonyms | Value | Source |
---|
1-Docosanol | ChEBI | Abreva | ChEBI | Behenic alcohol | ChEBI | Behenyl alcohol | ChEBI | Docosyl alcohol | ChEBI | N-Docosanol | ChEBI | Tadenan | ChEBI | IK.2 | MeSH, HMDB | Docosanol | ChEBI | 1-Docosonol | PhytoBank |
|
---|
Chemical Formula | C22H46O |
---|
Average Molecular Weight | 326.6 |
---|
Monoisotopic Molecular Weight | 326.354866094 |
---|
IUPAC Name | docosan-1-ol |
---|
Traditional Name | docosanol |
---|
CAS Registry Number | 30303-65-2 |
---|
SMILES | CCCCCCCCCCCCCCCCCCCCCCO |
---|
InChI Identifier | 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 |
---|
InChI Key | NOPFSRXAKWQILS-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty alcohols |
---|
Direct Parent | Fatty alcohols |
---|
Alternative Parents | |
---|
Substituents | - Fatty alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 65 - 72 °C | Not Available | Boiling Point | 375.00 to 376.00 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | Water Solubility | 2.0e-05 g/L | Not Available | LogP | 9 | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - Docosanol GC-MS (1 TMS) | splash10-001i-9404000000-07035644854a3aadee15 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Docosanol EI-B (Non-derivatized) | splash10-0a4l-9000000000-809da2804db4c444826e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Docosanol GC-MS (Non-derivatized) | splash10-001i-9404000000-07035644854a3aadee15 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosanol GC-MS (Non-derivatized) - 70eV, Positive | splash10-002g-3980000000-1de3f264f616e9cd2e99 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosanol GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9751000000-7ebe6c4d36a698fdfc80 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosanol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosanol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a5c-9100000000-e4725e578cce9e0d56c9 | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - Docosanol Linear Ion Trap , negative-QTOF | splash10-001i-0910000000-57263f402e03ec3b6118 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Docosanol Linear Ion Trap , negative-QTOF | splash10-001i-0910000000-8019512337243ed50237 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Docosanol Linear Ion Trap , positive-QTOF | splash10-001i-0292000000-dcde24f71302487910ab | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Docosanol Linear Ion Trap , positive-QTOF | splash10-03e9-0392000000-bc888101b8e5bdc1433c | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 10V, Positive-QTOF | splash10-0a6r-0019000000-4459327ac9264207c42b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 20V, Positive-QTOF | splash10-0a4i-4679000000-3b63e7998956cb76610d | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 40V, Positive-QTOF | splash10-052g-9780000000-e5c96bc23fb838664be8 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 10V, Negative-QTOF | splash10-004i-0019000000-e487b70d17ce877c4987 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 20V, Negative-QTOF | splash10-004i-1039000000-15751d0411e9ac8675f3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 40V, Negative-QTOF | splash10-002g-9683000000-535688ef71e2090b3c13 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 10V, Positive-QTOF | splash10-004i-1009000000-317011308993108a1f81 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 20V, Positive-QTOF | splash10-0a6r-9114000000-c006045c17813cdbbbe5 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 40V, Positive-QTOF | splash10-0a4l-9000000000-ec1360604f4e31b632f7 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 10V, Negative-QTOF | splash10-004i-0009000000-571dd37484b1ca831cc2 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 20V, Negative-QTOF | splash10-004i-0009000000-27e909050baaa941d5ff | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosanol 40V, Negative-QTOF | splash10-004i-7198000000-27d4ee678a45f6399c8a | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
|
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00632 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00632 | | details |
|
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | DB00632 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB007105 |
---|
KNApSAcK ID | C00030805 |
---|
Chemspider ID | 12100 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Docosanol |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 12620 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 31000 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | rw1153971 |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
---|