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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

2006-02-23 10:17:33 UTC

Update Date

2023-02-21 17:15:51 UTC

HMDB ID

HMDB0001862

Secondary Accession Numbers

HMDB01862

Metabolite Identification

Common Name

2-Ethylacrylic acid

Description

2-ethylacrylic acid is an alpha, beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by an ethyl group. It has a role as a mammalian metabolite. It derives from an acrylic acid. It is a conjugate acid of a 2-ethylacrylate. 2-Ethylacrylic acid is an intermediate metabolite in the conversion of R-2-methylbutyrate into 2-ethylhydracrylic acid, which is variably increased in defects of isoleucine oxidation at distal steps in the catabolic pathway (3-oxoacyl-CoA thiolase deficiency and methylmalonyl-CoA mutase deficiency) (PMID 1016232 ).

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-Ethyl-2-propenoic acid	ChEBI
2-Ethylpropenoic acid	ChEBI
alpha-Methylene-butanoic acid	ChEBI
2-Ethyl-2-propenoate	Generator
2-Ethylpropenoate	Generator
a-Methylene-butanoate	Generator
a-Methylene-butanoic acid	Generator
alpha-Methylene-butanoate	Generator
Α-methylene-butanoate	Generator
Α-methylene-butanoic acid	Generator
2-Ethylacrylate	Generator
2-Methylene-6ci,7ci,8ci)-butyrate	HMDB
2-Methylene-6ci,7ci,8ci)-butyric acid	HMDB
2-Methylenebutyrate	HMDB
2-Methylenebutyric acid	HMDB
Ethacrylate	HMDB
Ethacrylic acid	HMDB
Poly(2-ethylacrylic acid)	MeSH, HMDB
2-Ethyl acrylate	Generator, HMDB

Chemical Formula

C₅H₈O₂

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

IUPAC Name

2-methylidenebutanoic acid

Traditional Name

ethacrylic acid

CAS Registry Number

3586-58-1

SMILES

CCC(=C)C(O)=O

InChI Identifier

InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)

InChI Key

WROUWQQRXUBECT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Branched fatty acids

Alternative Parents

Substituents

Branched fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:84978 )
Branched fatty acids (LMFA01020111 )

Ontology

Not Available

Physical Properties

State

Solid

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	62.6 g/L	ALOGPS
logP	1.23	ALOGPS
logP	1.37	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	4.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.25 m³·mol⁻¹	ChemAxon
Polarizability	10.26 Å³	ChemAxon
Number of Rings	0	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]+	121.534	31661259
DarkChem	[M-H]-	114.416	31661259
AllCCS	[M+H]+	126.034	32859911
AllCCS	[M-H]-	124.176	32859911
DeepCCS	[M+H]+	127.52	30932474
DeepCCS	[M-H]-	124.722	30932474
DeepCCS	[M-2H]-	161.158	30932474
DeepCCS	[M+Na]+	135.733	30932474
AllCCS	[M+H]+	126.0	32859911
AllCCS	[M+H-H2O]+	121.7	32859911
AllCCS	[M+NH4]+	130.1	32859911
AllCCS	[M+Na]+	131.3	32859911
AllCCS	[M-H]-	124.2	32859911
AllCCS	[M+Na-2H]-	128.1	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.05 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5324 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	69.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1421.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	413.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	269.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	366.2 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	497.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	222.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	852.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	338.0 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	1075.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	542.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	366.5 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	116.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethylacrylic acid	CCC(=C)C(O)=O	1669.1	Standard polar	33892256
2-Ethylacrylic acid	CCC(=C)C(O)=O	873.3	Standard non polar	33892256
2-Ethylacrylic acid	CCC(=C)C(O)=O	844.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Ethylacrylic acid,1TMS,isomer #1	C=C(CC)C(=O)O[Si](C)(C)C	979.1	Semi standard non polar	33892256
2-Ethylacrylic acid,1TBDMS,isomer #1	C=C(CC)C(=O)O[Si](C)(C)C(C)(C)C	1203.2	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 - 2-Ethylacrylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zi0-9000000000-6b4a6a9b2cdfefbc13b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylacrylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9200000000-2de270e55791bfa7fd7f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylacrylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylacrylic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Ethylacrylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0zfr-9200000000-70057d2e916fe5d099e3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Ethylacrylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0k96-9000000000-404d85eb01c55fd5afcc	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Ethylacrylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-e2c0d6b93c24ab9497f9	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Positive-QTOF	splash10-0ue9-9600000000-ece9444150a982f96fa9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Positive-QTOF	splash10-0a59-9100000000-98d86f481b2b53f907ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-783f10b701ddd96d62d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Negative-QTOF	splash10-0002-9000000000-34b601fb3823c5cc58de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Negative-QTOF	splash10-0a4j-9000000000-eb97529a41ea9247efcd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Negative-QTOF	splash10-0pb9-9000000000-6388eb5218c3ba821c34	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Negative-QTOF	splash10-0002-9000000000-5289cc75fe7aae11de79	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Negative-QTOF	splash10-0002-9000000000-56ee768a1b761e35d2f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Negative-QTOF	splash10-0006-9000000000-1d7274ae3a0240fd0810	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Positive-QTOF	splash10-001i-9000000000-0cc8aed45af20d83ec92	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-2e3c92755ff0c48e1af8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Positive-QTOF	splash10-0a4r-9000000000-27e4bf52a3171b19db57	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Retinol Metabolism

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

FDB022716

KNApSAcK ID

Not Available

Chemspider ID

18085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

4141

PubChem Compound

19166

PDB ID

Not Available

ChEBI ID

84978

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Wang, Yan-jun; Wang, Yu-xia; Tang, Xiang-yang; Zhao, Wen-tao; Qi, Xin. Synthesis and characterization of 2-ethylacrylic acid. Shiyou Huagong (2003), 32(3), 251-253.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mamer OA, Tjoa SS, Scriver CR, Klassen GA: Demonstration of a new mammalian isoleucine catabolic pathway yielding an Rseries of metabolites. Biochem J. 1976 Dec 15;160(3):417-26. [PubMed:1016232 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

2-Ethylacrylic acid → 3,4,5-trihydroxy-6-[(2-methylidenebutanoyl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for 2-Ethylacrylic acid (HMDB0001862)

MOL for HMDB0001862 (2-Ethylacrylic acid)

3D MOL for HMDB0001862 (2-Ethylacrylic acid)

3D SDF for HMDB0001862 (2-Ethylacrylic acid)

3D-SDF for HMDB0001862 (2-Ethylacrylic acid)

PDB for HMDB0001862 (2-Ethylacrylic acid)

3D PDB for HMDB0001862 (2-Ethylacrylic acid)

SMILES for HMDB0001862 (2-Ethylacrylic acid)

INCHI for HMDB0001862 (2-Ethylacrylic acid)

Structure for HMDB0001862 (2-Ethylacrylic acid)

3D Structure for HMDB0001862 (2-Ethylacrylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions