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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:33:04 UTC
Update Date2021-09-14 14:57:39 UTC
HMDB IDHMDB0060543
Secondary Accession Numbers
  • HMDB60543
Metabolite Identification
Common Name6-Hydroxyetodolac
Description6-Hydroxyetodolac belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. 6-Hydroxyetodolac is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866074
SynonymsNot Available
Chemical FormulaC17H21NO4
Average Molecular Weight303.3529
Monoisotopic Molecular Weight303.147058165
IUPAC Name2-{1,8-diethyl-6-hydroxy-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
Traditional Name{1,8-diethyl-6-hydroxy-3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
CAS Registry NumberNot Available
SMILES
CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C1
InChI Identifier
InChI=1S/C17H21NO4/c1-3-10-7-11(19)8-13-12-5-6-22-17(4-2,9-14(20)21)16(12)18-15(10)13/h7-8,18-19H,3-6,9H2,1-2H3,(H,20,21)
InChI KeyGQHWDDBALZVXBU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.7ALOGPS
logP3.14ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.55 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.14 m³·mol⁻¹ChemAxon
Polarizability33.02 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]+170.94731661259
DarkChem[M-H]-172.15431661259
DeepCCS[M+H]+180.01530932474
DeepCCS[M-H]-177.65730932474
DeepCCS[M-2H]-210.54430932474
DeepCCS[M+Na]+186.10830932474
AllCCS[M+H]+171.832859911
AllCCS[M+H-H2O]+168.432859911
AllCCS[M+NH4]+174.932859911
AllCCS[M+Na]+175.832859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-177.332859911
AllCCS[M+HCOO]-177.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-HydroxyetodolacCCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C14050.7Standard polar33892256
6-HydroxyetodolacCCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C12531.1Standard non polar33892256
6-HydroxyetodolacCCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C12858.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Hydroxyetodolac,1TMS,isomer #1CCC1=CC(O)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2678.8Semi standard non polar33892256
6-Hydroxyetodolac,1TMS,isomer #2CCC1=CC(O[Si](C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O2733.5Semi standard non polar33892256
6-Hydroxyetodolac,1TMS,isomer #3CCC1=CC(O)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O2764.8Semi standard non polar33892256
6-Hydroxyetodolac,2TMS,isomer #1CCC1=CC(O[Si](C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2710.9Semi standard non polar33892256
6-Hydroxyetodolac,2TMS,isomer #2CCC1=CC(O)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2719.0Semi standard non polar33892256
6-Hydroxyetodolac,2TMS,isomer #3CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O2801.5Semi standard non polar33892256
6-Hydroxyetodolac,3TMS,isomer #1CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2785.9Semi standard non polar33892256
6-Hydroxyetodolac,3TMS,isomer #1CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2637.3Standard non polar33892256
6-Hydroxyetodolac,3TMS,isomer #1CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2855.7Standard polar33892256
6-Hydroxyetodolac,1TBDMS,isomer #1CCC1=CC(O)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C2944.7Semi standard non polar33892256
6-Hydroxyetodolac,1TBDMS,isomer #2CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O2983.2Semi standard non polar33892256
6-Hydroxyetodolac,1TBDMS,isomer #3CCC1=CC(O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O2971.8Semi standard non polar33892256
6-Hydroxyetodolac,2TBDMS,isomer #1CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C3157.8Semi standard non polar33892256
6-Hydroxyetodolac,2TBDMS,isomer #2CCC1=CC(O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C3133.7Semi standard non polar33892256
6-Hydroxyetodolac,2TBDMS,isomer #3CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O3192.3Semi standard non polar33892256
6-Hydroxyetodolac,3TBDMS,isomer #1CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C3339.1Semi standard non polar33892256
6-Hydroxyetodolac,3TBDMS,isomer #1CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C3224.4Standard non polar33892256
6-Hydroxyetodolac,3TBDMS,isomer #1CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C3155.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyetodolac GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-4390000000-28acab85523823eedbdc2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyetodolac GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2126900000-0e248492895b2eea88592017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyetodolac GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Hydroxyetodolac 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 - 6-Hydroxyetodolac 10V, Positive-QTOFsplash10-000i-0092000000-7d39a27e28deeba327702017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Positive-QTOFsplash10-0k9l-0290000000-e8a5307b083be332bacb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Positive-QTOFsplash10-0c09-1910000000-7a1083d040220cfda6132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 10V, Negative-QTOFsplash10-0pb9-0095000000-061349fb9a57097cdbba2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Negative-QTOFsplash10-0k9x-0091000000-c4910da12bf690da91c22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Negative-QTOFsplash10-00di-0890000000-8f1d7a5126d1f40a5a132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 10V, Positive-QTOFsplash10-0udr-0079000000-6c0f3c7e90749e4966712021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Positive-QTOFsplash10-0zg3-0092000000-f29c01cc188f2ad883912021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Positive-QTOFsplash10-0550-0950000000-694bd08d8a43c121852d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 10V, Negative-QTOFsplash10-0udi-0019000000-41e8b9873576a95f56d62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Negative-QTOFsplash10-0zfr-0097000000-4761ff4c13eef5bdf7cc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Negative-QTOFsplash10-0udl-5598000000-c2d358ad89e2fc68a8b42021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14146232
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 ReferencesNot Available