Bovine Metabolome Database: Showing metabocard for Valproic acid glucuronide (BMDB0000901)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:20 UTC

Update Date

2020-05-11 20:44:15 UTC

BMDB ID

BMDB0000901

Secondary Accession Numbers

BMDB00901

Metabolite Identification

Common Name

Valproic acid glucuronide

Description

Valproic acid glucuronide, also known as 1-(2-propylpentanoate or dipropylacetate glucuronide, 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. Valproic acid glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Valproate glucuronide	Generator
1-(2-Propylpentanoate	HMDB
1-(2-Propylpentanoate) beta-D-glucopyranuronate	HMDB
1-(2-Propylpentanoate) beta-D-glucopyranuronic acid	HMDB
1-(2-Propylpentanoate) beta-delta-glucopyranuronate	HMDB
1-(2-Propylpentanoate) beta-delta-glucopyranuronic acid	HMDB
1-(2-Propylpentanoic acid	HMDB
1-O-Valproyl-b-D-glucopyranuronic acid	HMDB
1-O-Valproyl-beta-delta-glucopyranuronic acid	HMDB
3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylate	HMDB
3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid	HMDB
Dipropylacetate glucuronide	HMDB
Myproate	HMDB
Myproic acid	HMDB
Valproate	HMDB
Valproic acid	HMDB
VPA-g	HMDB
VPAG	HMDB

Chemical Formula

C₁₄H₂₄O₈

Average Molecular Weight

320.3356

Monoisotopic Molecular Weight

320.147117744

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

CAS Registry Number

60113-83-9

SMILES

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

InChI Identifier

InChI=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 Key

XXKSYIHWRBBHIC-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.

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

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.2	ALOGPS
logP	0.85	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.41	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	8	ChemAxon
Refractivity	72.55 m³·mol⁻¹	ChemAxon
Polarizability	32.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pds-9221000000-c4a088ea62b38f27162d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0006-7101290000-cfd964bab66e1a7f52c7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0902000000-2aede4223010fbfa28cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-4900000000-8d4033ca0760506b6c4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002e-9700000000-9b150785b1449fefe60e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00mo-2913000000-c1208d610d940b866f24	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-4910000000-881718af4775dafc78f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9700000000-2d69130ba045cf068e49	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1209000000-1fe9a50772ce5d04154f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-9301000000-7e6b8c6eaca54df62353	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9100000000-b293f27db4ba83db2396	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0109000000-980c74ef8113693a80e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mp-3901000000-192aebcbdfefe9b795c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-9400000000-1078233b81443bce6776	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Brain
Kidney
Liver
Pancreas
Placenta
Platelet

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000901

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

2991

PubChem Compound

88111

PDB ID

Not Available

ChEBI ID

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(

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Valproic acid glucuronide (BMDB0000901)

Structure for BMDB0000901 (Valproic acid glucuronide)