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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:20 UTC
Update Date2021-10-13 06:23:21 UTC
HMDB IDHMDB0032352
Secondary Accession Numbers
  • HMDB32352
Metabolite Identification
Common Name3-Isopropenylpentanedioic acid
Description3-Isopropenylpentanedioic acid, also known as 3-(prop-1-en-2-yl)pentanedioate, 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. Based on a literature review a significant number of articles have been published on 3-Isopropenylpentanedioic acid.
Structure
Data?1563862253
Synonyms
ValueSource
3-IsopropenylpentanedioateGenerator
3-(Prop-1-en-2-yl)pentanedioateHMDB
Chemical FormulaC8H12O4
Average Molecular Weight172.1785
Monoisotopic Molecular Weight172.073558872
IUPAC Name3-(prop-1-en-2-yl)pentanedioic acid
Traditional Name3-(prop-1-en-2-yl)pentanedioic acid
CAS Registry Number6839-75-4
SMILES
CC(=C)C(CC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C8H12O4/c1-5(2)6(3-7(9)10)4-8(11)12/h6H,1,3-4H2,2H3,(H,9,10)(H,11,12)
InChI KeyPULOWZXUQOLRBK-UHFFFAOYSA-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
  • Dicarboxylic 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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point110.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point297.00 to 299.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility18680 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.683 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.9 g/LALOGPS
logP10(0.77) g/LALOGPS
logP10(0.72) g/LChemAxon
logS10(-0.96) g/LALOGPS
pKa (Strongest Acidic)4.07ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.61 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.63431661259
DarkChem[M-H]-133.97431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Isopropenylpentanedioic acidCC(=C)C(CC(O)=O)CC(O)=O2411.5Standard polar33892256
3-Isopropenylpentanedioic acidCC(=C)C(CC(O)=O)CC(O)=O1203.4Standard non polar33892256
3-Isopropenylpentanedioic acidCC(=C)C(CC(O)=O)CC(O)=O1473.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Isopropenylpentanedioic acid,1TMS,isomer #1C=C(C)C(CC(=O)O)CC(=O)O[Si](C)(C)C1451.3Semi standard non polar33892256
3-Isopropenylpentanedioic acid,2TMS,isomer #1C=C(C)C(CC(=O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C1511.3Semi standard non polar33892256
3-Isopropenylpentanedioic acid,1TBDMS,isomer #1C=C(C)C(CC(=O)O)CC(=O)O[Si](C)(C)C(C)(C)C1688.9Semi standard non polar33892256
3-Isopropenylpentanedioic acid,2TBDMS,isomer #1C=C(C)C(CC(=O)O[Si](C)(C)C(C)(C)C)CC(=O)O[Si](C)(C)C(C)(C)C1965.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Isopropenylpentanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-021e9c1fe5a9600b30352017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Isopropenylpentanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-007c-9210000000-6218a9e78fa1583126c42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Isopropenylpentanedioic 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 - 3-Isopropenylpentanedioic acid 10V, Positive-QTOFsplash10-05fr-0900000000-e1a7648f7bd8c8c2b3312016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Positive-QTOFsplash10-056r-2900000000-7164be95760ff90db70c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Positive-QTOFsplash10-014i-9300000000-c323e6d1541179932ffa2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 10V, Negative-QTOFsplash10-00di-0900000000-e18526971334b45ecc562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Negative-QTOFsplash10-00fr-2900000000-5083b402aeb2aa277d742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Negative-QTOFsplash10-0aor-9700000000-a1d42a96ca692b2f3e0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 10V, Positive-QTOFsplash10-0159-9400000000-f4cc8e907832d4b7b3572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Positive-QTOFsplash10-0159-9100000000-91b914165162d3bed9de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Positive-QTOFsplash10-014l-9000000000-7e2e81a5753ea28421c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 10V, Negative-QTOFsplash10-00gi-4900000000-ecbbdb9ec2185484ed0a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 20V, Negative-QTOFsplash10-0a6r-7900000000-168c875fe54d462e22632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropenylpentanedioic acid 40V, Negative-QTOFsplash10-052f-9000000000-ac504438a38b604920452021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB009649
KNApSAcK IDC00057499
Chemspider ID21105929
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71586903
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1593981
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.