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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015613
Secondary Accession Numbers
  • HMDB15613
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
Data?1582753316
Synonyms
ValueSource
Ecabet sodiumHMDB
12-Sulfodehydroabietic acidHMDB
1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-6-sulfO-1-phenanthrenecarboxylic acid 6-sodium saltHMDB
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 KeyIWCWQNVIUXZOMJ-MISYRCLQSA-N
Chemical Taxonomy
Description 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
  • Abietane diterpenoid
  • Diterpenoid
  • Hydrophenanthrene
  • Phenanthrene
  • Tetralin
  • 1-sulfo,2-unsubstituted aromatic compound
  • Arylsulfonic acid or derivatives
  • Benzenoid
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0043 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0043 g/LALOGPS
logP1.5ALOGPS
logP4.93ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.07 m³·mol⁻¹ChemAxon
Polarizability41.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.22831661259
DarkChem[M-H]-184.23231661259
DeepCCS[M-2H]-226.4930932474
DeepCCS[M+Na]+202.7230932474
AllCCS[M+H]+189.032859911
AllCCS[M+H-H2O]+186.432859911
AllCCS[M+NH4]+191.432859911
AllCCS[M+Na]+192.132859911
AllCCS[M-H]-193.032859911
AllCCS[M+Na-2H]-193.532859911
AllCCS[M+HCOO]-194.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ecabet[H][C@@]12CCC3=CC(C(C)C)=C(C=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)S(O)(=O)=O4729.4Standard polar33892256
Ecabet[H][C@@]12CCC3=CC(C(C)C)=C(C=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)S(O)(=O)=O2689.7Standard non polar33892256
Ecabet[H][C@@]12CCC3=CC(C(C)C)=C(C=C3[C@@]1(C)CCC[C@@]2(C)C(O)=O)S(O)(=O)=O3118.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ecabet,1TMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@@H]1CC23012.8Semi standard non polar33892256
Ecabet,1TMS,isomer #2CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O)[C@@H]1CC23054.8Semi standard non polar33892256
Ecabet,2TMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@@H]1CC22956.2Semi standard non polar33892256
Ecabet,2TMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@@H]1CC23182.5Standard non polar33892256
Ecabet,2TMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@@H]1CC23445.3Standard polar33892256
Ecabet,1TBDMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC23258.7Semi standard non polar33892256
Ecabet,1TBDMS,isomer #2CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O)[C@@H]1CC23289.2Semi standard non polar33892256
Ecabet,2TBDMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC23416.9Semi standard non polar33892256
Ecabet,2TBDMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC23705.4Standard non polar33892256
Ecabet,2TBDMS,isomer #1CC(C)C1=CC2=C(C=C1S(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1CC23614.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ecabet GC-MS (Non-derivatized) - 70eV, Positivesplash10-0i2c-0098000000-8616f99fe7bf5b6d3cf22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecabet GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-5009600000-09b033920fd770aab5352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecabet GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 10V, Positive-QTOFsplash10-01q9-0009000000-6c6e7efeb17e3ddff08d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 20V, Positive-QTOFsplash10-0gws-0298000000-bfea21abd97ffe77fe702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 40V, Positive-QTOFsplash10-0gb9-6392000000-7fa1bb2495b98264ae562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 10V, Negative-QTOFsplash10-004i-0009000000-c9f3d0b1ddc4027d2a842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 20V, Negative-QTOFsplash10-002r-1019000000-8486ba86bc8df2348a8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 40V, Negative-QTOFsplash10-001i-9032000000-ac5dddf82db200b216232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 10V, Positive-QTOFsplash10-000i-0019000000-5d1a6665c9017dade4e42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 20V, Positive-QTOFsplash10-000i-0098000000-a0f92753929735b5d1d12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 40V, Positive-QTOFsplash10-0udi-1290000000-34fa1f1e7c3c302480662021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 10V, Negative-QTOFsplash10-004i-0009000000-5a6d090cebfd7793f5222021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 20V, Negative-QTOFsplash10-004i-2019000000-1e05eee16560fd57ed6a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecabet 40V, Negative-QTOFsplash10-001i-9022000000-2f12176e3bed15ca411e2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05265 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05265 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05265
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59201
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65781
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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. [PubMed:15458921 ]