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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:29:11 UTC
HMDB IDHMDB14607
Secondary Accession NumbersNone
Metabolite Identification
Common NameSodium Tetradecyl Sulfate
DescriptionSodium Tetradecyl Sulfate is only found in individuals that have used or taken this drug. It is an anionic surface-active agent used for its wetting properties in industry and used in medicine as an irritant and sclerosing agent for hemorrhoids and varicose veins. Sodium tetradecyl sulfate is a potent toxin for endothelial cells in that brief exposure to even low concentrations are effective in stripping endothelium over a considerable distance and exposing highly thrombogenic endothelium in the process. Diluted sodium tetradecyl sulfate is also able to induce a hypercoagulable state, possibly by selective inhibition of protein C, and can also promote platelet aggregation.
Structure
Thumb
Synonyms
ValueSource
Monotetradecylsulfate sodium saltHMDB
Monotetradecylsulphate sodium saltHMDB
S.T.D.HMDB
Sodium myristyl sulfateHMDB
Sodium myristyl sulphateHMDB
Tetradecyl hydrogen sulfateHMDB
Tetradecyl hydrogen sulphateHMDB
Tetradecyl sodium sulfateHMDB
Tetradecyl sodium sulphateHMDB
Tetradecyl sulfateHMDB
Tetradecyl sulfuric acidHMDB
Tetradecyl sulphateHMDB
Chemical FormulaC14H29NaO4S
Average Molecular Weight316.432
Monoisotopic Molecular Weight316.168424781
IUPAC Namesodium tetradecyl sulfate
Traditional Namesodium tetradecyl sulfate
CAS Registry Number1191-50-0
SMILES
[Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O
InChI Identifier
InChI=1S/C14H30O4S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-19(15,16)17;/h2-14H2,1H3,(H,15,16,17);/q;+1/p-1
InChI KeyInChIKey=UPUIQOIQVMNQAP-UHFFFAOYSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassSulfuric acid esters
Direct ParentSulfuric acid monoesters
Alternative Parents
Substituents
  • Sulfuric acid monoester
  • Alkyl sulfate
  • Sulfate-ester
  • Hydrocarbon derivative
  • Organic alkali metal salt
  • Organic sodium salt
  • Organic salt
  • Organooxygen compound
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Sclerosing Agents
  • Surface-Active Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.62e-03 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0064 mg/mLALOGPS
logP4.61ALOGPS
logP5.31ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.01 m3·mol-1ChemAxon
Polarizability35.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00464
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00464
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00464
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5058
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB14607
Metagene LinkHMDB14607
METLIN IDNot Available
PubChem Compound5248
PDB IDNot Available
ChEBI ID782257
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Protein C is a vitamin K-dependent serine protease that regulates blood coagulation by inactivating factors Va and VIIIa in the presence of calcium ions and phospholipids
Gene Name:
PROC
Uniprot ID:
P04070
Molecular weight:
52070.8
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  2. Jacobson BF, Franz RC, Hurly EM, Norman GL, Becker P, Myburgh JA, Mendelow BV: Mechanism of thrombosis caused by sclerotherapy of esophageal varices using sodium tetradecyl sulphate. Surg Endosc. 1992 Jan-Feb;6(1):4-9. [1344580 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  4. Parsi K, Exner T, Low J, Ma DD, Joseph JE: In vitro effects of detergent sclerosants on antithrombotic mechanisms. Eur J Vasc Endovasc Surg. 2009 Aug;38(2):220-8. Epub 2009 May 12. [19442540 ]
General function:
Involved in calcium ion binding
Specific function:
Anticoagulant plasma protein; it is a cofactor to activated protein C in the degradation of coagulation factors Va and VIIIa. It helps to prevent coagulation and stimulating fibrinolysis
Gene Name:
PROS1
Uniprot ID:
P07225
Molecular weight:
75121.9
References
  1. Parsi K, Exner T, Low J, Ma DD, Joseph JE: In vitro effects of detergent sclerosants on antithrombotic mechanisms. Eur J Vasc Endovasc Surg. 2009 Aug;38(2):220-8. Epub 2009 May 12. [19442540 ]
  2. Jacobson BF, Franz RC, Hurly EM, Norman GL, Becker P, Myburgh JA, Mendelow BV: Mechanism of thrombosis caused by sclerotherapy of esophageal varices using sodium tetradecyl sulphate. Surg Endosc. 1992 Jan-Feb;6(1):4-9. [1344580 ]