Mycophenolic acid O-acyl-glucuronide (CHEM022578)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:40:06 UTC
Update Date2016-11-09 01:17:32 UTC
Accession NumberCHEM022578
Identification
Common NameMycophenolic acid O-acyl-glucuronide
ClassSmall Molecule
DescriptionA carboxylic ester resulting from the formal condensation of the carboxylic acid group of mycophenolic acid with the anomeric hydroxy group of beta-D-glucuronic acid.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AcMPAGChEBI
Mycophenolic acid acyl glucuronideChEBI
Mycophenolic acid acyl-glucuronideChEBI
Mycophenolic acid-O-acyl-beta-D-glucopyranuronosideChEBI
Mycophenolate acyl glucuronideGenerator
Mycophenolate acyl-glucuronideGenerator
Mycophenolate-O-acyl-b-D-glucopyranuronosideGenerator
Mycophenolate-O-acyl-beta-D-glucopyranuronosideGenerator
Mycophenolate-O-acyl-β-D-glucopyranuronosideGenerator
Mycophenolic acid-O-acyl-b-D-glucopyranuronosideGenerator
Mycophenolic acid-O-acyl-β-D-glucopyranuronosideGenerator
Mycophenolate O-acyl-glucuronideGenerator
Chemical FormulaC23H28O12
Average Molecular Mass496.461 g/mol
Monoisotopic Mass496.158 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid
SMILESCOC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C23H28O12/c1-9(4-6-11-15(25)14-12(8-33-22(14)31)10(2)19(11)32-3)5-7-13(24)34-23-18(28)16(26)17(27)20(35-23)21(29)30/h4,16-18,20,23,25-28H,5-8H2,1-3H3,(H,29,30)/b9-4+/t16-,17-,18+,20-,23+/m0/s1
InChI KeyQBMSTEZXAMABFF-UEARNRKISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Isobenzofuranone
  • Phthalide
  • Isocoumaran
  • Tricarboxylic acid or derivatives
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty acyl
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP0.91ALOGPS
logP1.58ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.53 m³·mol⁻¹ChemAxon
Polarizability49.24 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9132400000-8d1d445b5c92387b8fddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9807007000-7f6173b63131c0199045Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Mycophenolic acid O-acyl-glucuronide,3TBDMS,#6" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1229400000-a00fd0b14652a8a073e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v00-3927200000-b03a15a97c3652e63eb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0miy-9725000000-7d44f74d3818db669d41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001900000-3a9bf5cebae751792deeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ktb-2054900000-3d6868acf21096f78353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-1192200000-4eb5e92df9f368cdbdd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi1-0539500000-bfc6fff89aeca9bc0aebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kk9-1898200000-2b4abbcf7a3d676e09ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3951000000-bf27b3a68a384eb61846Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0032900000-688e9215c56e8c6bc792Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0091000000-e2000425e22fefbd07adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0091100000-9d561f09ce0219cf3eaaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060491
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID64689
PubChem Compound ID10028772
Kegg Compound IDC20383
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16931568
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17908922
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19744471
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21839692
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22294686
6. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.