Valproic acid glucuronide (CHEM022504)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:37:47 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022504
Identification
Common NameValproic acid glucuronide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Valproate glucuronideGenerator
1-(2-PropylpentanoateHMDB
1-(2-Propylpentanoate) beta-D-glucopyranuronateHMDB
1-(2-Propylpentanoate) beta-D-glucopyranuronic acidHMDB
1-(2-Propylpentanoate) beta-delta-glucopyranuronateHMDB
1-(2-Propylpentanoate) beta-delta-glucopyranuronic acidHMDB
1-(2-Propylpentanoic acidHMDB
1-O-Valproyl-b-D-glucopyranuronic acidHMDB
1-O-Valproyl-beta-delta-glucopyranuronic acidHMDB
3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylateHMDB
3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acidHMDB
Dipropylacetate glucuronideHMDB
MyproateHMDB
Myproic acidHMDB
ValproateHMDB
Valproic acidHMDB
VPA-gHMDB
VPAGHMDB
Chemical FormulaC14H24O8
Average Molecular Mass320.336 g/mol
Monoisotopic Mass320.147 g/mol
CAS Registry Number60113-83-9
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
SMILESCCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1
InChI KeyXXKSYIHWRBBHIC-JVWRJRKNSA-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
  • 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
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 Solubility22.2 g/LALOGPS
logP0.2ALOGPS
logP0.85ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.55 m³·mol⁻¹ChemAxon
Polarizability32.52 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pds-9221000000-c4a088ea62b38f27162dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0006-7101290000-cfd964bab66e1a7f52c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0902000000-2aede4223010fbfa28cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-4900000000-8d4033ca0760506b6c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002e-9700000000-9b150785b1449fefe60eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mo-2913000000-c1208d610d940b866f24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-4910000000-881718af4775dafc78f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9700000000-2d69130ba045cf068e49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1209000000-1fe9a50772ce5d04154fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-9301000000-7e6b8c6eaca54df62353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9100000000-b293f27db4ba83db2396Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0109000000-980c74ef8113693a80e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mp-3901000000-192aebcbdfefe9b795c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9400000000-1078233b81443bce6776Spectrum
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 IDHMDB0000901
FooDB IDFDB022308
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2991
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID88111
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yamamura, Naotoshi; Muramatsu, Shigeki; Suzuki, Kanae; Uchiyama, Minoru; Nakajima, Eiichi. High-yield, enzymic synthesis of 14C- or 3H-labeled 1-O-valproyl-b-D-glucopyranuronic acid, the main metabolite of valproic acid in human. Radioisotopes (1999), 48(
2. Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46.
3. Bell EC, Willson MC, Wilman AH, Dave S, Silverstone PH: Differential effects of chronic lithium and valproate on brain activation in healthy volunteers. Hum Psychopharmacol. 2005 Aug;20(6):415-24.
4. Sztajnkrycer MD: Valproic acid toxicity: overview and management. J Toxicol Clin Toxicol. 2002;40(6):789-801.
5. Yoshida H, Hirozane K, Kimoto H, Hayashi T, Akiyama T, Katayama H, Watanabe M, Yoshitomi H, Kamiya A: Valproic acid elimination rate and urinary excretion of its glucuronide conjugate in patients with epilepsy. Biol Pharm Bull. 1999 Jul;22(7):716-20.
6. Seyfert S, Bernarding J, Braun J: Volume-selective 1H MR spectroscopy for in vivo detection of valproate in patients with epilepsy. Neuroradiology. 2003 May;45(5):295-9. Epub 2003 Mar 27.
7. Eyal S, Lamb JG, Smith-Yockman M, Yagen B, Fibach E, Altschuler Y, White HS, Bialer M: The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver. Br J Pharmacol. 2006 Oct;149(3):250-60. Epub 2006 Aug 7.
8. Bailey DN, Briggs JR: Valproic acid binding to human serum and human placenta in vitro. Ther Drug Monit. 2005 Jun;27(3):375-7.
9. Safford KM, Hicok KC, Safford SD, Halvorsen YD, Wilkison WO, Gimble JM, Rice HE: Neurogenic differentiation of murine and human adipose-derived stromal cells. Biochem Biophys Res Commun. 2002 Jun 7;294(2):371-9.
10. Queizan A, Hernandez F, Rivas S: Pancreatic pseudocyst caused by valproic acid: case report and review of the literature. Eur J Pediatr Surg. 2003 Feb;13(1):60-2.
11. Loscher W: Basic pharmacology of valproate: a review after 35 years of clinical use for the treatment of epilepsy. CNS Drugs. 2002;16(10):669-94.
12. Fowler DW, Eadie MJ, Dickinson RG: Transplacental transfer and biotransformation studies of valproic acid and its glucuronide(s) in the perfused human placenta. J Pharmacol Exp Ther. 1989 Apr;249(1):318-23.
13. Serdaroglu G, Erhan E, Tekgul H, Oksel F, Erermis S, Uyar M, Tutuncuoglu S: Sodium valproate prophylaxis in childhood migraine. Headache. 2002 Sep;42(8):819-22.
14. Kim JM, Jung KY, Choi CM: Changes in brain complexity during valproate treatment in patients with partial epilepsy. Neuropsychobiology. 2002;45(2):106-12.
15. Huang YL, Hong HS, Wang ZW, Kuo TT: Fatal sodium valproate-induced hypersensitivity syndrome with lichenoid dermatitis and fulminant hepatitis. J Am Acad Dermatol. 2003 Aug;49(2):316-9.
16. Dickinson RG, Kluck RM, Hooper WD, Patterson M, Chalk JB, Eadie MJ: Rearrangement of valproate glucuronide in a patient with drug-associated hepatobiliary and renal dysfunction. Epilepsia. 1985 Nov-Dec;26(6):589-93.
17. Williams AM, Worrall S, de Jersey J, Dickinson RG: Studies on the reactivity of acyl glucuronides--III. Glucuronide-derived adducts of valproic acid and plasma protein and anti-adduct antibodies in humans. Biochem Pharmacol. 1992 Feb 18;43(4):745-55.
18. Nakamura H, Ushigome F, Koyabu N, Satoh S, Tsukimori K, Nakano H, Ohtani H, Sawada Y: Proton gradient-dependent transport of valproic acid in human placental brush-border membrane vesicles. Pharm Res. 2002 Feb;19(2):154-61.
19. De Berardis D, Campanella D, Matera V, Gambi F, La Rovere R, Sepede G, Grimaldi MR, Pacilli AM, Salerno RM, Ferro FM: Thrombocytopenia during valproic acid treatment in young patients with new-onset bipolar disorder. J Clin Psychopharmacol. 2003 Oct;23(5):451-8.
20. Anderson GD, Temkin NR, Chandler WL, Winn HR: Effect of valproate on hemostatic function in patients with traumatic brain injury. Epilepsy Res. 2003 Dec;57(2-3):111-9.
21. Mallet L, Babin S, Morais JA: Valproic acid-induced hyperammonemia and thrombocytopenia in an elderly woman. Ann Pharmacother. 2004 Oct;38(10):1643-7. Epub 2004 Aug 17.
22. Gerstner T, Bell N, Konig S: Oral valproic acid for epilepsy--long-term experience in therapy and side effects. Expert Opin Pharmacother. 2008 Feb;9(2):285-92. doi: 10.1517/14656566.9.2.285 .
23. Russell S: Carnitine as an antidote for acute valproate toxicity in children. Curr Opin Pediatr. 2007 Apr;19(2):206-10.
24. Wong H, Tong V, Riggs KW, Rurak DW, Abbott FS, Kumar S: Kinetics of valproic acid glucuronidation: evidence for in vivo autoactivation. Drug Metab Dispos. 2007 Aug;35(8):1380-6. Epub 2007 May 11.