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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:25:30 UTC

Update Date

2023-02-21 17:30:03 UTC

HMDB ID

HMDB0060503

Secondary Accession Numbers

HMDB60503

Metabolite Identification

Common Name

Protoanemonin

Description

Protoanemonin (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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Methylenebut-2-en-4-olide	ChEBI
5-Methylene-2(5H)-furanone	ChEBI
cis-4-Methylenebut-2-en-4-olide	ChEBI
5-Methylene-2-furanone	HMDB

Chemical Formula

C₅H₄O₂

Average Molecular Weight

96.0841

Monoisotopic Molecular Weight

96.021129372

IUPAC Name

5-methylidene-2,5-dihydrofuran-2-one

Traditional Name

protoanemonin

CAS Registry Number

Not Available

SMILES

C=C1OC(=O)C=C1

InChI Identifier

InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2

InChI Key

RNYZJZKPGHQTJR-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:28906 )
Phytotoxins (C07090 )
a small molecule (CPD-10640 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0060503)
Extracellular (HMDB: HMDB0060503)

Process

Not Available

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	61.8 g/L	ALOGPS
logP	0.7	ALOGPS
logP	0.76	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.01 m³·mol⁻¹	ChemAxon
Polarizability	8.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	119.239	31661259
DarkChem	[M-H]-	112.873	31661259
DeepCCS	[M+H]+	119.376	30932474
DeepCCS	[M-H]-	116.322	30932474
DeepCCS	[M-2H]-	153.12	30932474
DeepCCS	[M+Na]+	127.943	30932474
AllCCS	[M+H]+	118.3	32859911
AllCCS	[M+H-H2O]+	113.1	32859911
AllCCS	[M+NH4]+	123.1	32859911
AllCCS	[M+Na]+	124.5	32859911
AllCCS	[M-H]-	116.1	32859911
AllCCS	[M+Na-2H]-	119.1	32859911
AllCCS	[M+HCOO]-	122.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protoanemonin	C=C1OC(=O)C=C1	1559.6	Standard polar	33892256
Protoanemonin	C=C1OC(=O)C=C1	837.6	Standard non polar	33892256
Protoanemonin	C=C1OC(=O)C=C1	902.2	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 - Protoanemonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9000000000-ef6687a610aaecacb239	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoanemonin 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 - Protoanemonin 10V, Positive-QTOF	splash10-0002-9000000000-b6ec422705a7e5123bd4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 20V, Positive-QTOF	splash10-0002-9000000000-eb44835609142e75cd73	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 40V, Positive-QTOF	splash10-0udi-9000000000-48eb1e104da3a0781110	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 10V, Negative-QTOF	splash10-0002-9000000000-267c360d9734babaaf71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 20V, Negative-QTOF	splash10-0f6t-9000000000-b5df9916b5d89d825827	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 40V, Negative-QTOF	splash10-0udj-9000000000-b10e731dcce77040411c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 10V, Positive-QTOF	splash10-014j-9000000000-0468df05f34781217bbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 20V, Positive-QTOF	splash10-0udi-9000000000-2554939f5adee81a5d0d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 40V, Positive-QTOF	splash10-0udi-9000000000-7c59f5639a0b7186edf0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 10V, Negative-QTOF	splash10-0002-9000000000-53fba820360e0c7016f3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 20V, Negative-QTOF	splash10-0udj-9000000000-584b27ea4de09075451c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protoanemonin 40V, Negative-QTOF	splash10-0007-9000000000-3d945f0594de6c0d8fc9	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

C00000301

Chemspider ID

Not Available

KEGG Compound ID

C07090

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Protoanemonin

METLIN ID

Not Available

PubChem Compound

66948

PDB ID

Not Available

ChEBI ID

28906

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

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

Enzyme Details

1. Carboxymethylenebutenolidase homolog

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-Acetylacrylate	details

Showing metabocard for Protoanemonin (HMDB0060503)

MOL for HMDB0060503 (Protoanemonin)

3D MOL for HMDB0060503 (Protoanemonin)

3D SDF for HMDB0060503 (Protoanemonin)

3D-SDF for HMDB0060503 (Protoanemonin)

PDB for HMDB0060503 (Protoanemonin)

3D PDB for HMDB0060503 (Protoanemonin)

SMILES for HMDB0060503 (Protoanemonin)

INCHI for HMDB0060503 (Protoanemonin)

Structure for HMDB0060503 (Protoanemonin)

3D Structure for HMDB0060503 (Protoanemonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions