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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:59:27 UTC
Update Date2019-07-23 07:15:06 UTC
HMDB IDHMDB0060788
Secondary Accession Numbers
  • HMDB60788
Metabolite Identification
Common Name6-O-Desmethyl-mycophenolic acid
Description6-O-Desmethyl-mycophenolic acid belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 6-O-Desmethyl-mycophenolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-O-Desmethyl-mycophenolic acid is a metabolite of mycophenolic acid. It inhibits an enzyme needed for the growth of T cells and B cells. 6-O-desmethyl-mycophenolic acid and formaldehyde can be biosynthesized from mycophenolic acid; which is catalyzed by the enzymes cytochrome P450 3A4, cytochrome P450 3A5, and cytochrome P450 2C8. In humans, 6-O-desmethyl-mycophenolic acid is involved in mycophenolic acid metabolism pathway. It was initially marketed as the prodrug mycophenolate mofetil (MMF) to improve oral bioavailability. Mycophenolic acid or mycophenolate is an immunosuppressant drug used to prevent rejection in organ transplantation. Mycophenolic acid is commonly marketed under the trade names CellCept and Myfortic. More recently, the salt mycophenolate sodium has also been introduced.
Structure
Data?1563866105
Synonyms
ValueSource
6-O-Desmethyl-mycophenolateGenerator
Chemical FormulaC16H18O6
Average Molecular Weight306.3105
Monoisotopic Molecular Weight306.110338308
IUPAC Name6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
Traditional Name6-(4,6-dihydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
CAS Registry NumberNot Available
SMILES
CC(CCC(O)=O)=CCC1=C(O)C(C)=C2COC(=O)C2=C1O
InChI Identifier
InChI=1S/C16H18O6/c1-8(4-6-12(17)18)3-5-10-14(19)9(2)11-7-22-16(21)13(11)15(10)20/h3,19-20H,4-7H2,1-2H3,(H,17,18)
InChI KeyMHSRNZSBNXFMLF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Isobenzofuranone
  • Phthalide
  • Isocoumaran
  • Medium-chain fatty acid
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Unsaturated fatty acid
  • Fatty acid
  • Vinylogous acid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
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 Solubility0.084 g/LALOGPS
logP2.1ALOGPS
logP3.38ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.75 m³·mol⁻¹ChemAxon
Polarizability31.38 ųChemAxon
Number of Rings2ChemAxon
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]+172.1531661259
DarkChem[M-H]-169.93831661259
DeepCCS[M+H]+168.37930932474
DeepCCS[M-H]-166.02230932474
DeepCCS[M-2H]-199.46430932474
DeepCCS[M+Na]+174.69130932474
AllCCS[M+H]+171.232859911
AllCCS[M+H-H2O]+167.932859911
AllCCS[M+NH4]+174.232859911
AllCCS[M+Na]+175.132859911
AllCCS[M-H]-173.932859911
AllCCS[M+Na-2H]-173.832859911
AllCCS[M+HCOO]-173.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-O-Desmethyl-mycophenolic acidCC(CCC(O)=O)=CCC1=C(O)C(C)=C2COC(=O)C2=C1O4371.5Standard polar33892256
6-O-Desmethyl-mycophenolic acidCC(CCC(O)=O)=CCC1=C(O)C(C)=C2COC(=O)C2=C1O2631.5Standard non polar33892256
6-O-Desmethyl-mycophenolic acidCC(CCC(O)=O)=CCC1=C(O)C(C)=C2COC(=O)C2=C1O2858.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-O-Desmethyl-mycophenolic acid,1TMS,isomer #1CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O)CCC(=O)O[Si](C)(C)C2600.8Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,1TMS,isomer #2CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C)CCC(=O)O2664.1Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,1TMS,isomer #3CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O2660.4Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,2TMS,isomer #1CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C)CCC(=O)O[Si](C)(C)C2668.7Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,2TMS,isomer #2CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O[Si](C)(C)C2657.4Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,2TMS,isomer #3CC(=CCC1=C(O[Si](C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O2718.2Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,3TMS,isomer #1CC(=CCC1=C(O[Si](C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O[Si](C)(C)C2737.0Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,1TBDMS,isomer #1CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O)CCC(=O)O[Si](C)(C)C(C)(C)C2818.2Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,1TBDMS,isomer #2CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O2876.3Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,1TBDMS,isomer #3CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O2884.8Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,2TBDMS,isomer #1CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O[Si](C)(C)C(C)(C)C3110.7Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,2TBDMS,isomer #2CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O[Si](C)(C)C(C)(C)C3104.4Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,2TBDMS,isomer #3CC(=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O3168.3Semi standard non polar33892256
6-O-Desmethyl-mycophenolic acid,3TBDMS,isomer #1CC(=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O[Si](C)(C)C(C)(C)C3428.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-1190000000-c0f5cb5448f716834ad32017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-4104790000-88b6dd1b7b4c2071e6882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid 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-O-Desmethyl-mycophenolic acid 10V, Positive-QTOFsplash10-000i-0092000000-b9194ed275a421a8a7962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Positive-QTOFsplash10-03du-3490000000-1055c38862b60e2a54432017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Positive-QTOFsplash10-0gb9-9730000000-4a3915b3ffac607615da2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 10V, Negative-QTOFsplash10-0a4i-0069000000-e65af122fdd879e1678b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Negative-QTOFsplash10-0a4r-1093000000-51d47e208eeac0ebf63b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Negative-QTOFsplash10-0a4i-6390000000-964847eb7414adae072c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 10V, Positive-QTOFsplash10-0a4m-0987000000-770c963837f490cc31b82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Positive-QTOFsplash10-052f-2970000000-12469430d1cdcd28a9db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Positive-QTOFsplash10-0kbr-1910000000-7e35599874d5a204bc4b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 10V, Negative-QTOFsplash10-0a4i-0009000000-a4e78f227e456dc4b2b02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Negative-QTOFsplash10-0r29-1296000000-d3c43e0a118b2a36d3972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Negative-QTOFsplash10-014m-9660000000-a251ab7239f20c6b7c702021-10-12Wishart 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 Compound57369640
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