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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:49:58 UTC

Update Date

2023-02-21 17:30:10 UTC

HMDB ID

HMDB0060684

Secondary Accession Numbers

HMDB60684

Metabolite Identification

Common Name

2-Propylglutaric acid

Description

2-Propylglutaric acid is a metabolite of valproic acid. Valproic acid (VPA) is a chemical compound and an acid that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy, bipolar disorder, and, less commonly, major depression. It is also used to treat migraine headaches and schizophrenia. VPA is a liquid at room temperature, but it can be reacted with a base such as sodium hydroxide to form the salt sodium valproate, which is a solid. (Wikipedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      28.055 -22.144   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.055 -20.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.727 -22.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.378 -22.933   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.720 -19.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.398 -22.144   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.378 -24.467   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      30.706 -22.144   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      25.392 -20.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.076 -22.933   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.732 -22.184   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.099 -24.465   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-PGA	Kegg
2-Propylglutarate	Generator

Chemical Formula

C₈H₁₄O₄

Average Molecular Weight

174.1944

Monoisotopic Molecular Weight

174.089208936

IUPAC Name

2-propylpentanedioic acid

Traditional Name

2-propylglutaric acid

CAS Registry Number

Not Available

SMILES

CCCC(CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H14O4/c1-2-3-6(8(11)12)4-5-7(9)10/h6H,2-5H2,1H3,(H,9,10)(H,11,12)

InChI Key

IFNXFIJXYVEYLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:80644 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060684)

Organ

Liver (HMDB: HMDB0060684)
Kidney (HMDB: HMDB0060684)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060684)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.99 g/L	ALOGPS
logP	0.83	ALOGPS
logP	1.48	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	41.91 m³·mol⁻¹	ChemAxon
Polarizability	17.99 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.703	31661259
DarkChem	[M-H]-	137.234	31661259
DeepCCS	[M+H]+	137.89	30932474
DeepCCS	[M-H]-	134.033	30932474
DeepCCS	[M-2H]-	171.69	30932474
DeepCCS	[M+Na]+	146.97	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.7	32859911
AllCCS	[M+NH4]+	145.2	32859911
AllCCS	[M+Na]+	146.2	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	142.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propylglutaric acid	CCCC(CCC(O)=O)C(O)=O	2424.3	Standard polar	33892256
2-Propylglutaric acid	CCCC(CCC(O)=O)C(O)=O	1260.1	Standard non polar	33892256
2-Propylglutaric acid	CCCC(CCC(O)=O)C(O)=O	1468.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Propylglutaric acid,1TMS,isomer #1	CCCC(CCC(=O)O[Si](C)(C)C)C(=O)O	1519.0	Semi standard non polar	33892256
2-Propylglutaric acid,1TMS,isomer #2	CCCC(CCC(=O)O)C(=O)O[Si](C)(C)C	1497.0	Semi standard non polar	33892256
2-Propylglutaric acid,2TMS,isomer #1	CCCC(CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1566.3	Semi standard non polar	33892256
2-Propylglutaric acid,1TBDMS,isomer #1	CCCC(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1759.1	Semi standard non polar	33892256
2-Propylglutaric acid,1TBDMS,isomer #2	CCCC(CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1733.0	Semi standard non polar	33892256
2-Propylglutaric acid,2TBDMS,isomer #1	CCCC(CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2011.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propylglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9700000000-107480ae32cb5322d6af	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propylglutaric acid GC-MS (2 TMS) - 70eV, Positive	splash10-0fg9-9231000000-3d69111ac7155080d324	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propylglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propylglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 10V, Positive-QTOF	splash10-0a6r-0900000000-4b6ab5c323c5a2872ff1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 20V, Positive-QTOF	splash10-0a6u-6900000000-97503f93698566c21d37	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 40V, Positive-QTOF	splash10-00lf-9000000000-dca7d555b3ca4e539126	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 10V, Negative-QTOF	splash10-00di-0900000000-711d6e6542c2093869a8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 20V, Negative-QTOF	splash10-0729-2900000000-ac692887907ca4a2fa18	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 40V, Negative-QTOF	splash10-0a4l-9300000000-9919e57cc5460399b31a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 10V, Negative-QTOF	splash10-00b9-0900000000-3e3ec55a970214330778	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 20V, Negative-QTOF	splash10-03fr-3900000000-5bca211482b7f7b76c93	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 40V, Negative-QTOF	splash10-0006-9300000000-b985293d8382f29425af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 10V, Positive-QTOF	splash10-057i-3900000000-1bb4dcf882f4c06bb706	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 20V, Positive-QTOF	splash10-067i-9100000000-526ac976f3c5a094a2b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propylglutaric acid 40V, Positive-QTOF	splash10-0a4l-9000000000-c72c58f981d9dc3f3812	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Valproic Acid Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16658

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134970

PDB ID

Not Available

ChEBI ID

80644

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-Propylglutaric acid (HMDB0060684)

MOL for HMDB0060684 (2-Propylglutaric acid)

3D MOL for HMDB0060684 (2-Propylglutaric acid)

3D SDF for HMDB0060684 (2-Propylglutaric acid)

3D-SDF for HMDB0060684 (2-Propylglutaric acid)

PDB for HMDB0060684 (2-Propylglutaric acid)

3D PDB for HMDB0060684 (2-Propylglutaric acid)

SMILES for HMDB0060684 (2-Propylglutaric acid)

INCHI for HMDB0060684 (2-Propylglutaric acid)

Structure for HMDB0060684 (2-Propylglutaric acid)

3D Structure for HMDB0060684 (2-Propylglutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra