NP-MRD: Showing NP-Card for Stearidonic acid (NP0045037)

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Record Information

Version

2.0

Created at

2022-03-10 18:53:08 UTC

Updated at

2022-03-10 22:22:29 UTC

NP-MRD ID

NP0045037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stearidonic acid

Description

Stearidonic acid, also known as SDA or stearidonate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Stearidonic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is biosynthesized from linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are the seed oils of hemp, blackcurrant and echium, and the cyanobacterium spirulina (a rich source of vitamins and minerals). Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) polyunsaturated fatty acids (PUFA). These oils appear to possess hypotriglyceridemic properties typically associated with fish oils (PMID: 15173404 ). Stearidonic acid may be used as a precursor to increase the eicosapentaenoic acid (EPA) content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition to influence cellular responses and functions in desirable ways (PMID: 15120716 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 47  0  0  0  0  0  0  0  0999 V2000
    5.9473    0.9360    1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2187   -0.0075    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925    0.2190    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9779    0.6335   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3288    0.9434   -1.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762    0.1944   -2.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949   -0.8186   -2.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865   -1.5811   -1.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -1.5677   -1.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749   -1.1824   -0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502   -0.7128    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8825    0.6877    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6692    1.1484    1.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    0.2477    2.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998    0.1568    2.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4882   -0.2990    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4787    0.4537    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3766   -0.2080   -0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975   -1.2214   -1.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6444    0.2858   -1.0501 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402    1.1818    0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.8753    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929    0.5007    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6438    0.1321   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -1.0546    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487    0.0280    1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980    0.8197   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586    0.9729   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0887    2.0677   -2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975    0.5830   -3.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7060   -1.2169   -3.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -2.6768   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -1.4474   -0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -1.9184   -2.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -1.2095   -1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -0.7953    0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.3991    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    1.3999   -0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154    2.2280    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013   -0.7126    2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    0.7814    3.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576    1.1709    3.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9308   -0.5012    3.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065   -1.3718    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5591   -0.4215    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446    0.6434   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9394    1.4700    0.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8437    1.0499   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  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
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 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
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 20 48  1  0
M  END


  Mrv1652303202019002D          

 20 19  0  0  0  0            999 V2000
   19.2651   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5506   -9.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8361   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1216   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4070   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6925   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9779   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2634   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5489   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8343   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1198   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4053   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6907   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9762   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2617   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5471   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8326   -9.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181   -9.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1181   -8.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4035   -9.4720    0.0000 O   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  2  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  2  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-

> <INCHI_KEY>
JIWBIWFOSCKQMA-LTKCOYKYSA-N

> <FORMULA>
C18H28O2

> <MOLECULAR_WEIGHT>
276.4137

> <EXACT_MASS>
276.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.10997676136738

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

> <ALOGPS_LOGP>
6.19

> <JCHEM_LOGP>
5.698033481

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922492763245736

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.752

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stearidonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      35.962 -17.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.628 -16.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.294 -17.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.960 -17.681   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.626 -16.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.293 -17.681   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.959 -17.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.625 -16.911   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.291 -17.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.957 -17.681   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.624 -16.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.290 -17.681   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.956 -17.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.622 -16.911   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.288 -17.681   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.955 -16.911   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.621 -17.681   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.287 -16.911   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.287 -15.371   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.953 -17.681   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
(6Z,9Z,12Z,15Z)-Octadecatetraenoic acid	ChEBI
6,9,12,15-Octadecatetraenoic acid	ChEBI
SDA	ChEBI
6Z,9Z,12Z,15Z-Octadecatetraenoic acid	Kegg
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid	Kegg
(6Z,9Z,12Z,15Z)-Octadecatetraenoate	Generator
6,9,12,15-Octadecatetraenoate	Generator
6Z,9Z,12Z,15Z-Octadecatetraenoate	Generator
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoate	Generator
Stearidonate	Generator
Stearidonic acid C18:4	HMDB
FA(18:4(6Z,9Z,12Z,15Z))	HMDB
FA(18:4n3)	HMDB
Moroctic acid	HMDB

Chemical Formula

C₁₈H₂₈O₂

Average Mass

276.4137 Da

Monoisotopic Mass

276.20893 Da

IUPAC Name

(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

Traditional Name

stearidonic acid

CAS Registry Number

20290-75-9

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O

InChI Identifier

InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-

InChI Key

JIWBIWFOSCKQMA-LTKCOYKYSA-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
Abelmoschus esculentus	FooDB	DTU Food
Abramis brama	FooDB	DTU Food
Acipenseridae	FooDB	DTU Food
Acrosiphonia coalita	LOTUS Database	35616633
Actinidia chinensis	FooDB	DTU Food
Agaricus bisporus	FooDB	DTU Food
Allium cepa L.	FooDB	DTU Food
Allium sativum	FooDB	DTU Food
Allium schoenoprasum	FooDB	DTU Food
Anacardium occidentale	FooDB	DTU Food
Ananas comosus	FooDB	DTU Food
Anarhichas lupus	FooDB	DTU Food
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	DTU Food
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	DTU Food
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	DTU Food
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arachis hypogaea	FooDB	DTU Food
Armoracia rusticana	FooDB	DTU Food
Asparagus officinalis	FooDB	DTU Food
Astacidea	FooDB	DTU Food
Avena sativa L.	FooDB	DTU Food
Averrhoa carambola	FooDB	DTU Food
Belone belone	FooDB	DTU Food
Bertholletia excelsa	FooDB	DTU Food
Beta vulgaris ssp. cicla	FooDB	DTU Food
Borago officinalis	LOTUS Database	35616633
Bos taurus	FooDB	DTU Food
Brachyura	FooDB	DTU Food
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. gemmifera	FooDB	DTU Food
Brassica oleracea var. gongylodes	FooDB	DTU Food
Brassica oleracea var. italica	FooDB	DTU Food
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. rapa	FooDB	DTU Food
Cannabis sativa	NULL	Not Available
Cantharellus cibarius	FooDB	DTU Food
Capsicum annuum	FooDB	DTU Food
Carica papaya L.	FooDB	DTU Food
Caridea	FooDB	DTU Food
Carthamus tinctorius	FooDB	DTU Food
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Cicer arietinum	FooDB	DTU Food
Cichorium endivia	FooDB	DTU Food
Cichorium intybus	FooDB	DTU Food
Cinnamomum	FooDB	DTU Food
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	DTU Food
Citrus limon	FooDB	DTU Food
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	DTU Food
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	DTU Food
Cladosiphon okamuranus	LOTUS Database	35616633
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Columbidae	FooDB	DTU Food
Coregonus	FooDB	DTU Food
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Cucumis melo	FooDB	DTU Food
Cucumis sativus L.	FooDB	DTU Food
Cucurbita	FooDB	DTU Food
Cucurbita maxima	FooDB	DTU Food
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	DTU Food
Cynara scolymus	FooDB	DTU Food
Daucus carota ssp. sativus	FooDB	DTU Food
Dioscorea	FooDB	DTU Food
Diospyros	FooDB	DTU Food
Echium plantagineum	LOTUS Database	35616633
Elaeis	FooDB	DTU Food
Engraulidae	FooDB	DTU Food
Eriobotrya japonica	FooDB	DTU Food
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Fagopyrum esculentum	FooDB	DTU Food
Ficus carica	FooDB	DTU Food
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gallus gallus	FooDB	DTU Food
Gastropoda	FooDB	DTU Food
Glycine max	FooDB	DTU Food
Gossypium	FooDB	DTU Food
Helianthus annuus L.	FooDB	DTU Food
Helianthus tuberosus	FooDB	DTU Food
Hippoglossus hippoglossus	FooDB	DTU Food
Homo sapiens (Serum)	Animalia	KNApSAcK
Hordeum vulgare	FooDB	DTU Food
Ipomoea batatas	FooDB	DTU Food
Juglans	FooDB	DTU Food
Juglans nigra L.	FooDB	DTU Food
Lactuca sativa	FooDB	DTU Food
Lagopus muta	FooDB	DTU Food
Lens culinaris	FooDB	DTU Food
Lepidium sativum	FooDB	DTU Food
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	DTU Food
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Malus	FooDB	DTU Food
Malus pumila	FooDB	DTU Food
Mangifera indica	FooDB	DTU Food
Manihot esculenta	FooDB	DTU Food
Medicago sativa	FooDB	DTU Food
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Merlangius merlangus	FooDB	DTU Food
Micromesistius poutassou	FooDB	DTU Food
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Mus musculus	LOTUS Database	35616633
Musa x paradisiaca	FooDB	DTU Food
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Octopus vulgaris	FooDB	DTU Food
Oenothera biennis	LOTUS Database	35616633
Olea europaea	FooDB	DTU Food
Oncorhynchus mykiss	FooDB	DTU Food
Opuntia	FooDB	DTU Food
Oryza sativa	FooDB	DTU Food
Ovis aries	FooDB	DTU Food
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Passiflora edulis	FooDB	DTU Food
Pastinaca sativa	FooDB	DTU Food
Perciformes	FooDB	DTU Food
Persea americana	FooDB	DTU Food
Petroselinum crispum	FooDB	DTU Food
Phaseolus vulgaris	FooDB	DTU Food
Phoenix dactylifera	FooDB	DTU Food
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Pinus	FooDB	DTU Food
Piper nigrum L.	FooDB	DTU Food
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	DTU Food
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Primula alpicola	LOTUS Database	35616633
Prunus armeniaca	FooDB	DTU Food
Prunus avium L.	FooDB	DTU Food
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	DTU Food
Prunus persica	FooDB	DTU Food
Prunus persica var. nucipersica	FooDB	DTU Food
Psidium guajava	FooDB	DTU Food
Punica granatum	FooDB	DTU Food
Pyrus communis	FooDB	DTU Food
Ranidae	FooDB	DTU Food
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes rubrum	FooDB	DTU Food
Ribes uva-crispa	FooDB	DTU Food
Rosa	FooDB	DTU Food
Rumex acetosa	FooDB	DTU Food
Saccharina japonica	FooDB	DTU Food
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	DTU Food
Sechium edule	FooDB	DTU Food
Sesamum indicum	FooDB	DTU Food
Siluriformes	FooDB	DTU Food
Solanum lycopersicum	FooDB	DTU Food
Solanum melongena	FooDB	DTU Food
Solanum tuberosum	FooDB	DTU Food
Spinacia oleracea	FooDB	DTU Food
Squalus acanthias	FooDB	DTU Food
Sus scrofa domestica	FooDB	DTU Food
Tamarindus indica	FooDB	DTU Food
Taraxacum officinale	FooDB	DTU Food
Thunnus	FooDB	DTU Food
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum durum	FooDB	DTU Food
Ulva fasciata	LOTUS Database	35616633
Undaria pinnatifida	LOTUS Database	35616633
Vaccinium	FooDB	DTU Food
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium vitis-idaea	FooDB	DTU Food
Vigna angularis	FooDB	DTU Food
Vigna radiata	FooDB	DTU Food
Vitis	FooDB	DTU Food
Zea mays L.	FooDB	DTU Food
Zingiber officinale	FooDB	DTU Food

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

long-chain fatty acid (CHEBI:32389 )
omega-3 fatty acid (CHEBI:32389 )
octadecatetraenoic acid (CHEBI:32389 )
Polyunsaturated fatty acids (C16300 )
Unsaturated fatty acids (LMFA01030357 )

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	6.19	ALOGPS
logP	5.7	ChemAxon
logS	-5.7	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	12	ChemAxon
Refractivity	90.75 m³·mol⁻¹	ChemAxon
Polarizability	33.11 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

HMDB0006547

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

5312508

PDB ID

Not Available

ChEBI ID

32389

Good Scents ID

Not Available

References

General References

Surette ME, Edens M, Chilton FH, Tramposch KM: Dietary echium oil increases plasma and neutrophil long-chain (n-3) fatty acids and lowers serum triacylglycerols in hypertriglyceridemic humans. J Nutr. 2004 Jun;134(6):1406-11. doi: 10.1093/jn/134.6.1406. [PubMed:15173404 ]
Miles EA, Banerjee T, Calder PC: The influence of different combinations of gamma-linolenic, stearidonic and eicosapentaenoic acids on the fatty acid composition of blood lipids and mononuclear cells in human volunteers. Prostaglandins Leukot Essent Fatty Acids. 2004 Jun;70(6):529-38. doi: 10.1016/j.plefa.2003.11.008. [PubMed:15120716 ]
Kimura K, Kamisaka Y, Uemura H, Yamaoka M: Increase in stearidonic acid by increasing the supply of histidine to oleaginous Saccharomyces cerevisiae. J Biosci Bioeng. 2014 Jan;117(1):53-6. doi: 10.1016/j.jbiosc.2013.06.004. Epub 2013 Aug 6. [PubMed:23932357 ]
Kuhnt K, Fuhrmann C, Kohler M, Kiehntopf M, Jahreis G: Dietary echium oil increases long-chain n-3 PUFAs, including docosapentaenoic acid, in blood fractions and alters biochemical markers for cardiovascular disease independently of age, sex, and metabolic syndrome. J Nutr. 2014 Apr;144(4):447-60. doi: 10.3945/jn.113.180802. Epub 2014 Feb 19. [PubMed:24553695 ]

Showing NP-Card for Stearidonic acid (NP0045037)

MOL for NP0045037 (Stearidonic acid)

3D MOL for NP0045037 (Stearidonic acid)

3D SDF for NP0045037 (Stearidonic acid)

3D-SDF for NP0045037 (Stearidonic acid)

PDB for NP0045037 (Stearidonic acid)

3D PDB for NP0045037 (Stearidonic acid)

SMILES for NP0045037 (Stearidonic acid)

INCHI for NP0045037 (Stearidonic acid)

Structure for NP0045037 (Stearidonic acid)

3D Structure for NP0045037 (Stearidonic acid)