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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:52:56 UTC

Update Date

2021-09-26 22:54:32 UTC

HMDB ID

HMDB0245833

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone

Description

3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone, also known as mutagen X or 3-DCHFO, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Based on a literature review a significant number of articles have been published on 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5h)-furanone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Mutagen X	HMDB
3-DCHFO	HMDB
MX Mutagen	HMDB

Chemical Formula

C₅H₃Cl₃O₃

Average Molecular Weight

217.43

Monoisotopic Molecular Weight

215.9147771

IUPAC Name

3-chloro-4-(dichloromethyl)-5-hydroxy-2,5-dihydrofuran-2-one

Traditional Name

mutagen X

CAS Registry Number

Not Available

SMILES

OC1OC(=O)C(Cl)=C1C(Cl)Cl

InChI Identifier

InChI=1S/C5H3Cl3O3/c6-2-1(3(7)8)4(9)11-5(2)10/h3-4,9H

InChI Key

WNTRMRXAGJOLCU-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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Vinyl chloride
Vinyl halide
Chloroalkene
Haloalkene
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:82299 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	1.19	ALOGPS
logP	1.55	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.23 m³·mol⁻¹	ChemAxon
Polarizability	16.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	139.685	30932474
DeepCCS	[M-H]-	136.783	30932474
DeepCCS	[M-2H]-	172.888	30932474
DeepCCS	[M+Na]+	148.426	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.8	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	135.1	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone	OC1OC(=O)C(Cl)=C1C(Cl)Cl	2612.2	Standard polar	33892256
3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone	OC1OC(=O)C(Cl)=C1C(Cl)Cl	1542.8	Standard non polar	33892256
3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone	OC1OC(=O)C(Cl)=C1C(Cl)Cl	1565.7	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 - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-7900000000-b53b24a1b401c43305f9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 10V, Positive-QTOF	splash10-01b9-1980000000-3243b4301368765d26d7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 20V, Positive-QTOF	splash10-014i-1390000000-2b41c2ec9a80d5a44ebb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 40V, Positive-QTOF	splash10-000x-2900000000-c750d872ac441bea2f65	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 10V, Negative-QTOF	splash10-03k9-1970000000-5a5bc82be3251bb7f9ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 20V, Negative-QTOF	splash10-014i-0910000000-f7211eaae43ec8f3f4b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 40V, Negative-QTOF	splash10-00fr-8900000000-69e8fe442b52f309abb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 10V, Positive-QTOF	splash10-014i-0090000000-197395245112c7822353	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 20V, Positive-QTOF	splash10-014i-1390000000-6e0df66920926332032e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 40V, Positive-QTOF	splash10-0006-2900000000-3e5d7c74a9948e31c2fb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 10V, Negative-QTOF	splash10-03di-0290000000-30ad6f46d095c110ace4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 20V, Negative-QTOF	splash10-03di-2490000000-9f6aeca0274fa258e48b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone 40V, Negative-QTOF	splash10-001u-9410000000-52c09a49ad9e594df280	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

Chemspider ID

48451

KEGG Compound ID

C19205

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mutagen X

METLIN ID

Not Available

PubChem Compound

53665

PDB ID

Not Available

ChEBI ID

Not Available

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

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 ]

Showing metabocard for 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (HMDB0245833)

MOL for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

3D MOL for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

3D SDF for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

3D-SDF for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

PDB for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

3D PDB for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

SMILES for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

INCHI for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

Structure for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

3D Structure for HMDB0245833 (3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra