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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:55:45 UTC
Update Date2021-09-14 15:47:57 UTC
HMDB IDHMDB0042044
Secondary Accession Numbers
  • HMDB42044
Metabolite Identification
Common NameTolmetin glucuronide
DescriptionTolmetin glucuronide belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on Tolmetin glucuronide.
Structure
Data?1563863724
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylateHMDB
Tolmetin glucuronideMeSH
Chemical FormulaC21H23NO9
Average Molecular Weight433.4086
Monoisotopic Molecular Weight433.137281339
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylic acid
CAS Registry Number71595-19-2
SMILES
CN1C(CC(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C21H23NO9/c1-10-3-5-11(6-4-10)15(24)13-8-7-12(22(13)2)9-14(23)30-21-18(27)16(25)17(26)19(31-21)20(28)29/h3-8,16-19,21,25-27H,9H2,1-2H3,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
InChI KeyMEFIGCPEYJZFFC-ZFORQUDYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • Hippuric acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Carboxamide group
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Ether
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP0.8ALOGPS
logP0.78ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.12ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.69 m³·mol⁻¹ChemAxon
Polarizability43.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.06431661259
DarkChem[M-H]-200.97931661259
DeepCCS[M+H]+199.84730932474
DeepCCS[M-H]-198.02330932474
DeepCCS[M-2H]-231.26630932474
DeepCCS[M+Na]+205.45430932474
AllCCS[M+H]+204.632859911
AllCCS[M+H-H2O]+202.132859911
AllCCS[M+NH4]+206.932859911
AllCCS[M+Na]+207.632859911
AllCCS[M-H]-200.532859911
AllCCS[M+Na-2H]-201.332859911
AllCCS[M+HCOO]-202.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tolmetin glucuronideCN1C(CC(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C14498.7Standard polar33892256
Tolmetin glucuronideCN1C(CC(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C13167.0Standard non polar33892256
Tolmetin glucuronideCN1C(CC(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C13651.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tolmetin glucuronide,1TMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O)N2C)C=C13411.8Semi standard non polar33892256
Tolmetin glucuronide,1TMS,isomer #2CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)N2C)C=C13412.0Semi standard non polar33892256
Tolmetin glucuronide,1TMS,isomer #3CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)N2C)C=C13414.3Semi standard non polar33892256
Tolmetin glucuronide,1TMS,isomer #4CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)N2C)C=C13407.7Semi standard non polar33892256
Tolmetin glucuronide,2TMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O)N2C)C=C13427.1Semi standard non polar33892256
Tolmetin glucuronide,2TMS,isomer #2CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O)N2C)C=C13413.6Semi standard non polar33892256
Tolmetin glucuronide,2TMS,isomer #3CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C)N2C)C=C13422.2Semi standard non polar33892256
Tolmetin glucuronide,2TMS,isomer #4CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)N2C)C=C13407.6Semi standard non polar33892256
Tolmetin glucuronide,2TMS,isomer #5CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)N2C)C=C13405.9Semi standard non polar33892256
Tolmetin glucuronide,2TMS,isomer #6CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)N2C)C=C13410.4Semi standard non polar33892256
Tolmetin glucuronide,3TMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O)N2C)C=C13430.5Semi standard non polar33892256
Tolmetin glucuronide,3TMS,isomer #2CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C)N2C)C=C13450.4Semi standard non polar33892256
Tolmetin glucuronide,3TMS,isomer #3CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)N2C)C=C13441.7Semi standard non polar33892256
Tolmetin glucuronide,3TMS,isomer #4CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)N2C)C=C13427.7Semi standard non polar33892256
Tolmetin glucuronide,4TMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)N2C)C=C13471.8Semi standard non polar33892256
Tolmetin glucuronide,1TBDMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O)N2C)C=C13654.8Semi standard non polar33892256
Tolmetin glucuronide,1TBDMS,isomer #2CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)N2C)C=C13667.2Semi standard non polar33892256
Tolmetin glucuronide,1TBDMS,isomer #3CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C13665.8Semi standard non polar33892256
Tolmetin glucuronide,1TBDMS,isomer #4CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)N2C)C=C13666.0Semi standard non polar33892256
Tolmetin glucuronide,2TBDMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O)N2C)C=C13900.2Semi standard non polar33892256
Tolmetin glucuronide,2TBDMS,isomer #2CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)N2C)C=C13877.0Semi standard non polar33892256
Tolmetin glucuronide,2TBDMS,isomer #3CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C13885.9Semi standard non polar33892256
Tolmetin glucuronide,2TBDMS,isomer #4CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)N2C)C=C13894.3Semi standard non polar33892256
Tolmetin glucuronide,2TBDMS,isomer #5CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C13885.3Semi standard non polar33892256
Tolmetin glucuronide,2TBDMS,isomer #6CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C13901.4Semi standard non polar33892256
Tolmetin glucuronide,3TBDMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)N2C)C=C14079.0Semi standard non polar33892256
Tolmetin glucuronide,3TBDMS,isomer #2CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C14108.3Semi standard non polar33892256
Tolmetin glucuronide,3TBDMS,isomer #3CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C14067.4Semi standard non polar33892256
Tolmetin glucuronide,3TBDMS,isomer #4CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C14077.1Semi standard non polar33892256
Tolmetin glucuronide,4TBDMS,isomer #1CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)N2C)C=C14263.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tolmetin glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-9412100000-77dacc15b58f01cf72372017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolmetin glucuronide GC-MS (3 TMS) - 70eV, Positivesplash10-001u-7393047000-9d23f8385fbb263b4c272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolmetin glucuronide 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 - Tolmetin glucuronide 10V, Positive-QTOFsplash10-05mo-0490400000-f623cdbf93269347b53e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 20V, Positive-QTOFsplash10-066u-0980000000-ff8b6e6b1ae30fdcbd4c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 40V, Positive-QTOFsplash10-014r-2910000000-1f86c8da9417287e442c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 10V, Negative-QTOFsplash10-000i-1191200000-d037ea3e202cdb8ff50c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 20V, Negative-QTOFsplash10-0a73-3791100000-d934c3dc59294ee869992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 40V, Negative-QTOFsplash10-0a4u-8690000000-fa447f3a73feccb3f5512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 10V, Positive-QTOFsplash10-014i-0334900000-025c5b45742f5ab94afc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 20V, Positive-QTOFsplash10-014l-3794200000-8c2cce65aa69e93e4ec82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 40V, Positive-QTOFsplash10-0006-9631000000-cba1a21eb758d20d28ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 10V, Negative-QTOFsplash10-08gi-0190200000-8a768ee4f397e8c81e442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 20V, Negative-QTOFsplash10-03du-4390100000-19f9dfabad674d825a342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolmetin glucuronide 40V, Negative-QTOFsplash10-074u-9761100000-983c88ad870dfa0a88f22021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 ID137120
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155656
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