MiMeDB: Showing metabocard for Ethyl 2-hexenoate (MMDBc0033413)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:47:33 UTC

Update Date

2022-08-31 22:35:54 UTC

Metabolite ID

MMDBc0033413

Metabolite Identification

Common Name

Ethyl 2-hexenoate

Description

Ethyl 2-hexenoate is a volatile ethyl ester found in wine and produced during fermentation by yeast. Ethyl esters are formed by the reaction of ethanol with a fatty acid. They typically have pleasant sweet aromas. The concentrations of ethyl ester decrease over time as a wine ages due to spontaneous hydrolysis.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311192105472D          

 24 23  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -1.5381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768   -1.1678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2855    0.1091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268   -0.2611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747    1.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747    2.5137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033413

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(=C([H])C([H])([H])C([H])([H])C([H])([H])[H])C(=O)OC([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O2/c1-3-5-6-7-8(9)10-4-2/h6-7H,3-5H2,1-2H3

> <INCHI_KEY>
SJRXWMQZUAOMRJ-UHFFFAOYSA-N

> <FORMULA>
C8H14O2

> <MOLECULAR_WEIGHT>
142.198

> <EXACT_MASS>
142.099379691

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.345125178914305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl hex-2-enoate

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.544754961333333

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7909905062381055

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
41.684599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hexenoic acid, ethyl ester

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-NOV-21         0                                  
HETATM    1  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      -0.680  -2.871   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0       0.517  -2.180   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -2.400   0.204   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      -3.597  -0.487   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -4.414  -1.897   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0      -3.850  -4.001   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.746  -3.437   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       3.686   3.310   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.686   4.692   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       1.540   5.335   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       2.874   6.105   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.770   6.668   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.206   4.565   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
Ethyl 2-hexenoic acid	Generator

Molecular Formula

C₈H₁₄O₂

Average Mass

142.198

Monoisotopic Mass

142.099379691

IUPAC Name

ethyl hex-2-enoate

Traditional Name

2-hexenoic acid, ethyl ester

CAS Registry Number

1552-67-6

SMILES

[H]C(=C([H])C([H])([H])C([H])([H])C([H])([H])[H])C(=O)OC([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C8H14O2/c1-3-5-6-7-8(9)10-4-2/h6-7H,3-5H2,1-2H3

InChI Key

SJRXWMQZUAOMRJ-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
Alpha,beta-unsaturated carboxylic ester
Enoate 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 ethyl ester (CHEBI:87514 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.11 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.54	ChemAxon
logS	-2.1	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	5	ChemAxon
Refractivity	41.68 m³·mol⁻¹	ChemAxon
Polarizability	16.35 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

452821

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519129

PDB ID

Not Available

ChEBI ID

87514

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tsakiris A, Koutinas AA, Psarianos C, Kourkoutas Y, Bekatorou A: A new process for wine production by penetration of yeast in uncrushed frozen grapes. Appl Biochem Biotechnol. 2010 Oct;162(4):1109-21. doi: 10.1007/s12010-009-8881-8. Epub 2010 Feb 12. [PubMed:20151225 ]

Showing metabocard for Ethyl 2-hexenoate (MMDBc0033413)

MOL for #<Metabolite:0x00007fecf461e200>

3D MOL for #<Metabolite:0x00007fecf461e200>

3D SDF for #<Metabolite:0x00007fecf461e200>

3D-SDF for #<Metabolite:0x00007fecf461e200>

PDB for #<Metabolite:0x00007fecf461e200>

3D PDB for #<Metabolite:0x00007fecf461e200>

SMILES for #<Metabolite:0x00007fecf461e200>

INCHI for #<Metabolite:0x00007fecf461e200>

Structure for #<Metabolite:0x00007fecf461e200>

3D Structure for #<Metabolite:0x00007fecf461e200>