MiMeDB: Showing metabocard for (8Z,11Z,14Z)-eicosatrienoic acid (MMDBc0054993)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:25 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0054993

Metabolite Identification

Common Name

(8Z,11Z,14Z)-eicosatrienoic acid

Description

(8Z,11Z,14Z)-eicosatrienoate, also known as (Z,Z,Z)-eicosa-8,11,14-trienoate or (8Z,11Z,14Z)-icosatrienoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Based on a literature review very few articles have been published on (8Z,11Z,14Z)-eicosatrienoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 28 27  0  0  0  0            999 V2000
    1.5521    6.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    6.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    5.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    4.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    4.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    3.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    2.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3382    3.6768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.1177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    0.8704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    2.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0627    1.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23  6  1  0  0  0  0
 24  7  1  0  0  0  0
 25  9  1  0  0  0  0
 26 10  1  0  0  0  0
 27 12  1  0  0  0  0
 28 13  1  0  0  0  0
M  CHG  1  22  -1
M  END


  Mrv1652306172221392D          

 28 27  0  0  0  0            999 V2000
    1.5521    6.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    6.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    5.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    4.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    4.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    3.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    2.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3382    3.6768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019    2.1177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    0.8704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    2.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0627    1.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23  6  1  0  0  0  0
 24  7  1  0  0  0  0
 25  9  1  0  0  0  0
 26 10  1  0  0  0  0
 27 12  1  0  0  0  0
 28 13  1  0  0  0  0
M  CHG  1  22  -1
M  END
> <DATABASE_ID>
MMDBc0054993

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/p-1/b7-6-,10-9-,13-12-

> <INCHI_KEY>
HOBAELRKJCKHQD-QNEBEIHSSA-M

> <FORMULA>
C20H33O2

> <MOLECULAR_WEIGHT>
305.483

> <EXACT_MASS>
305.248603883

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.1945059062367

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z,11Z,14Z)-icosa-8,11,14-trienoate

> <JCHEM_LOGP>
6.9490924676666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885823686047827

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
109.6745

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
cis-8,11,14-eicosatrienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       2.897  12.975   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.889  11.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.393  10.356   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.385   9.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.889   7.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.881   6.572   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.385   5.117   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.897   4.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.401   3.371   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.914   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.922   4.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.434   3.953   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.938   2.498   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.434  -0.121   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.946  -0.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.954   0.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.467   0.461   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.475   1.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.987   1.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.995   2.498   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.491  -0.121   0.000  0.00  0.00           O-1
HETATM   23  H   UNK     0      -0.631   6.863   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.377   3.953   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.393   2.207   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.418   1.625   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.442   5.117   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       9.450   2.207   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

Synonyms

Value	Source
(8Z,11Z,14Z)-Eicosa-8,11,14-trienoate	ChEBI
(8Z,11Z,14Z)-Icosatrienoate	ChEBI
(Z,Z,Z)-Eicosa-8,11,14-trienoate	ChEBI
(Z,Z,Z)-Icosa-8,11,14-trienoate	ChEBI
all-cis-8,11,14-Eicosatrienoate	ChEBI
all-cis-8,11,14-Icosatrienoate	ChEBI
Dihomo-gamma-linolenate	ChEBI
(8Z,11Z,14Z)-Eicosa-8,11,14-trienoic acid	Generator
(8Z,11Z,14Z)-Icosatrienoic acid	Generator
(Z,Z,Z)-Eicosa-8,11,14-trienoic acid	Generator
(Z,Z,Z)-Icosa-8,11,14-trienoic acid	Generator
all-cis-8,11,14-Eicosatrienoic acid	Generator
all-cis-8,11,14-Icosatrienoic acid	Generator
Dihomo-g-linolenate	Generator
Dihomo-g-linolenic acid	Generator
Dihomo-gamma-linolenic acid	Generator
Dihomo-γ-linolenate	Generator
Dihomo-γ-linolenic acid	Generator
(8Z,11Z,14Z)-Eicosatrienoic acid	Generator

Molecular Formula

C₂₀H₃₃O₂

Average Mass

305.483

Monoisotopic Mass

305.248603883

IUPAC Name

(8Z,11Z,14Z)-icosa-8,11,14-trienoate

Traditional Name

cis-8,11,14-eicosatrienoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCC([O-])=O

InChI Identifier

InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/p-1/b7-6-,10-9-,13-12-

InChI Key

HOBAELRKJCKHQD-QNEBEIHSSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

straight-chain fatty acid anion (CHEBI:71589 )
long-chain fatty acid anion (CHEBI:71589 )
polyunsaturated fatty acid anion (CHEBI:71589 )
icosatrienoate (CHEBI:71589 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	6.95	ChemAxon
pKa (Strongest Acidic)	4.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	109.67 m³·mol⁻¹	ChemAxon
Polarizability	38.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Bacteria	Proteobacteria	1	Human

Exposure Sources

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

20117973

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21158448

PDB ID

Not Available

ChEBI ID

71589

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (8Z,11Z,14Z)-eicosatrienoic acid (MMDBc0054993)

MOL for #<Metabolite:0x00007fdb13263a40>

3D MOL for #<Metabolite:0x00007fdb13263a40>

3D SDF for #<Metabolite:0x00007fdb13263a40>

3D-SDF for #<Metabolite:0x00007fdb13263a40>

PDB for #<Metabolite:0x00007fdb13263a40>

3D PDB for #<Metabolite:0x00007fdb13263a40>

SMILES for #<Metabolite:0x00007fdb13263a40>

INCHI for #<Metabolite:0x00007fdb13263a40>

Structure for #<Metabolite:0x00007fdb13263a40>

3D Structure for #<Metabolite:0x00007fdb13263a40>