Record Information
Version1.0
Creation date2011-09-21 00:20:25 UTC
Update date2015-07-21 06:57:23 UTC
Primary IDFDB022841
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsovalerylglucuronide
DescriptionIsovaleryl glucuronide has been identified in the urine of patients with isovaleric acidemia made possible by using gas chromatograph-mass spectrometry (GC-MS). Isovaleryl glucuronide is more likely to be excreted when the amount of urinary 3-hydroxyisovaleric acid excretion is high. Isovaleryl glucuronide is more likely to be excreted when the amount of urinary 3-hydroxyisovaleric acid excretion is high. (PMID: 6547525) Isovaleric academia is caused by mutation in the isovaleryl CoA dehydrogenase gene and is closely related to maple syrup urine disease. It presents in two forms: the acute neonatal form, leading to massive metabolic acidosis from the first days of life and rapid death and a chronic form in which periodic attacks of severe ketoacidosis occur with asymptomatic intervening periods. (OMIM 243500) [HMDB]
CAS Number88070-93-3
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility65.8 g/LALOGPS
logP-0.98ALOGPS
logP-0.74ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.72 m³·mol⁻¹ChemAxon
Polarizability25.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H18O8
IUPAC name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(3-methylbutanoyl)oxy]oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C11H18O8/c1-4(2)3-5(12)18-11-8(15)6(13)7(14)9(19-11)10(16)17/h4,6-9,11,13-15H,3H2,1-2H3,(H,16,17)/t6-,7-,8+,9-,11+/m0/s1
InChI KeyVOJAALAAOYUSCT-ZCLKDUABSA-N
Isomeric SMILESCC(C)CC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
Average Molecular Weight278.2558
Monoisotopic Molecular Weight278.100167552
Classification
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
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Fatty acyl
  • Oxane
  • Pyran
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Polyol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsovalerylglucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bti-9220000000-6e98f010cd0467b072dcSpectrum
Predicted GC-MSIsovalerylglucuronide, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-9211530000-ed8a112c3ce8a22c41abSpectrum
Predicted GC-MSIsovalerylglucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9530000000-9ab66c3cef3bb9fae9d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-6910000000-35cc942e2f34ec6c85e62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kal-9500000000-8a10e23ebdbc62d764402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4490000000-513a7a09db01fdc791b62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-8910000000-555c1a494191dce249092021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pwc-9100000000-4a4fed85a07fc84734682021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f9i-7950000000-fb152377058310592d462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9f-9400000000-964d15690557099e95662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9300000000-be3f4689594e707c27aa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-d451737097d2392c8bb62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9400000000-44f04e96b887fd4a753e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9300000000-546f807e53b36a703d862021-09-24View Spectrum
NMRNot Available
ChemSpider ID121058
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID137383
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02091
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
AnatidaeExpected but not quantifiedNot AvailableHMDB
BeefaloExpected but not quantifiedNot AvailableHMDB
BisonExpected but not quantifiedNot AvailableHMDB
BuffaloExpected but not quantifiedNot AvailableHMDB
Cattle (Beef, Veal)Expected but not quantifiedNot AvailableHMDB
ChickenExpected but not quantifiedNot AvailableHMDB
Columbidae (Dove, Pigeon)Expected but not quantifiedNot AvailableHMDB
DeerExpected but not quantifiedNot AvailableHMDB
Domestic goatExpected but not quantifiedNot AvailableHMDB
Domestic pigExpected but not quantifiedNot AvailableHMDB
Showing 1 to 10 of 29 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference