Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014887
Secondary Accession Numbers
  • HMDB14887
Metabolite Identification
Common NameEtodolac
DescriptionEtodolac is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic and antipyretic properties. Its therapeutic effects are due to its ability to inhibit prostaglandin synthesis. It is indicated for relief of signs and symptoms of rheumatoid arthritis and osteoarthritis. Similar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 – 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.
Structure
Data?1582753231
Synonyms
ValueSource
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidChEBI
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acidChEBI
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acidChEBI
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidChEBI
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acidChEBI
EtodolacoChEBI
EtodolacumChEBI
ETODOLIC ACIDChEBI
LodineKegg
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetateGenerator
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetateGenerator
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetateGenerator
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetateGenerator
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetateGenerator
ETODOLateGenerator
Etodolac, (-)-isomerMeSH, HMDB
Etodolac, monosodium saltMeSH, HMDB
Etodolac, (+-)-isomerMeSH, HMDB
Etodolac, monosodium salt, (S)-isomerMeSH, HMDB
Etodolac, monosodium salt, (+-) isomerMeSH, HMDB
UltradolMeSH, HMDB
Acid, etodolicMeSH, HMDB
Etodolac, (S)-isomerMeSH, HMDB
RamodarMeSH, HMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.3535
Monoisotopic Molecular Weight287.152143543
IUPAC Name2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
Traditional Nameetodolac
CAS Registry Number41340-25-4
SMILES
CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C1
InChI Identifier
InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
InChI KeyNNYBQONXHNTVIJ-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
  • Indole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 - 148 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.039 g/LNot Available
LogP2.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available164.408http://allccs.zhulab.cn/database/detail?ID=AllCCS00001013
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.39ALOGPS
logP3.44ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.16 m³·mol⁻¹ChemAxon
Polarizability31.94 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]+167.84731661259
DarkChem[M-H]-167.77531661259
DeepCCS[M+H]+170.77130932474
DeepCCS[M-H]-168.41330932474
DeepCCS[M-2H]-201.29930932474
DeepCCS[M+Na]+176.86430932474
AllCCS[M+H]+168.532859911
AllCCS[M+H-H2O]+165.032859911
AllCCS[M+NH4]+171.732859911
AllCCS[M+Na]+172.732859911
AllCCS[M-H]-175.132859911
AllCCS[M+Na-2H]-175.032859911
AllCCS[M+HCOO]-175.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EtodolacCCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C13691.6Standard polar33892256
EtodolacCCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C12323.4Standard non polar33892256
EtodolacCCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C12499.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Etodolac,1TMS,isomer #1CCC1=CC=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2508.6Semi standard non polar33892256
Etodolac,1TMS,isomer #2CCC1=CC=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O2594.3Semi standard non polar33892256
Etodolac,2TMS,isomer #1CCC1=CC=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2567.5Semi standard non polar33892256
Etodolac,2TMS,isomer #1CCC1=CC=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2439.0Standard non polar33892256
Etodolac,2TMS,isomer #1CCC1=CC=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C2757.9Standard polar33892256
Etodolac,1TBDMS,isomer #1CCC1=CC=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C2749.1Semi standard non polar33892256
Etodolac,1TBDMS,isomer #2CCC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O2778.7Semi standard non polar33892256
Etodolac,2TBDMS,isomer #1CCC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C2947.4Semi standard non polar33892256
Etodolac,2TBDMS,isomer #1CCC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C2883.8Standard non polar33892256
Etodolac,2TBDMS,isomer #1CCC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C2949.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-5690000000-7138dacb1eaaf2cdf09b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9178000000-933928ecb8877343883c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etodolac GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-qTof , Positive-QTOFsplash10-0002-3962000000-2dfafa7266e72ac813b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , negative-QTOFsplash10-000l-0090000000-cb5392bab35da402835e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , negative-QTOFsplash10-0006-0090000000-66382e8a032519cc06102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , negative-QTOFsplash10-03di-0090000000-1ab9e4ff7d60e90eca2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , negative-QTOFsplash10-03di-0290000000-308131d28773ab2c97012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , negative-QTOFsplash10-03dj-0890000000-ba74bd4789a5df9d10952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , negative-QTOFsplash10-01pk-0920000000-3003d9d94ce99518b55e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QQ , negative-QTOFsplash10-000i-0090000000-1644ab62d0cb24cc769e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QQ , negative-QTOFsplash10-000f-0090000000-0d0a55600dd433d684b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QQ , negative-QTOFsplash10-01ox-0090000000-17b2c48a871d73f3071a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QQ , negative-QTOFsplash10-03di-0290000000-fe771b5ef7a99c3f79dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QQ , negative-QTOFsplash10-03dj-0980000000-50aec638935d673b713e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , positive-QTOFsplash10-00di-0910000000-ca92c4a042f65a5a6c9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , positive-QTOFsplash10-00di-0920000000-22f891e69de842afb76f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , positive-QTOFsplash10-00di-0910000000-3903a65f3f64f26aa9b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , positive-QTOFsplash10-006x-0900000000-5bb09419198c9ca084c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , positive-QTOFsplash10-0006-0900000000-61c0ea8a828fd0570b072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QFT , positive-QTOFsplash10-0006-0900000000-4bec68aee4ff03d6d3862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Etodolac LC-ESI-QQ , positive-QTOFsplash10-00dr-0890000000-e286df97fed2602fd7592017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etodolac 10V, Positive-QTOFsplash10-0079-0090000000-39c676afa45ed8a7e0182016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etodolac 20V, Positive-QTOFsplash10-009f-0490000000-51e44ee3189b0f50c1732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etodolac 40V, Positive-QTOFsplash10-0006-1900000000-6dd7415f505d8fdf07962016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etodolac 10V, Negative-QTOFsplash10-000f-0090000000-8e401f59407e86d7026a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etodolac 20V, Negative-QTOFsplash10-01tl-0090000000-76de8abd58830a4798de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etodolac 40V, Negative-QTOFsplash10-0r03-0950000000-379fd5765e047bf96bfb2016-08-03Wishart 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 DB00749 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00749 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 ID3192
KEGG Compound IDC06991
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtodolac
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID4909
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