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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:25:30 UTC
Update Date2023-02-21 17:30:03 UTC
HMDB IDHMDB0060503
Secondary Accession Numbers
  • HMDB60503
Metabolite Identification
Common NameProtoanemonin
DescriptionProtoanemonin (sometimes called anemonol or ranunculol) is a toxin found in all plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is produced by an enzymatic process from the glucoside ranunculin. It is the lactone of 4-hydroxy-2,4-pentadienoic acid. A wounded plant releases the substance, causing itch, rashes or blistering on contact with the skin or mucosa. (Wikipedia )
Structure
Data?1677000603
Synonyms
ValueSource
4-Methylenebut-2-en-4-olideChEBI
5-Methylene-2(5H)-furanoneChEBI
cis-4-Methylenebut-2-en-4-olideChEBI
5-Methylene-2-furanoneHMDB
Chemical FormulaC5H4O2
Average Molecular Weight96.0841
Monoisotopic Molecular Weight96.021129372
IUPAC Name5-methylidene-2,5-dihydrofuran-2-one
Traditional Nameprotoanemonin
CAS Registry NumberNot Available
SMILES
C=C1OC(=O)C=C1
InChI Identifier
InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
InChI KeyRNYZJZKPGHQTJR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Enol ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility61.8 g/LALOGPS
logP0.7ALOGPS
logP0.76ChemAxon
logS-0.19ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.01 m³·mol⁻¹ChemAxon
Polarizability8.82 ųChemAxon
Number of Rings1ChemAxon
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]+119.23931661259
DarkChem[M-H]-112.87331661259
DeepCCS[M+H]+119.37630932474
DeepCCS[M-H]-116.32230932474
DeepCCS[M-2H]-153.1230932474
DeepCCS[M+Na]+127.94330932474
AllCCS[M+H]+118.332859911
AllCCS[M+H-H2O]+113.132859911
AllCCS[M+NH4]+123.132859911
AllCCS[M+Na]+124.532859911
AllCCS[M-H]-116.132859911
AllCCS[M+Na-2H]-119.132859911
AllCCS[M+HCOO]-122.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProtoanemoninC=C1OC(=O)C=C11559.6Standard polar33892256
ProtoanemoninC=C1OC(=O)C=C1837.6Standard non polar33892256
ProtoanemoninC=C1OC(=O)C=C1902.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Protoanemonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-ef6687a610aaecacb2392017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protoanemonin 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 - Protoanemonin 10V, Positive-QTOFsplash10-0002-9000000000-b6ec422705a7e5123bd42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 20V, Positive-QTOFsplash10-0002-9000000000-eb44835609142e75cd732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 40V, Positive-QTOFsplash10-0udi-9000000000-48eb1e104da3a07811102016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 10V, Negative-QTOFsplash10-0002-9000000000-267c360d9734babaaf712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 20V, Negative-QTOFsplash10-0f6t-9000000000-b5df9916b5d89d8258272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 40V, Negative-QTOFsplash10-0udj-9000000000-b10e731dcce77040411c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 10V, Positive-QTOFsplash10-014j-9000000000-0468df05f34781217bbe2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 20V, Positive-QTOFsplash10-0udi-9000000000-2554939f5adee81a5d0d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 40V, Positive-QTOFsplash10-0udi-9000000000-7c59f5639a0b7186edf02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 10V, Negative-QTOFsplash10-0002-9000000000-53fba820360e0c7016f32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 20V, Negative-QTOFsplash10-0udj-9000000000-584b27ea4de09075451c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protoanemonin 40V, Negative-QTOFsplash10-0007-9000000000-3d945f0594de6c0d8fc92021-10-12Wishart 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+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDC00000301
Chemspider IDNot Available
KEGG Compound IDC07090
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProtoanemonin
METLIN IDNot Available
PubChem Compound66948
PDB IDNot Available
ChEBI ID28906
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Cysteine hydrolase. Can convert the prodrug olmesartan medoxomil into its pharmacologically active metabolite olmerstatan, an angiotensin receptor blocker, in liver and intestine. May also activate beta-lactam antibiotics faropenem medoxomil and lenampicillin.
Gene Name:
CMBL
Uniprot ID:
Q96DG6
Molecular weight:
Not Available
Reactions
Protoanemonin + Water → cis-Acetylacrylatedetails