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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:16:00 UTC

Update Date

2023-02-21 17:25:14 UTC

HMDB ID

HMDB0036208

Secondary Accession Numbers

HMDB36208

Metabolite Identification

Common Name

2-Propenyl 2-ethylbutanoate

Description

2-Propenyl 2-ethylbutanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on 2-Propenyl 2-ethylbutanoate.

Structure

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

COMPND    HMDB0036208
HETATM    1  C1  UNL     1       4.645   0.525   0.417  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.709  -0.075  -0.313  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.605  -0.853   0.313  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.393  -0.253  -0.071  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.143  -0.664   0.292  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.037  -1.669   1.038  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.085   0.036  -0.166  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.341  -0.593   0.359  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.526  -2.012  -0.047  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.971   1.467   0.320  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.195   2.226  -0.118  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.632   0.466   1.518  1.00  0.00           H  
HETATM   13  H2  UNL     1       5.457   1.094   0.000  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.796   0.034  -1.393  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.635  -1.924   0.022  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.775  -0.828   1.408  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.108   0.063  -1.282  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.204   0.009   0.011  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.324  -0.468   1.474  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.706  -2.282  -0.753  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.488  -2.151  -0.601  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.493  -2.711   0.806  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.845   1.481   1.431  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.047   1.883  -0.144  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.505   1.930  -1.119  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.977   3.319  -0.059  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.013   1.951   0.606  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   14
CONECT    3    4   15   16
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   10   17
CONECT    8    9   18   19
CONECT    9   20   21   22
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Propenyl 2-ethylbutanoic acid	Generator
2-Propenyl 2-ethylbutyrate	HMDB
Allyl 2-ethyl butyrate	HMDB
Allyl 2-ethylbutanoate	HMDB
Allyl 2-ethylbutyrate	HMDB
Butanoic acid, 2-ethyl-, 2-propen-1-yl ester	HMDB
Butanoic acid, 2-ethyl-, 2-propenyl ester	HMDB
Butyric acid, 2-ethyl-, 2-propenyl ester	HMDB
Butyric acid, 2-ethyl-, allyl ester	HMDB
Butyric acid, 2-ethyl-, allyl ester (8ci)	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

prop-2-en-1-yl 2-ethylbutanoate

Traditional Name

prop-2-en-1-yl 2-ethylbutanoate

CAS Registry Number

7493-69-8

SMILES

CCC(CC)C(=O)OCC=C

InChI Identifier

InChI=1S/C9H16O2/c1-4-7-11-9(10)8(5-2)6-3/h4,8H,1,5-7H2,2-3H3

InChI Key

NBKXNUWCFMZFMM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0036208)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036208)

Source

Endogenous

Endogenous (HMDB: HMDB0036208)

Animal

Animal (HMDB: HMDB0036208)

Exogenous

Food

Food (HMDB: HMDB0036208)

Exogenous (HMDB: HMDB0036208)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036208)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036208)

Lipid metabolism pathway (HMDB: HMDB0036208)

Cellular process

Cell signaling (HMDB: HMDB0036208)

Biochemical process

Lipid transport (HMDB: HMDB0036208)

Role

Biological role

Energy source (HMDB: HMDB0036208)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036208)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036208)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 167 °C	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	1.14 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.79	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-7.1	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	6	ChemAxon
Refractivity	44.98 m³·mol⁻¹	ChemAxon
Polarizability	18.15 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]+	136.451	31661259
DarkChem	[M-H]-	134.434	31661259
DeepCCS	[M+H]+	137.946	30932474
DeepCCS	[M-H]-	135.073	30932474
DeepCCS	[M-2H]-	172.017	30932474
DeepCCS	[M+Na]+	147.052	30932474
AllCCS	[M+H]+	139.1	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.9	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	142.6	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.	5.84 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4915 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2352.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	560.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	364.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	672.9 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	761.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	160.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1367.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	485.4 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	1505.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	492.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	524.9 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	19.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl 2-ethylbutanoate	CCC(CC)C(=O)OCC=C	1277.4	Standard polar	33892256
2-Propenyl 2-ethylbutanoate	CCC(CC)C(=O)OCC=C	1005.2	Standard non polar	33892256
2-Propenyl 2-ethylbutanoate	CCC(CC)C(=O)OCC=C	1042.9	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-Propenyl 2-ethylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9100000000-753e8295411468e511d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2-ethylbutanoate 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 - 2-Propenyl 2-ethylbutanoate 10V, Positive-QTOF	splash10-0a4l-8900000000-0be01589ca8ca713ed08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 20V, Positive-QTOF	splash10-0006-9100000000-d7b4be5213f3891fed0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 40V, Positive-QTOF	splash10-0006-9000000000-6f0ca53871912e76e716	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 10V, Negative-QTOF	splash10-0a4i-3900000000-5be9470a61fcb0cad29e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 20V, Negative-QTOF	splash10-01b9-8900000000-384dd6a62aa2683536d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 40V, Negative-QTOF	splash10-00y0-9100000000-a0ee54461bdd853d2696	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 10V, Negative-QTOF	splash10-066r-0900000000-65fb7313fb8303ee8e6f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 20V, Negative-QTOF	splash10-014i-3900000000-a356d4055c0694d1843e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 40V, Negative-QTOF	splash10-0a4j-9000000000-0336c75f59947f5f5058	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 10V, Positive-QTOF	splash10-00r7-9200000000-6dbcf773052cb6482bf1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 20V, Positive-QTOF	splash10-006x-9000000000-aa5db86a64d32433719b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-ethylbutanoate 40V, Positive-QTOF	splash10-0006-9000000000-75cdb1962dba2b892292	2021-09-24	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB015066

KNApSAcK ID

Not Available

Chemspider ID

55337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61408

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-Propenyl 2-ethylbutanoate (HMDB0036208)

MOL for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

3D MOL for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

3D SDF for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

3D-SDF for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

PDB for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

3D PDB for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

SMILES for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

INCHI for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

Structure for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

3D Structure for HMDB0036208 (2-Propenyl 2-ethylbutanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra