Jump To Section:

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 23:36:35 UTC

Update Date

2021-09-26 22:55:46 UTC

HMDB ID

HMDB0246593

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Vinylcyclohexene dioxide

Description

4-vinylcyclohexene dioxide belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Based on a literature review a small amount of articles have been published on 4-vinylcyclohexene dioxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-vinylcyclohexene dioxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Vinylcyclohexene dioxide 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
1-Epoxyethyl-3,4-epoxycyclohexane	ChEBI
1-Ethyleneoxy-3,4-epoxycyclohexane	ChEBI
1-Vinyl-3-cyclohexene dioxide	ChEBI
3-(1,2-Epoxyethyl)-7-oxabicyclo(4.1.0)heptane	ChEBI
3-(Epoxyethyl)-7-oxabicyclo(4.1.0)heptane	ChEBI
3-Oxiranyl-7-oxabicyclo(4.1.0)heptane	ChEBI
4-(1,2-Epoxyethyl)-7-oxabicyclo(4.1.0)heptane	ChEBI
4-(Epoxyethyl)-7-oxabicyclo(4.1.0)heptane	ChEBI
4-Vinyl-1,2-cyclohexene diepoxide	ChEBI
4-Vinyl-1-cyclohexene dioxide	ChEBI
4-Vinylcyclohexene diepoxide	ChEBI
Vinyl cyclohexene diepoxide	ChEBI
Vinyl cyclohexene dioxide	ChEBI
Vinyl cyclohexane diepoxide	MeSH
Vinylcyclohexene diepoxide	MeSH

Chemical Formula

C₈H₁₂O₂

Average Molecular Weight

140.182

Monoisotopic Molecular Weight

140.083729626

IUPAC Name

3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane

Traditional Name

4-vinylcyclohexene diepoxide

CAS Registry Number

Not Available

SMILES

C1OC1C1CCC2OC2C1

InChI Identifier

InChI=1S/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2

InChI Key

OECTYKWYRCHAKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:59001 )

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	0.85	ALOGPS
logP	0.83	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.98 m³·mol⁻¹	ChemAxon
Polarizability	15.06 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	130.47	30932474
DeepCCS	[M-H]-	127.625	30932474
DeepCCS	[M-2H]-	164.356	30932474
DeepCCS	[M+Na]+	139.429	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.4	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	131.7	32859911
AllCCS	[M+Na-2H]-	132.5	32859911
AllCCS	[M+HCOO]-	133.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.1754 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.73 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1911.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	482.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	290.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	581.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	556.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1066.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	343.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1236.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	548.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	479.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	81.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Vinylcyclohexene dioxide	C1OC1C1CCC2OC2C1	1957.4	Standard polar	33892256
4-Vinylcyclohexene dioxide	C1OC1C1CCC2OC2C1	1128.9	Standard non polar	33892256
4-Vinylcyclohexene dioxide	C1OC1C1CCC2OC2C1	1276.2	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 - 4-Vinylcyclohexene dioxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001u-9100000000-f6c6162e373bc108d768	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Vinylcyclohexene dioxide 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 - 4-Vinylcyclohexene dioxide 10V, Positive-QTOF	splash10-0006-1900000000-25aa30120532b97dac50	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 20V, Positive-QTOF	splash10-022c-4900000000-54b4fa8f2faf159b72f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 40V, Positive-QTOF	splash10-014m-9000000000-7f59f84070d389cadadc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 10V, Negative-QTOF	splash10-000i-0900000000-75e71238d9c47d0f494f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 20V, Negative-QTOF	splash10-000i-1900000000-9f89c997df990feafc3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 40V, Negative-QTOF	splash10-00ke-9000000000-983862341ae3c6bb7483	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 10V, Positive-QTOF	splash10-0006-0900000000-9b661c4faae5dc66ee0e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 20V, Positive-QTOF	splash10-00dl-0900000000-e7a7f2df4dc3ff3443bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 40V, Positive-QTOF	splash10-006x-1900000000-fe5566847d4a99e29e2c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 10V, Negative-QTOF	splash10-000i-2900000000-20de1726e0e3ee3aafe6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 20V, Negative-QTOF	splash10-000i-0900000000-32c463be54c70cefde5d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Vinylcyclohexene dioxide 40V, Negative-QTOF	splash10-000l-6900000000-ec83bb2ac056227ac759	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
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, 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	¹H NMR Spectrum (1D, 400 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	¹³C NMR Spectrum (1D, 500 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	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	¹H NMR Spectrum (1D, 800 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, 900 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

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

7545

KEGG Compound ID

C19311

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vinylcyclohexene dioxide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

59001

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 4-Vinylcyclohexene dioxide (HMDB0246593)

MOL for HMDB0246593 (4-Vinylcyclohexene dioxide)

3D MOL for HMDB0246593 (4-Vinylcyclohexene dioxide)

3D SDF for HMDB0246593 (4-Vinylcyclohexene dioxide)

3D-SDF for HMDB0246593 (4-Vinylcyclohexene dioxide)

PDB for HMDB0246593 (4-Vinylcyclohexene dioxide)

3D PDB for HMDB0246593 (4-Vinylcyclohexene dioxide)

SMILES for HMDB0246593 (4-Vinylcyclohexene dioxide)

INCHI for HMDB0246593 (4-Vinylcyclohexene dioxide)

Structure for HMDB0246593 (4-Vinylcyclohexene dioxide)

3D Structure for HMDB0246593 (4-Vinylcyclohexene dioxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra