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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:44:50 UTC

Update Date

2023-02-21 17:25:51 UTC

HMDB ID

HMDB0037496

Secondary Accession Numbers

HMDB37496

Metabolite Identification

Common Name

Methyl (E)-2-octenoate

Description

Methyl (E)-2-octenoate 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 Methyl (E)-2-octenoate.

Structure

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

COMPND    HMDB0037496
HETATM    1  C1  UNL     1      -3.613  -0.237   0.785  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.644   0.878   0.597  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.306   0.446   0.084  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.370  -0.234  -1.250  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.082  -0.604  -1.616  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.636  -1.496  -0.602  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.669  -1.298   0.158  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.476  -0.115   0.129  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.262   0.839  -0.627  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.558  -0.013   0.984  1.00  0.00           O  
HETATM   11  C9  UNL     1       4.383   1.139   0.989  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.534  -1.041   0.050  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.640   0.180   0.701  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.558  -0.700   1.807  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.070   1.601  -0.120  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.484   1.395   1.562  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.745  -0.199   0.781  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.697   1.380  -0.059  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.911  -1.189  -1.181  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.791   0.443  -2.018  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.643   0.251  -1.936  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.076  -1.263  -2.540  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.096  -2.455  -0.478  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.929  -2.105   0.869  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.743   1.976   0.582  1.00  0.00           H  
HETATM   26  H15 UNL     1       4.710   1.357   2.018  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.251   1.065   0.335  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl (e)-2-octenoic acid	Generator
FEMA 3712	HMDB
Methyl 2-octenoate	HMDB
Methyl cis-2-octenoate	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

methyl (2Z)-oct-2-enoate

Traditional Name

methyl (2Z)-oct-2-enoate

CAS Registry Number

7367-81-9

SMILES

CCCCC\C=C/C(=O)OC

InChI Identifier

InChI=1S/C9H16O2/c1-3-4-5-6-7-8-9(10)11-2/h7-8H,3-6H2,1-2H3/b8-7-

InChI Key

CJBQSBZJDJHMLF-FPLPWBNLSA-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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl 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

Sweet

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0037496)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037496)

Source

Endogenous

Endogenous (HMDB: HMDB0037496)

Animal

Animal (HMDB: HMDB0037496)

Exogenous

Food

Food (HMDB: HMDB0037496)

Fruit

Pome

Pear (FooDB: FOOD00152)
Asian pear (FooDB: FOOD00291)

Exogenous (HMDB: HMDB0037496)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037496)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037496)

Lipid metabolism pathway (HMDB: HMDB0037496)

Cellular process

Cell signaling (HMDB: HMDB0037496)

Biochemical process

Lipid transport (HMDB: HMDB0037496)

Role

Biological role

Energy source (HMDB: HMDB0037496)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037496)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037496)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	89.00 to 91.00 °C. @ 9.00 mm Hg	The Good Scents Company Information System
Water Solubility	158.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.335 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	3.35	ALOGPS
logP	3.08	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-6.8	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	46.14 m³·mol⁻¹	ChemAxon
Polarizability	18.13 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]+	139.834	31661259
DarkChem	[M-H]-	135.346	31661259
DeepCCS	[M+H]+	131.216	30932474
DeepCCS	[M-H]-	127.313	30932474
DeepCCS	[M-2H]-	164.249	30932474
DeepCCS	[M+Na]+	140.023	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.0	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	142.3	32859911
AllCCS	[M+HCOO]-	144.5	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.	7.16 minutes	32390414
Predicted by Siyang on May 30, 2022	16.5013 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2243.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	529.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	362.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	675.5 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	662.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1506.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	487.3 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	1355.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	500.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	542.6 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	11.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl (E)-2-octenoate	CCCCC\C=C/C(=O)OC	1484.2	Standard polar	33892256
Methyl (E)-2-octenoate	CCCCC\C=C/C(=O)OC	1146.5	Standard non polar	33892256
Methyl (E)-2-octenoate	CCCCC\C=C/C(=O)OC	1229.2	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 - Methyl (E)-2-octenoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9200000000-1e522bdf5cb248dc7309	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (E)-2-octenoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (E)-2-octenoate 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 - Methyl (E)-2-octenoate 10V, Positive-QTOF	splash10-0a6r-0900000000-3a4cb5d84809fb4f084c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 20V, Positive-QTOF	splash10-053r-9400000000-175f3e83ea2d804e1000	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 40V, Positive-QTOF	splash10-052f-9000000000-37b1a955a8b18269f965	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 10V, Negative-QTOF	splash10-0a4i-0900000000-3721b0e72f54a1590187	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 20V, Negative-QTOF	splash10-0ab9-1900000000-d3453650fac0582554cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 40V, Negative-QTOF	splash10-0597-9300000000-2988a1fd5e13e3433612	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 10V, Negative-QTOF	splash10-0ab9-0900000000-c2dc1958bdb8e06d2e6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 20V, Negative-QTOF	splash10-0a4i-2900000000-eb271cfe5962e5e6db7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 40V, Negative-QTOF	splash10-014i-9000000000-0aa272c103654cb69880	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 10V, Positive-QTOF	splash10-0a4i-9200000000-3e016d078cd2b712816d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 20V, Positive-QTOF	splash10-0a4i-9000000000-4405234d22eb33bb9dad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (E)-2-octenoate 40V, Positive-QTOF	splash10-0a4l-9000000000-fe9faa164998ab877a0f	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

FDB016571

KNApSAcK ID

Not Available

Chemspider ID

9216105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11040937

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027691

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 Methyl (E)-2-octenoate (HMDB0037496)

MOL for HMDB0037496 (Methyl (E)-2-octenoate)

3D MOL for HMDB0037496 (Methyl (E)-2-octenoate)

3D SDF for HMDB0037496 (Methyl (E)-2-octenoate)

3D-SDF for HMDB0037496 (Methyl (E)-2-octenoate)

PDB for HMDB0037496 (Methyl (E)-2-octenoate)

3D PDB for HMDB0037496 (Methyl (E)-2-octenoate)

SMILES for HMDB0037496 (Methyl (E)-2-octenoate)

INCHI for HMDB0037496 (Methyl (E)-2-octenoate)

Structure for HMDB0037496 (Methyl (E)-2-octenoate)

3D Structure for HMDB0037496 (Methyl (E)-2-octenoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra