ContaminantDB: Protoanemonin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:58:55 UTC

Update Date

2026-05-20 22:33:18 UTC

Accession Number

CHEM003014

Identification

Common Name

Protoanemonin

Class

Small Molecule

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.

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Metabolite
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

96.084 g/mol

Monoisotopic Mass

96.021 g/mol

CAS Registry Number

108-28-1

IUPAC Name

Not Available

Traditional Name

protoanemonin

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9000000000-ef6687a610aaecacb239	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-b6ec422705a7e5123bd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-eb44835609142e75cd73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-48eb1e104da3a0781110	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-267c360d9734babaaf71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-9000000000-b5df9916b5d89d825827	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-9000000000-b10e731dcce77040411c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9000000000-0468df05f34781217bbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9000000000-2554939f5adee81a5d0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-7c59f5639a0b7186edf0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-53fba820360e0c7016f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-9000000000-584b27ea4de09075451c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9000000000-3d945f0594de6c0d8fc9	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0060503

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00000301

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Protoanemonin

Chemspider ID

Not Available

ChEBI ID

28906

PubChem Compound ID

66948

Kegg Compound ID

C07090

YMDB ID

Not Available

ECMDB ID

ECMDB20185

References

Synthesis Reference

Not Available

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.

Protoanemonin (CHEM003014)

Structure for CHEM003014: Protoanemonin