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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:06:16 UTC
Update Date2021-09-26 23:02:41 UTC
HMDB IDHMDB0250947
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydrocrotonin
Description5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydrocrotonin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrocrotonin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H22O4
Average Molecular Weight314.381
Monoisotopic Molecular Weight314.151809188
IUPAC Name5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione
Traditional Name5'-(furan-3-yl)-2,5-dimethyl-2,3,4,4a,8,8a-hexahydrospiro[naphthalene-1,3'-oxolane]-2',7-dione
CAS Registry NumberNot Available
SMILES
CC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C1
InChI Identifier
InChI=1S/C19H22O4/c1-11-7-14(20)8-16-15(11)4-3-12(2)19(16)9-17(23-18(19)21)13-5-6-22-10-13/h5-7,10,12,15-17H,3-4,8-9H2,1-2H3
InChI KeyPHTWCRQCDPNVLQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentDiterpene lactones
Alternative Parents
Substituents
  • Diterpene lactone
  • Diterpenoid
  • Clerodane diterpenoid
  • Cyclohexenone
  • Gamma butyrolactone
  • Heteroaromatic compound
  • Furan
  • Oxolane
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not 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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(2.96) g/LALOGPS
logP10(3.39) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)18.67ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area56.51 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.24 m³·mol⁻¹ChemAxon
Polarizability33.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydrocrotoninCC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C13745.1Standard polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
DehydrocrotoninCC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C12520.0Standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
DehydrocrotoninCC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C12780.4Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrocrotonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00gi-5960000000-db8b4ed51b5441dd17912021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrocrotonin 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 - Dehydrocrotonin 10V, Positive-QTOFsplash10-014i-0009000000-94c839719c28eb6a5bbf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrocrotonin 20V, Positive-QTOFsplash10-014i-0195000000-b308db89295ce2d618372021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrocrotonin 40V, Positive-QTOFsplash10-00ks-3980000000-b68e1fd9a9cda892741b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrocrotonin 10V, Negative-QTOFsplash10-03di-0009000000-39b39050eae413a9d5072021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrocrotonin 20V, Negative-QTOFsplash10-03di-2029000000-ddf5e41feec965d414a42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrocrotonin 40V, Negative-QTOFsplash10-029b-6942000000-4b482543d4f9cc53ae072021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14313505
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]