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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:19:06 UTC

Update Date

2023-02-21 17:26:19 UTC

HMDB ID

HMDB0038036

Secondary Accession Numbers

HMDB38036

Metabolite Identification

Common Name

2-Propenyl 3-methylbutanoate

Description

2-Propenyl 3-methylbutanoate, also known as allyl isovalerate or 2-propenyl isopentanoate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 2-Propenyl 3-methylbutanoate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Propenyl 3-methylbutanoate is a potentially toxic compound.

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-Propenyl 3-methylbutanoic acid	Generator
3-Methylbutanoic acid 2-propenyl ester	MeSH
2-Propenyl isopentanoate	HMDB
2-Propenyl isovalerate	HMDB
3-Methylbutanoic acid, 2-propenyl ester	HMDB
3-Methylbutyric acid, allyl ester	HMDB
Allyl 3-methylbutanoate	HMDB
Allyl 3-methylbutyrate	HMDB
Allyl isopentanoate	HMDB
Allyl isovalerate	HMDB, MeSH
Allyl isovalerianate	HMDB
Allylisovalerate	HMDB
Butanoic acid, 3-methyl-, 2-propen-1-yl ester	HMDB
Butanoic acid, 3-methyl-, 2-propenyl ester	HMDB
Butyric acid, 3-methyl-, allyl ester	HMDB
Isovaleric acid, allyl ester	HMDB

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

prop-2-en-1-yl 3-methylbutanoate

Traditional Name

allyl isovalerate

CAS Registry Number

2835-39-4

SMILES

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

InChI Identifier

InChI=1S/C8H14O2/c1-4-5-10-8(9)6-7(2)3/h4,7H,1,5-6H2,2-3H3

InChI Key

HOMAGVUCNZNWBC-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

fatty acid ester (CHEBI:82380 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0038036)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038036)

Source

Endogenous

Endogenous (HMDB: HMDB0038036)

Animal

Animal (HMDB: HMDB0038036)

Exogenous

Food

Food (HMDB: HMDB0038036)

Exogenous (HMDB: HMDB0038036)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038036)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038036)

Lipid metabolism pathway (HMDB: HMDB0038036)

Biochemical process

Lipid transport (HMDB: HMDB0038036)

Role

Biological role

Energy source (HMDB: HMDB0038036)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038036)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0038036)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	161.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	475.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.462 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.31 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.09	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-7	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	5	ChemAxon
Refractivity	40.35 m³·mol⁻¹	ChemAxon
Polarizability	16.15 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]+	131.774	31661259
DarkChem	[M-H]-	129.522	31661259
DeepCCS	[M+H]+	138.06	30932474
DeepCCS	[M-H]-	135.831	30932474
DeepCCS	[M-2H]-	172.12	30932474
DeepCCS	[M+Na]+	147.13	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	137.4	32859911
AllCCS	[M+Na]+	138.5	32859911
AllCCS	[M-H]-	133.5	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	138.6	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.	4.83 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2355 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2134.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	522.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	342.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	590.7 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	693.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	135.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1204.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.0 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	1394.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	483.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	498.6 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	34.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl 3-methylbutanoate	CC(C)CC(=O)OCC=C	1196.1	Standard polar	33892256
2-Propenyl 3-methylbutanoate	CC(C)CC(=O)OCC=C	924.2	Standard non polar	33892256
2-Propenyl 3-methylbutanoate	CC(C)CC(=O)OCC=C	969.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 3-methylbutanoate EI-B (Non-derivatized)	splash10-052u-9000000000-7354044a3e73badab547	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 3-methylbutanoate EI-B (Non-derivatized)	splash10-052u-9000000000-7354044a3e73badab547	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 3-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-8c72ffff21927ecdaed8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 3-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4u-9000000000-144259e1f020cb7f39b7	2014-09-20	Not Available	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 3-methylbutanoate 10V, Positive-QTOF	splash10-0006-9800000000-c1c58cf36f0fc42f665d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Positive-QTOF	splash10-0006-9000000000-79d35f58be29e09f9c34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Positive-QTOF	splash10-052f-9000000000-79e7855d5c6b4384458a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Negative-QTOF	splash10-000x-9800000000-2050888b2f1aa71760e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Negative-QTOF	splash10-0zgi-9500000000-62023d4b0cc8031ce800	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Negative-QTOF	splash10-0a5i-9000000000-74d59f47280519a970b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Negative-QTOF	splash10-0a4i-9100000000-9581f7dd0f1122c0bce5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Negative-QTOF	splash10-0a4i-9200000000-b681809035a014497157	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Negative-QTOF	splash10-053r-9100000000-bfa8683a2fd26729f60e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Positive-QTOF	splash10-0f7c-9500000000-5ccc91bfcd244fb82445	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Positive-QTOF	splash10-052f-9000000000-3546ef42470e2cefd611	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Positive-QTOF	splash10-052f-9000000000-5bb1bf863e5ad8e0b727	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

Cytoplasm
Extracellular

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

FDB017246

KNApSAcK ID

Not Available

Chemspider ID

16835

KEGG Compound ID

C19318

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17816

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1003061

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 3-methylbutanoate (HMDB0038036)

MOL for HMDB0038036 (2-Propenyl 3-methylbutanoate)

3D MOL for HMDB0038036 (2-Propenyl 3-methylbutanoate)

3D SDF for HMDB0038036 (2-Propenyl 3-methylbutanoate)

3D-SDF for HMDB0038036 (2-Propenyl 3-methylbutanoate)

PDB for HMDB0038036 (2-Propenyl 3-methylbutanoate)

3D PDB for HMDB0038036 (2-Propenyl 3-methylbutanoate)

SMILES for HMDB0038036 (2-Propenyl 3-methylbutanoate)

INCHI for HMDB0038036 (2-Propenyl 3-methylbutanoate)

Structure for HMDB0038036 (2-Propenyl 3-methylbutanoate)

3D Structure for HMDB0038036 (2-Propenyl 3-methylbutanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra