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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:49:51 UTC
Update Date2023-02-21 17:30:10 UTC
HMDB IDHMDB0060682
Secondary Accession Numbers
  • HMDB60682
Metabolite Identification
Common Name2-Propyl-2,4-pentadienoic acid
Description2-Propyl-2,4-pentadienoic 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
Data?1677000610
Synonyms
ValueSource
2,4-Diene-vpaKegg
2-Propyl-2,4-pentadienoateGenerator
2-Propyl-2,4-pentadienoic acid, (e)-isomerHMDB
2-PPDAHMDB
2-Propyl-2,4-pentadienoic acid, (Z)-isomerHMDB
Chemical FormulaC8H12O2
Average Molecular Weight140.1797
Monoisotopic Molecular Weight140.083729628
IUPAC Name(2E)-2-propylpenta-2,4-dienoic acid
Traditional Name2,4-Diene-VPA
CAS Registry NumberNot Available
SMILES
CCC\C(=C/C=C)C(O)=O
InChI Identifier
InChI=1S/C8H12O2/c1-3-5-7(6-4-2)8(9)10/h3,5H,1,4,6H2,2H3,(H,9,10)/b7-5+
InChI KeyUUILWXIBBZVJDU-FNORWQNLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.49 g/LALOGPS
logP2.28ALOGPS
logP2.34ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.17 m³·mol⁻¹ChemAxon
Polarizability15.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.27331661259
DarkChem[M-H]-130.44431661259
DeepCCS[M+H]+132.64530932474
DeepCCS[M-H]-129.09230932474
DeepCCS[M-2H]-166.04430932474
DeepCCS[M+Na]+141.30930932474
AllCCS[M+H]+134.332859911
AllCCS[M+H-H2O]+130.132859911
AllCCS[M+NH4]+138.332859911
AllCCS[M+Na]+139.432859911
AllCCS[M-H]-131.432859911
AllCCS[M+Na-2H]-133.632859911
AllCCS[M+HCOO]-136.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Propyl-2,4-pentadienoic acidCCC\C(=C/C=C)C(O)=O2010.9Standard polar33892256
2-Propyl-2,4-pentadienoic acidCCC\C(=C/C=C)C(O)=O1097.1Standard non polar33892256
2-Propyl-2,4-pentadienoic acidCCC\C(=C/C=C)C(O)=O1150.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Propyl-2,4-pentadienoic acid,1TMS,isomer #1C=C/C=C(\CCC)C(=O)O[Si](C)(C)C1225.5Semi standard non polar33892256
2-Propyl-2,4-pentadienoic acid,1TBDMS,isomer #1C=C/C=C(\CCC)C(=O)O[Si](C)(C)C(C)(C)C1454.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propyl-2,4-pentadienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-9200000000-ba4b7f259ad38315a5a92017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propyl-2,4-pentadienoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9400000000-403c0fc9bd59b1f80fde2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propyl-2,4-pentadienoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propyl-2,4-pentadienoic acid 10V, Positive-QTOFsplash10-0006-3900000000-6b67a18198af2bba243a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propyl-2,4-pentadienoic acid 20V, Positive-QTOFsplash10-0005-9400000000-29e2cfdc9d5d9eb176492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propyl-2,4-pentadienoic acid 40V, Positive-QTOFsplash10-0006-9000000000-ca5450d8710a12cb33d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propyl-2,4-pentadienoic acid 10V, Negative-QTOFsplash10-000i-4900000000-cc2ed0a2469c54811a582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propyl-2,4-pentadienoic acid 20V, Negative-QTOFsplash10-000b-9400000000-1d0218608b5da33ce9252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propyl-2,4-pentadienoic acid 40V, Negative-QTOFsplash10-000e-9100000000-eab2077c8aa959ce7bcb2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16656
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6441809
PDB IDNot Available
ChEBI ID80642
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.