NP-MRD: Showing NP-Card for Ethyl alpha-linolenate (NP0046081)

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Record Information

Version

2.0

Created at

2022-03-17 19:48:04 UTC

Updated at

2022-03-17 19:48:04 UTC

NP-MRD ID

NP0046081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethyl alpha-linolenate

Description

Ethyl alpha-linolenate, also known as linolenate, ethyl ester or ethyl a-linolenic acid, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Ethyl alpha-linolenate is found in Aglaia odorata, Aristolochia fontanesii, Bidens pilosa, Daphne odora, Glycyrrhiza glabra and Lantana ukambensis. Ethyl alpha-linolenate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214312D          

 22 21  0  0  0  0            999 V2000
    6.3576   -3.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9286   -3.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -2.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997   -1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997   -1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9286    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3576    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7865    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5010    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2154    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9299    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6444    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3589    0.2273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6444    1.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0734    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7878    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h5-6,8-9,11-12H,3-4,7,10,13-19H2,1-2H3/b6-5-,9-8-,12-11-

> <INCHI_KEY>
JYYFMIOPGOFNPK-AGRJPVHOSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.4828

> <EXACT_MASS>
306.255880332

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
38.57223162600934

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

> <ALOGPS_LOGP>
6.77

> <JCHEM_LOGP>
6.562657148333335

> <ALOGPS_LOGS>
-6.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032123337017807

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
99.1531

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.49e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl linolenate

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      11.868  -6.506   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.534  -5.736   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.200  -6.506   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.866  -5.736   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.866  -4.196   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.533  -3.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.533  -1.886   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.866  -1.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.866   0.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.200   1.194   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.534   0.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.868   1.194   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.201   0.424   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.535   1.194   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.869   0.424   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.202   1.194   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.536   0.424   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.870   1.194   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      21.203   0.424   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      19.870   2.734   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      22.537   1.194   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.871   0.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
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   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
Ethyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate	ChEBI
Ethyl (9Z,12Z,15Z)-octadecatrienoate	ChEBI
Ethyl (Z,Z,Z)-9,12,15-octadecatrienoate	ChEBI
Ethyl cis,cis,cis-9,12,15-octadecatrienoate	ChEBI
Linolenic acid, ethyl ester	ChEBI
Ethyl (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid	Generator
Ethyl (9Z,12Z,15Z)-octadecatrienoic acid	Generator
Ethyl (Z,Z,Z)-9,12,15-octadecatrienoic acid	Generator
Ethyl cis,cis,cis-9,12,15-octadecatrienoic acid	Generator
Linolenate, ethyl ester	Generator
Ethyl a-linolenate	Generator
Ethyl a-linolenic acid	Generator
Ethyl alpha-linolenic acid	Generator
Ethyl α-linolenate	Generator
Ethyl α-linolenic acid	Generator
Linolenic acid ethyl ester	MeSH

Chemical Formula

C₂₀H₃₄O₂

Average Mass

306.4828 Da

Monoisotopic Mass

306.25588 Da

IUPAC Name

ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

Traditional Name

ethyl linolenate

CAS Registry Number

1191-41-9

SMILES

CCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C20H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h5-6,8-9,11-12H,3-4,7,10,13-19H2,1-2H3/b6-5-,9-8-,12-11-

InChI Key

JYYFMIOPGOFNPK-AGRJPVHOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aglaia odorata	LOTUS Database	35616633
Aristolochia longa	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Lantana ukambensis	LOTUS Database	35616633
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
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

long-chain fatty acid ethyl ester (CHEBI:84851 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	6.77	ALOGPS
logP	6.56	ChemAxon
logS	-6.8	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	15	ChemAxon
Refractivity	99.15 m³·mol⁻¹	ChemAxon
Polarizability	38.57 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002946

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5367460

PDB ID

Not Available

ChEBI ID

84851

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ethyl alpha-linolenate (NP0046081)

MOL for NP0046081 (Ethyl alpha-linolenate)

3D MOL for NP0046081 (Ethyl alpha-linolenate)

3D SDF for NP0046081 (Ethyl alpha-linolenate)

3D-SDF for NP0046081 (Ethyl alpha-linolenate)

PDB for NP0046081 (Ethyl alpha-linolenate)

3D PDB for NP0046081 (Ethyl alpha-linolenate)

SMILES for NP0046081 (Ethyl alpha-linolenate)

INCHI for NP0046081 (Ethyl alpha-linolenate)

Structure for NP0046081 (Ethyl alpha-linolenate)

3D Structure for NP0046081 (Ethyl alpha-linolenate)