NP-MRD: Showing NP-Card for eleostearic acid (NP0221246)

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Record Information

Version

2.0

Created at

2022-09-05 22:45:56 UTC

Updated at

2022-09-05 22:45:56 UTC

NP-MRD ID

NP0221246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eleostearic acid

Description

9,11,13-Octadecatrienoic acid, also known as C18:3 N-5,7,9 or eleostearic 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. eleostearic acid is found in Chrysobalanus icaco, Hyacinthoides non-scripta, Momordica charantia, Pleurocybella porrigens, Punica granatum and Telfairia occidentalis. 9,11,13-Octadecatrienoic acid is a weakly acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.0381    1.0787    1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2617   -0.0676    2.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8225    0.3376    2.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2536    0.7081    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300   -0.4535   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2956   -0.9987   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396   -0.5561   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -1.1474   -0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695   -0.6607   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -1.2430   -1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8716   -0.7351   -1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170   -1.8795   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0265   -1.4790   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7823   -1.0632   -1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2084   -0.6776   -1.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589    0.4721   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    1.7121   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6982    2.7770    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2685    2.5730    1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1732    4.0308    0.2317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6783    2.0546    1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1006    0.9811    1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0088    1.0576    0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6320   -0.3126    3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4065   -0.9528    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7314    1.2127    2.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032   -0.4689    2.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    1.4971    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2815    1.1450    1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3199   -0.8991   -0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257   -1.8611   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    0.2910    0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709   -1.9857   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.1823   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987   -2.0949   -1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8342    0.1582   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -0.5452   -2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -2.7719   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309   -2.2544    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5904   -2.2892    0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608   -0.6492    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641   -0.1964   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -1.8951   -2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7359   -0.4093   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6553   -1.5534   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288    0.6651    0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7827    0.2105    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103    1.5093   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0873    2.0869   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157    4.4193   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END


  Mrv1533004171505562D          

 20 19  0  0  0  0            999 V2000
   -4.1467    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   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  1  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  9  8  1  4  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  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC=CC=CC=CCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)

> <INCHI_KEY>
CUXYLFPMQMFGPL-UHFFFAOYSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.436

> <EXACT_MASS>
278.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.540164691360204

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octadeca-9,11,13-trienoic acid

> <ALOGPS_LOGP>
6.65

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eleostearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -7.740   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.407   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.073   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.739   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+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                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
9,11,13-Octadecatrienoic acids	ChEBI
C18:3 N-5,7,9	ChEBI
Eleostearic acid	ChEBI
N-9-Octadecatrienoic acid	ChEBI
Octadeca-9,11,13-trienoic acids	ChEBI
Eleostearate	Generator
N-9-Octadecatrienoate	Generator
9,11,13-Octadecatrienoate	Generator
9,11,13-Conjugated linolenic acid	MeSH
Eleostearic acid, (e,e,e)-isomer	MeSH
Eleostearic acid, (Z,Z,e)-isomer	MeSH
9cis,11trans,13trans-Conjugated linolenic acid	MeSH
Eleostearic acid, (Z,e,e)-isomer	MeSH
Trichosanic acid	MeSH
9C,11t,13t-CLN	MeSH
9,11,13-CLN	MeSH
Eleostearic acid, (e,Z,e)-isomer	MeSH
9,11,13-Octadecatrienoic acid	MeSH

Chemical Formula

C₁₈H₃₀O₂

Average Mass

278.4360 Da

Monoisotopic Mass

278.22458 Da

IUPAC Name

octadeca-9,11,13-trienoic acid

Traditional Name

eleostearic acid

CAS Registry Number

Not Available

SMILES

CCCCC=CC=CC=CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)

InChI Key

CUXYLFPMQMFGPL-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Chrysobalanus icaco	LOTUS Database	35616633
Hyacinthoides non-scripta	LOTUS Database	35616633
Momordica charantia	LOTUS Database	35616633
Pleurocybella porrigens	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Telfairia occidentalis	LOTUS Database	35616633

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
Long-chain fatty acid
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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

conjugated linolenic acid (CHEBI:38382 )

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	6.65	ALOGPS
logP	6.06	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	36.54 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

Not Available

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

93077

PDB ID

Not Available

ChEBI ID

38382

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for eleostearic acid (NP0221246)

MOL for NP0221246 (eleostearic acid)

3D MOL for NP0221246 (eleostearic acid)

3D SDF for NP0221246 (eleostearic acid)

3D-SDF for NP0221246 (eleostearic acid)

PDB for NP0221246 (eleostearic acid)

3D PDB for NP0221246 (eleostearic acid)

SMILES for NP0221246 (eleostearic acid)

INCHI for NP0221246 (eleostearic acid)

Structure for NP0221246 (eleostearic acid)

3D Structure for NP0221246 (eleostearic acid)