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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 02:54:55 UTC

Update Date

2021-09-23 02:54:55 UTC

HMDB ID

HMDB0301835

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(Z)-3,5-Hexadienyl butyrate

Description

(z)-3,5-hexadienyl butyrate is a member of the class of compounds known as fatty acid esters. Fatty acid esters are carboxylic ester derivatives of a fatty acid (z)-3,5-hexadienyl butyrate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (z)-3,5-hexadienyl butyrate can be found in passion fruit, which makes (z)-3,5-hexadienyl butyrate a potential biomarker for the consumption of this food product.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       7.287  -1.127   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.954  -3.437   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.953  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.953  -1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.286  -0.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.286   1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.288  -3.437   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    2   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0301835
HETATM    1  C1  UNL     1      -5.441  -0.517  -0.526  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.210  -0.085  -0.331  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.911   0.660   0.862  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.713   1.107   1.103  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.601   0.887   0.191  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.542   0.106   1.001  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.541  -0.116   0.136  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.698  -0.783   0.484  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.807  -1.230   1.650  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.828  -1.003  -0.452  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.873   0.064  -0.102  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.087  -0.020  -0.963  1.00  0.00           C  
HETATM   13  H1  UNL     1      -5.698  -1.074  -1.402  1.00  0.00           H  
HETATM   14  H2  UNL     1      -6.191  -0.301   0.209  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.518  -0.343  -1.117  1.00  0.00           H  
HETATM   16  H4  UNL     1      -4.742   0.840   1.570  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.506   1.674   2.017  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.084   1.870  -0.034  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.756   0.290  -0.690  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.318   0.720   1.874  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.057  -0.814   1.322  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.230  -2.023  -0.312  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.532  -0.851  -1.514  1.00  0.00           H  
HETATM   24  H12 UNL     1       4.070   0.052   0.979  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.360   1.046  -0.317  1.00  0.00           H  
HETATM   26  H14 UNL     1       4.942  -0.803  -1.722  1.00  0.00           H  
HETATM   27  H15 UNL     1       5.971  -0.303  -0.351  1.00  0.00           H  
HETATM   28  H16 UNL     1       5.350   0.951  -1.440  1.00  0.00           H  
CONECT    1    2    2   13   14
CONECT    2    3   15
CONECT    3    4    4   16
CONECT    4    5   17
CONECT    5    6   18   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
(3Z)-Hexa-3,5-dien-1-yl butanoic acid	Generator
(Z)-3,5-Hexadienyl butyric acid	Generator

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

(3Z)-hexa-3,5-dien-1-yl butanoate

Traditional Name

(Z)-3,5-hexadienyl butyrate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OCC\C=C/C=C

InChI Identifier

InChI=1S/C10H16O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3,5-6H,1,4,7-9H2,2H3/b6-5-

InChI Key

USOPMHKCANPDTP-WAYWQWQTSA-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

butyrate ester (CHEBI:453 )
fatty acid ester (CHEBI:453 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301835)

Food

Fruit

Tropical fruit

Passion fruit (FooDB: FOOD00128)

Process

Not Available

Role

Not Available

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
logP	3.03	ALOGPS
logP	2.61	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	7	ChemAxon
Refractivity	50.88 m³·mol⁻¹	ChemAxon
Polarizability	19.47 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
AllCCS	[M+H]+	142.261	32859911
AllCCS	[M+H-H2O]+	138.4	32859911
AllCCS	[M+Na]+	146.889	32859911
AllCCS	[M+NH4]+	145.854	32859911
AllCCS	[M-H]-	142.352	32859911
AllCCS	[M+Na-2H]-	144.086	32859911
AllCCS	[M+HCOO]-	146.065	32859911
DeepCCS	[M+H]+	138.692	30932474
DeepCCS	[M-H]-	135.224	30932474
DeepCCS	[M-2H]-	172.445	30932474
DeepCCS	[M+Na]+	147.82	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.5881 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.66 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2236.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	526.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	369.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	673.9 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	666.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	87.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1448.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	487.6 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	1369.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	486.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	464.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	497.9 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	12.0 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 10V, Positive-QTOF	splash10-014i-7900000000-26b6ca9ecf2ac5008404	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 20V, Positive-QTOF	splash10-0089-9100000000-4a2cc37e87b379a0f397	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 40V, Positive-QTOF	splash10-0f7o-9000000000-bd74d359c794e436132a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 10V, Negative-QTOF	splash10-014i-9700000000-c9c51c185265654f354f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 20V, Negative-QTOF	splash10-014r-9100000000-a88d4d7f6cd877b2cd81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 40V, Negative-QTOF	splash10-00kf-9000000000-6c16de3fd3787eb1a7a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 10V, Positive-QTOF	splash10-003r-9000000000-3cca127c6a4d1a9c77fd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 20V, Positive-QTOF	splash10-00pi-9000000000-918d6be289152aa61143	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 40V, Positive-QTOF	splash10-0f7o-9000000000-cd0ba39288173c335707	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 10V, Negative-QTOF	splash10-0002-9200000000-6365d50bbc534df991b0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 20V, Negative-QTOF	splash10-000i-9000000000-665af95c61484630f110	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-3,5-Hexadienyl butyrate 40V, Negative-QTOF	splash10-014i-9000000000-a1e6c8aff1e8a5723e88	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for (Z)-3,5-Hexadienyl butyrate (HMDB0301835)

MOL for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

3D MOL for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

3D SDF for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

3D-SDF for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

PDB for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

3D PDB for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

SMILES for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

INCHI for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

Structure for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

3D Structure for HMDB0301835 ((Z)-3,5-Hexadienyl butyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra