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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:28 UTC
HMDB IDHMDB0015190
Secondary Accession Numbers
  • HMDB15190
Metabolite Identification
Common NameEchothiophate
DescriptionEchothiophate is only found in individuals that have used or taken this drug. It is a potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.Echothiophate Iodide is a long-acting cholinesterase inhibitor for topical use which enhances the effect of endogenously liberated acetylcholine in iris, ciliary muscle, and other parasympathetically innervated structures of the eye. Echothiophate iodide binds irreversibly to cholinesterase, and is long acting due to the slow rate of hydrolysis by cholinesterase. It causes miosis, increase in facility of outflow of aqueous humor, fall in intraocular pressure, and potentiation of accommodation.
Structure
Thumb
Synonyms
ValueSource
(2-Diethoxyphosphinylthioethyl)trimethylammoniumChEBI
EcothiopatumChEBI
Echothiophic acidGenerator
Echothiophate iodideHMDB
PhospholineHMDB
Phospholine iodideHMDB
Chemical FormulaC9H23NO3PS
Average Molecular Weight256.323
Monoisotopic Molecular Weight256.113625809
IUPAC Namediethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate
Traditional Nameechothiophate
CAS Registry Number6736-03-4
SMILES
CCOP(=O)(OCC)SCC[N+](C)(C)C
InChI Identifier
InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1
InChI KeyBJOLKYGKSZKIGU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentTetraalkylammonium salts
Alternative Parents
Substituents
  • Tetraalkylammonium salt
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organosulfur compound
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 g/LNot Available
LogP-2.25Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.14 m³·mol⁻¹ChemAxon
Polarizability27.65 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bti-9430000000-9a12a7daa0bdce2c4cbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0560-1290000000-868e033b143724b9541dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9120000000-e8acf122864e526e6d7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9300000000-ad757d7f51f1bc3cbf44View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01057 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01057 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01057
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10108
KEGG Compound IDC06975
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEchothiophate
METLIN IDNot Available
PubChem Compound10548
PDB IDNot Available
ChEBI ID4753
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. [PubMed:7166393 ]
  2. Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O: Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res. 2010 Aug;35(8):698-702. doi: 10.3109/02713681003794076. [PubMed:20673046 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Henderson EG, Post-Munson DJ, Reynolds LS, Epstein PM: Echothiophate and cogeners decrease the voltage dependence of end-plate current decay in frog skeletal muscle. J Pharmacol Exp Ther. 1989 Dec;251(3):810-6. [PubMed:2481033 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]