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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:35 UTC
HMDB IDHMDB15613
Secondary Accession NumbersNone
Metabolite Identification
Common NameEcabet
DescriptionEcabet is a prescription eye drop for the treatment of dry eye syndrome. Ecabet represents a new class of molecules that increases the quantity and quality of mucin produced by conjunctival goblet cells and corneal epithelia. Mucin is a glycoprotein component of tear film that lubricates while retarding moisture loss from tear evaporation. Ecabet is currently marketed in Japan as an oral agent for treatment of gastric ulcers and gastritis.
Structure
Thumb
Synonyms
ValueSource
Ecabet sodiumChEMBL
Chemical FormulaC20H28O5S
Average Molecular Weight380.498
Monoisotopic Molecular Weight380.165744696
IUPAC Name(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-6-sulfo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
Traditional Nameecabet
CAS Registry Number86408-72-2
SMILES
[H][C@@]12CCC3=CC(C(C)C)=C(C=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)S(O)(=O)=O
InChI Identifier
InChI=1S/C20H28O5S/c1-12(2)14-10-13-6-7-17-19(3,8-5-9-20(17,4)18(21)22)15(13)11-16(14)26(23,24)25/h10-12,17H,5-9H2,1-4H3,(H,21,22)(H,23,24,25)/t17-,19-,20-/m1/s1
InChI KeyInChIKey=IWCWQNVIUXZOMJ-MISYRCLQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Abietane diterpenoid
  • Phenanthrene
  • Hydrophenanthrene
  • Tetralin
  • 1-sulfo,2-unsubstituted aromatic compound
  • Cumene
  • Arylsulfonic acid or derivatives
  • Benzenoid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
  • Anti-Ulcer Agents
  • Anticarcinogenic Agents
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Protease Inhibitors
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.26e-03 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0043 mg/mLALOGPS
logP1.5ALOGPS
logP4.93ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.07 m3·mol-1ChemAxon
Polarizability41.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05265
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05265
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05265
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59201
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB15613
Metagene LinkHMDB15613
METLIN IDNot Available
PubChem Compound65781
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in protein binding
Specific function:
Constitutively potentiates the superoxide-generating activity of NOX1 and NOX3 and is required for the biogenesis of otoconia/otolith, which are crystalline structures of the inner ear involved in the perception of gravity. Isoform 3 is more potent than isoform 1 in activating NOX3. Together with NOXA1, may also substitute to NCF1/p47phox and NCF2/p67phox in supporting the phagocyte NOX2/gp91phox superoxide-generating activity
Gene Name:
NOXO1
Uniprot ID:
Q8NFA2
Molecular weight:
41252.3
References
  1. Kusumoto K, Kawahara T, Kuwano Y, Teshima-Kondo S, Morita K, Kishi K, Rokutan K: Ecabet sodium inhibits Helicobacter pylori lipopolysaccharide-induced activation of NADPH oxidase 1 or apoptosis of guinea pig gastric mucosal cells. Am J Physiol Gastrointest Liver Physiol. 2005 Feb;288(2):G300-7. Epub 2004 Sep 30. [15458921 ]