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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:07 UTC

Update Date

2023-02-21 17:21:53 UTC

HMDB ID

HMDB0032312

Secondary Accession Numbers

HMDB32312

Metabolite Identification

Common Name

2,4-Hexadienyl butyrate

Description

2,4-Hexadienyl butyrate 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 2,4-Hexadienyl butyrate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.186  -4.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.516   0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.852  -3.286   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.852  -1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.518  -0.976   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.518   0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.517   1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.517   2.874   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.851   0.564   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    4   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0032312
HETATM    1  C1  UNL     1      -5.394  -0.308   1.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.192   0.444   0.491  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.125  -0.193   0.071  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.937   0.489  -0.432  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.869  -0.143  -0.853  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.320   0.597  -1.358  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.456   0.291  -0.573  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.953  -0.996  -0.443  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.344  -1.918  -1.064  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.136  -1.230   0.390  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.599   0.082   0.975  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.956   1.061  -0.136  1.00  0.00           C  
HETATM   13  H1  UNL     1      -6.273   0.331   0.778  1.00  0.00           H  
HETATM   14  H2  UNL     1      -5.465  -1.299   0.507  1.00  0.00           H  
HETATM   15  H3  UNL     1      -5.295  -0.374   2.092  1.00  0.00           H  
HETATM   16  H4  UNL     1      -4.212   1.526   0.473  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.170  -1.287   0.116  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.946   1.569  -0.454  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.894  -1.228  -0.817  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.133   1.681  -1.231  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.565   0.334  -2.408  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.874  -1.905   1.227  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.933  -1.642  -0.258  1.00  0.00           H  
HETATM   24  H12 UNL     1       4.499  -0.141   1.587  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.815   0.497   1.644  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.182   1.833  -0.185  1.00  0.00           H  
HETATM   27  H15 UNL     1       4.969   1.459   0.063  1.00  0.00           H  
HETATM   28  H16 UNL     1       4.038   0.471  -1.076  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   16
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7   20   21
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4-Hexadienyl butyric acid	Generator
2,4-Hexadienol butanoate	HMDB
2,4-Hexadienol monobutyrate	HMDB
Butanoic acid, 2,4-hexadien-1-yl ester	HMDB
Butanoic acid, 2,4-hexadienyl ester	HMDB
Butyric acid, 2,4-hexadienyl ester	HMDB
Butyric acid, 2,4-hexadienyl ester (8ci)	HMDB
Hexa-2,4-dienyl butyrate	HMDB
Sorbyl butyrate	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

(2E,4E)-hexa-2,4-dien-1-yl butanoate

Traditional Name

(2E,4E)-hexa-2,4-dien-1-yl butanoate

CAS Registry Number

16930-93-1

SMILES

CCCC(=O)OC\C=C\C=C\C

InChI Identifier

InChI=1S/C10H16O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3,5-7H,4,8-9H2,1-2H3/b5-3+,7-6+

InChI Key

PTJGYWXDEDRLPB-TWTPFVCWSA-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

Wax monoesters (LMFA07010639 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032312)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032312)

Source

Endogenous

Endogenous (HMDB: HMDB0032312)

Animal

Animal (HMDB: HMDB0032312)

Exogenous

Food

Food (HMDB: HMDB0032312)

Exogenous (HMDB: HMDB0032312)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032312)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032312)

Lipid metabolism pathway (HMDB: HMDB0032312)

Cellular process

Cell signaling (HMDB: HMDB0032312)

Biochemical process

Lipid transport (HMDB: HMDB0032312)

Role

Biological role

Energy source (HMDB: HMDB0032312)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032312)

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	0.22 g/L	ALOGPS
logP	3.15	ALOGPS
logP	2.71	ChemAxon
logS	-2.9	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	6	ChemAxon
Refractivity	51.8 m³·mol⁻¹	ChemAxon
Polarizability	20.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	139.876	31661259
DarkChem	[M-H]-	139.224	31661259
DeepCCS	[M+H]+	136.942	30932474
DeepCCS	[M-H]-	133.568	30932474
DeepCCS	[M-2H]-	170.681	30932474
DeepCCS	[M+Na]+	146.157	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.8	32859911
AllCCS	[M+NH4]+	145.3	32859911
AllCCS	[M+Na]+	146.3	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	144.1	32859911
AllCCS	[M+HCOO]-	146.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Hexadienyl butyrate	CCCC(=O)OC\C=C\C=C\C	1767.8	Standard polar	33892256
2,4-Hexadienyl butyrate	CCCC(=O)OC\C=C\C=C\C	1259.2	Standard non polar	33892256
2,4-Hexadienyl butyrate	CCCC(=O)OC\C=C\C=C\C	1288.3	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 - 2,4-Hexadienyl butyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9000000000-c255a85c5aed81e4d206	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Hexadienyl butyrate 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 - 2,4-Hexadienyl butyrate 10V, Negative-QTOF	splash10-014i-9600000000-c5ec08bb27f5992f7867	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 20V, Negative-QTOF	splash10-014r-9100000000-e28e660a3bde7a3cc469	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 40V, Negative-QTOF	splash10-00kf-9000000000-495e02331e100607b478	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 10V, Negative-QTOF	splash10-00kb-9100000000-4475d53ec41fc0778152	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 20V, Negative-QTOF	splash10-000i-9000000000-8a7bd0ff6df792525036	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 40V, Negative-QTOF	splash10-014i-9000000000-4f3c2a9daf8b23dee035	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 10V, Positive-QTOF	splash10-0159-9700000000-ccaff10d82cc6f7bfb3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 20V, Positive-QTOF	splash10-001i-9000000000-11ac47ea15ecb728389d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 40V, Positive-QTOF	splash10-0uec-9000000000-f2da41d6e1ba017ff849	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 10V, Positive-QTOF	splash10-003r-9000000000-16d8086aa259c2aa0694	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 20V, Positive-QTOF	splash10-057i-9000000000-3c15cf83b08e25e867e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Hexadienyl butyrate 40V, Positive-QTOF	splash10-053u-9000000000-2f356cf3c027257169cb	2021-09-22	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

FDB009560

KNApSAcK ID

Not Available

Chemspider ID

5020873

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6537958

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2,4-Hexadienyl butyrate (HMDB0032312)

MOL for HMDB0032312 (2,4-Hexadienyl butyrate)

3D MOL for HMDB0032312 (2,4-Hexadienyl butyrate)

3D SDF for HMDB0032312 (2,4-Hexadienyl butyrate)

3D-SDF for HMDB0032312 (2,4-Hexadienyl butyrate)

PDB for HMDB0032312 (2,4-Hexadienyl butyrate)

3D PDB for HMDB0032312 (2,4-Hexadienyl butyrate)

SMILES for HMDB0032312 (2,4-Hexadienyl butyrate)

INCHI for HMDB0032312 (2,4-Hexadienyl butyrate)

Structure for HMDB0032312 (2,4-Hexadienyl butyrate)

3D Structure for HMDB0032312 (2,4-Hexadienyl butyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra