ChemFOnt: Showing chemical card for Valproic acid glucuronide (CFc000000720)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:12 UTC

Chemfont ID

CFc000000720

Molecule Identification

Common Name

Valproic acid glucuronide

Definition

Valproic acid glucuronide is the glucuronidation product of valproic acid. Valproic acid, or 2-Propylpentanoic acid, is a chemical compound that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy and bipolar disorder, but also used to treat migraine headaches and schizophrenia. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures associated with Lennox-Gastaut syndrome. Glucuronidation is a vital phase 2 metabolic (conjugative) process by which a wide range of drugs and other xenobiotics may be rendered water-soluble, detoxified and excreted. Acyl (ester) glucuronides (AGs) of carboxylic acids are potentially reactive metabolites. In particular, AGs are important phase 2 metabolites for a wide range of carboxylic acid-containing drugs. (PMID: 18201150 , 17496767 , 17496206 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Valproate glucuronide	Generator

Chemical Formula

C₁₄H₂₄O₈

Average Molecular Weight

320.3356

Monoisotopic Molecular Weight

320.147117744

IUPAC Name

(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[2-(propan-2-yl)pentanoyl]oxy}oxane-2-carboxylic acid

Traditional Name

valproic acid glucuronide

CAS Registry Number

60113-83-9

SMILES

[H]C(CCC)(C(C)C)C(=O)OC1([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C14H24O8/c1-4-5-7(6(2)3)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h6-11,14-17H,4-5H2,1-3H3,(H,18,19)/t7?,8-,9-,10+,11-,14?/m0/s1

InChI Key

HFJIBPMXGQVSGX-HGIFLAPPSA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Adipose tissue (HMDB: HMDB0000901)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000901)

Organ

Cell

Hematocyte

Platelet (HMDB: HMDB0000901)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000901)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0000901)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	29.1 g/L	ALOGPS
logP	0.06	ALOGPS
logP	0.69	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.5 m³·mol⁻¹	ChemAxon
Polarizability	32.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022308

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477719

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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(

Showing chemical card for Valproic acid glucuronide (CFc000000720)

MOL for CFc000000720 (Valproic acid glucuronide)

3D MOL for CFc000000720 (Valproic acid glucuronide)

3D SDF for CFc000000720 (Valproic acid glucuronide)

3D-SDF for CFc000000720 (Valproic acid glucuronide)

PDB for CFc000000720 (Valproic acid glucuronide)

3D PDB for CFc000000720 (Valproic acid glucuronide)

SMILES for CFc000000720 (Valproic acid glucuronide)

INCHI for CFc000000720 (Valproic acid glucuronide)

Structure for CFc000000720 (Valproic acid glucuronide)

3D Structure for CFc000000720 (Valproic acid glucuronide)