NP-MRD: Showing NP-Card for pinoleic acid (NP0292459)

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Record Information

Version

2.0

Created at

2022-09-10 00:00:01 UTC

Updated at

2022-09-10 00:00:01 UTC

NP-MRD ID

NP0292459

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pinoleic acid

Description

Pinolenic acid, also known as C18:3N-6,9,13 or pinolenate, 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. pinoleic acid is found in Pinus koraiensis and Teucrium cubense. pinoleic acid was first documented in 2018 (PMID: 30404964). Pinolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 32898315) (PMID: 31776889) (PMID: 31430456) (PMID: 30894460).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 49  0  0  0  0  0  0  0  0999 V2000
   -5.6257   -1.7193    1.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3606   -0.7305    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    0.4871    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103    1.5553    0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4409    1.1239   -0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1521    0.6909   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666    1.2281   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008    2.3639   -1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032    2.2311   -2.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755    1.1791   -2.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.1684   -2.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782   -0.5005   -2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.8531   -1.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241   -2.1465   -0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -1.1774    0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763   -1.3677    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.3109    1.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4441   -0.3752    2.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2746   -1.2261    1.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8922    0.5459    3.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810   -1.6080    2.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5460   -1.3966    2.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981   -2.7269    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7383   -1.2145   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3413   -0.4586    0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7690    0.2281    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.9275    2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349    2.4256    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3522    1.9014   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9002    0.1861   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4114    1.8839   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -0.1769    0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    0.8056    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    2.8269   -1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487    3.2461   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    3.2084   -3.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1498    1.3259   -3.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966   -0.8703   -3.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -0.4933   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6536   -0.5010   -3.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310    0.2474   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040   -2.7319   -2.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693   -3.2498   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948   -0.1497    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -1.2513    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3103   -1.3165   -0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7707   -2.3898    1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612    0.6749    1.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -0.4572    2.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5510    1.2746    2.9856 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  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
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 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


  Mrv1652309272006272D          

 20 19  0  0  0  0            999 V2000
10006.514210007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.229610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.946910007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.771310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.486110007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.200610007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.025610007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.740410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.454810007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.169410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.883910007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.598610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.800910007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.976310007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.261010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.545610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.832410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.117010007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.401610007.3668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.117010008.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  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
M  END
> <DATABASE_ID>
NP0292459

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/CC\C=C/CCCC(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/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13-

> <INCHI_KEY>
HXQHFNIKBKZGRP-URPRIDOGSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.436

> <EXACT_MASS>
278.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.27629904595861

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922347462675991

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pinolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8678.8268680.418   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8680.1628681.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8681.5018680.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8683.0408680.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8684.3748681.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8685.7088680.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8687.2488680.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8688.5828681.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8689.9168680.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8691.2508681.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8692.5838680.418   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8693.9178681.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8677.4958681.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8675.9568681.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8674.6218680.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.2858681.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.9548680.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.6188681.188   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8669.2838680.418   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8670.6188682.726   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
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                                                            
CONECT   13    1   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
5Z,9Z,12Z-Octadecatrienoic acid	ChEBI
all-cis-Octadeca-5,9,12-trienoic acid	ChEBI
C18:3N-6,9,13	ChEBI
cis,cis,cis-5,9,12-Octadecatrienoic acid	ChEBI
5Z,9Z,12Z-Octadecatrienoate	Generator
all-cis-Octadeca-5,9,12-trienoate	Generator
cis,cis,cis-5,9,12-Octadecatrienoate	Generator
Pinolenate	Generator
5,9,12-Octadecatrienoic acid, (Z,Z,e)-isomer	MeSH
trans-5,9,12-Octadecatrienoic acid	MeSH
5,9,12-Octadecatrienoic acid	MeSH
5,9,12-Octadecatrienoic acid, (cis)-isomer	MeSH
Columbinic acid	MeSH
(5Z,9Z,12Z)-Octadecatrienoic acid	PhytoBank
(Z,Z,Z)-5,9,12-Octadecatrienoic acid	PhytoBank
(5Z,9Z,12Z)-5,9,12-Octadecatrienoic acid	PhytoBank
5,9,12-cis-Octadecatrienoic acid	PhytoBank
Pinolenic acid	PhytoBank
PA	PhytoBank
FA(18:3(7Z,11Z,14Z))	PhytoBank

Chemical Formula

C₁₈H₃₀O₂

Average Mass

278.4360 Da

Monoisotopic Mass

278.22458 Da

IUPAC Name

(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid

Traditional Name

pinolenic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CC\C=C/CCCC(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/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13-

InChI Key

HXQHFNIKBKZGRP-URPRIDOGSA-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
Pinus koraiensis	LOTUS Database	35616633
Teucrium cubense	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

octadecatrienoic acid (CHEBI:86136 )
Unsaturated fatty acids (LMFA01030344 )

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	6.6	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.92	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	34.28 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

4471920

KEGG Compound ID

Not Available

BioCyc ID

CPD-14869

BiGG ID

Not Available

Wikipedia Link

Pinolenic_acid

METLIN ID

Not Available

PubChem Compound

5312495

PDB ID

Not Available

ChEBI ID

86136

Good Scents ID

Not Available

References

General References

Baker EJ, Valenzuela CA, van Dooremalen WTM, Martinez-Fernandez L, Yaqoob P, Miles EA, Calder PC: Gamma-Linolenic and Pinolenic Acids Exert Anti-Inflammatory Effects in Cultured Human Endothelial Cells Through Their Elongation Products. Mol Nutr Food Res. 2020 Oct;64(20):e2000382. doi: 10.1002/mnfr.202000382. Epub 2020 Sep 16. [PubMed:32898315 ]
Kim H, Choi N, Kim HR, Lee J, Kim IH: Preparation of High Purity Delta5-Olefinic Acids from Pine Nut Oil via Repeated Lipase-Catalyzed Esterification. J Oleo Sci. 2018;67(11):1435-1442. doi: 10.5650/jos.ess18136. [PubMed:30404964 ]
Chen SJ, Huang WC, Shen HJ, Chen RY, Chang H, Ho YS, Tsai PJ, Chuang LT: Investigation of Modulatory Effect of Pinolenic Acid (PNA) on Inflammatory Responses in Human THP-1 Macrophage-Like Cell and Mouse Models. Inflammation. 2020 Apr;43(2):518-531. doi: 10.1007/s10753-019-01134-7. [PubMed:31776889 ]
Zhang J, Zhang SD, Wang P, Guo N, Wang W, Yao LP, Yang Q, Efferth T, Jiao J, Fu YJ: Pinolenic acid ameliorates oleic acid-induced lipogenesis and oxidative stress via AMPK/SIRT1 signaling pathway in HepG2 cells. Eur J Pharmacol. 2019 Oct 15;861:172618. doi: 10.1016/j.ejphar.2019.172618. Epub 2019 Aug 17. [PubMed:31430456 ]
Yamaoka Y, Shin S, Choi BY, Kim H, Jang S, Kajikawa M, Yamano T, Kong F, Legeret B, Fukuzawa H, Li-Beisson Y, Lee Y: The bZIP1 Transcription Factor Regulates Lipid Remodeling and Contributes to ER Stress Management in Chlamydomonas reinhardtii. Plant Cell. 2019 May;31(5):1127-1140. doi: 10.1105/tpc.18.00723. Epub 2019 Mar 20. [PubMed:30894460 ]
LOTUS database [Link]

Showing NP-Card for pinoleic acid (NP0292459)

MOL for NP0292459 (pinoleic acid)

3D MOL for NP0292459 (pinoleic acid)

3D SDF for NP0292459 (pinoleic acid)

3D-SDF for NP0292459 (pinoleic acid)

PDB for NP0292459 (pinoleic acid)

3D PDB for NP0292459 (pinoleic acid)

SMILES for NP0292459 (pinoleic acid)

INCHI for NP0292459 (pinoleic acid)

Structure for NP0292459 (pinoleic acid)

3D Structure for NP0292459 (pinoleic acid)