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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:59:16 UTC

Update Date

2021-09-26 22:51:02 UTC

HMDB ID

HMDB0243756

Secondary Accession Numbers

None

Metabolite Identification

Common Name

[(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate

Description

[(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate, also known as glycidol methacrylate or 2,3-epoxypropanol methacrylate, belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position. Based on a literature review very few articles have been published on [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). [(2r)-oxiran-2-yl]methyl 2-methylprop-2-enoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 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
2,3-Epoxypropanol methacrylate	ChEBI
2,3-Epoxypropyl methacrylate	ChEBI
2-((Methacryloxy)methyl)oxirane	ChEBI
Glycidol methacrylate	ChEBI
Glycidyl alpha-methylacrylate	ChEBI
Methacrylic acid, 2,3-epoxypropyl ester	ChEBI
2,3-Epoxypropanol methacrylic acid	Generator
2,3-Epoxypropyl methacrylic acid	Generator
Glycidol methacrylic acid	Generator
Glycidyl a-methylacrylate	Generator
Glycidyl a-methylacrylic acid	Generator
Glycidyl alpha-methylacrylic acid	Generator
Glycidyl α-methylacrylate	Generator
Glycidyl α-methylacrylic acid	Generator
Methacrylate, 2,3-epoxypropyl ester	Generator
[(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoic acid	Generator
Glycidyl methacrylic acid	HMDB
Sta-lock	HMDB
Monomethacrylate propylene oxide	HMDB
Glycidyl methacrylate	HMDB

Chemical Formula

C₇H₁₀O₃

Average Molecular Weight

142.154

Monoisotopic Molecular Weight

142.062994182

IUPAC Name

(oxiran-2-yl)methyl 2-methylprop-2-enoate

Traditional Name

glycidyl methacrylate

CAS Registry Number

Not Available

SMILES

CC(=C)C(=O)OCC1CO1

InChI Identifier

InChI=1S/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3

InChI Key

VOZRXNHHFUQHIL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Enoate esters

Alternative Parents

Substituents

Enoate ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.72	ALOGPS
logP	1.15	ChemAxon
logS	-0.65	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.16 m³·mol⁻¹	ChemAxon
Polarizability	14.55 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
DeepCCS	[M+H]+	132.497	30932474
DeepCCS	[M-H]-	130.078	30932474
DeepCCS	[M-2H]-	166.082	30932474
DeepCCS	[M+Na]+	141.052	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	133.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.291 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.76 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1674.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	378.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	225.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	376.5 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	544.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	845.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	351.3 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	1196.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	505.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	374.1 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	110.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
[(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate	CC(=C)C(=O)OCC1CO1	1510.4	Standard polar	33892256
[(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate	CC(=C)C(=O)OCC1CO1	998.4	Standard non polar	33892256
[(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate	CC(=C)C(=O)OCC1CO1	1090.2	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 - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9000000000-8e4e22f316bbdfcd18e2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 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 - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 10V, Positive-QTOF	splash10-052f-7900000000-83b88ea887d57bdee4b1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 20V, Positive-QTOF	splash10-0a4l-9100000000-330983dc720f565052b8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 40V, Positive-QTOF	splash10-052f-9000000000-ed153c546be4c48e91d5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 10V, Negative-QTOF	splash10-000f-9700000000-6853c6dfa0f94ed66ea1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 20V, Negative-QTOF	splash10-000i-9100000000-acd8d07b3331ce56de4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 40V, Negative-QTOF	splash10-000i-9000000000-bd5e829879834d6082c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 10V, Positive-QTOF	splash10-05mo-9100000000-f246b8050d1ded10941c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 20V, Positive-QTOF	splash10-052f-9000000000-71231048599a429f7eca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 40V, Positive-QTOF	splash10-0006-9000000000-1ec4a6c4fb43803b09a3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 10V, Negative-QTOF	splash10-0079-9100000000-3927fba63fbc4e0150e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 20V, Negative-QTOF	splash10-052r-9000000000-b414029bb8dc77677115	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate 40V, Negative-QTOF	splash10-0006-9000000000-8411530b003ba0051965	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)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	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

7549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glycidyl_methacrylate

METLIN ID

Not Available

PubChem Compound

7837

PDB ID

Not Available

ChEBI ID

132844

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1248431

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 [(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate (HMDB0243756)

MOL for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

3D MOL for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

3D SDF for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

3D-SDF for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

PDB for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

3D PDB for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

SMILES for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

INCHI for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

Structure for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

3D Structure for HMDB0243756 ([(2R)-Oxiran-2-yl]methyl 2-methylprop-2-enoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra