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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:05 UTC

Update Date

2023-02-21 17:22:15 UTC

HMDB ID

HMDB0032491

Secondary Accession Numbers

HMDB32491

Metabolite Identification

Common Name

Prenyl isobutyrate

Description

Prenyl isobutyrate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Prenyl isobutyrate is a berry, butter, and fruity tasting compound. Based on a literature review very few articles have been published on Prenyl isobutyrate.

Structure

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

COMPND    HMDB0032491
HETATM    1  C1  UNL     1      -3.951   1.509  -0.643  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.957   0.450  -0.363  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.160  -0.934  -0.822  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.864   0.766   0.316  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.807  -0.236   0.645  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.404   0.197   0.059  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.528  -0.629   0.263  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.411  -1.683   0.935  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.842  -0.271  -0.305  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.837  -1.340   0.081  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.281   1.072   0.274  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.690   2.057  -1.560  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.968   1.093  -0.772  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.943   2.239   0.205  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.385  -1.246  -1.581  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.123  -1.643   0.008  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.134  -1.013  -1.381  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.680   1.783   0.672  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.716  -0.291   1.759  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.038  -1.231   0.214  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.801  -0.132  -1.408  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.479  -2.320  -0.241  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.860  -1.351   1.209  1.00  0.00           H  
HETATM   24  H13 UNL     1       4.846  -1.079  -0.327  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.404   1.733   0.237  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.628   0.980   1.318  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.094   1.522  -0.343  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   11   21
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Prenyl isobutyric acid	Generator
3-Methylbut-2-enyl isobutyrate	HMDB
Propanoic acid, 2-methyl-, 3-methyl-2-buten-1-yl ester	HMDB
Propanoic acid, 2-methyl-, 3-methyl-2-butenyl ester	HMDB
3-Methylbut-2-en-1-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

3-methylbut-2-en-1-yl 2-methylpropanoate

Traditional Name

3-methylbut-2-en-1-yl 2-methylpropanoate

CAS Registry Number

76649-23-5

SMILES

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

InChI Identifier

InChI=1S/C9H16O2/c1-7(2)5-6-11-9(10)8(3)4/h5,8H,6H2,1-4H3

InChI Key

YSJHMPXIMIOXGU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
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

Source

Endogenous

Endogenous (HMDB: HMDB0032491)

Exogenous

Food

Food (HMDB: HMDB0032491)

Exogenous (HMDB: HMDB0032491)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0032491)

Role

Biological role

Energy source (HMDB: HMDB0032491)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032491)

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
Water Solubility	4.34 g/L	ALOGPS
logP	2.96	ALOGPS
logP	2.53	ChemAxon
logS	-1.6	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	4	ChemAxon
Refractivity	45.73 m³·mol⁻¹	ChemAxon
Polarizability	18.58 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]+	138.433	31661259
DarkChem	[M-H]-	132.84	31661259
DeepCCS	[M+H]+	140.8	30932474
DeepCCS	[M-H]-	138.092	30932474
DeepCCS	[M-2H]-	174.399	30932474
DeepCCS	[M+Na]+	149.847	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	131.5	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.0	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	138.4	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prenyl isobutyrate	CC(C)C(=O)OCC=C(C)C	1331.5	Standard polar	33892256
Prenyl isobutyrate	CC(C)C(=O)OCC=C(C)C	1010.7	Standard non polar	33892256
Prenyl isobutyrate	CC(C)C(=O)OCC=C(C)C	1065.2	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 - Prenyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9000000000-5e709183ee493c546e35	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prenyl isobutyrate 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 - Prenyl isobutyrate 10V, Positive-QTOF	splash10-0aor-9800000000-367aae9a1139fe60c7d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Positive-QTOF	splash10-014i-9100000000-8ec13639477cdcbc9cd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Positive-QTOF	splash10-0603-9000000000-84b293b45aa3afdbe0a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Negative-QTOF	splash10-0a4i-6900000000-bbf81a5e204dcdd7ee18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Negative-QTOF	splash10-000i-9100000000-8b79b14d7f541ea9c02c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Negative-QTOF	splash10-00kr-9000000000-be6621fcec4a97563b34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Negative-QTOF	splash10-000i-9000000000-e4cb211981804e9150f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Negative-QTOF	splash10-000i-9000000000-f0d1d76a3ff0244e0bf0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Negative-QTOF	splash10-00dr-9000000000-870c94464becec2e2693	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Positive-QTOF	splash10-014i-9000000000-455ac7e6cbb6b6b26845	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Positive-QTOF	splash10-014l-9000000000-bafdab33b4d3558bdebf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Positive-QTOF	splash10-0006-9000000000-bcb4ebb7f9d789d208c6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB010137

KNApSAcK ID

Not Available

Chemspider ID

151464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

173535

PDB ID

Not Available

ChEBI ID

206353

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

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for Prenyl isobutyrate (HMDB0032491)

MOL for HMDB0032491 (Prenyl isobutyrate)

3D MOL for HMDB0032491 (Prenyl isobutyrate)

3D SDF for HMDB0032491 (Prenyl isobutyrate)

3D-SDF for HMDB0032491 (Prenyl isobutyrate)

PDB for HMDB0032491 (Prenyl isobutyrate)

3D PDB for HMDB0032491 (Prenyl isobutyrate)

SMILES for HMDB0032491 (Prenyl isobutyrate)

INCHI for HMDB0032491 (Prenyl isobutyrate)

Structure for HMDB0032491 (Prenyl isobutyrate)

3D Structure for HMDB0032491 (Prenyl isobutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra