NP-MRD: Showing NP-Card for sciadonic acid (NP0235022)

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Record Information

Version

2.0

Created at

2022-09-06 17:25:05 UTC

Updated at

2022-09-06 17:25:05 UTC

NP-MRD ID

NP0235022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sciadonic acid

Description

Sciadonic acid, also known as C20:3N-6,9,15 or sciadonate, 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. sciadonic acid is found in Juniperus phoenicea, Nageia nagi and Platycladus orientalis. sciadonic acid was first documented in 2001 (PMID: 11559362). Sciadonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 17384161) (PMID: 19270392) (PMID: 22178003) (PMID: 22889893).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 56 55  0  0  0  0  0  0  0  0999 V2000
    8.1997    2.4585   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6806    2.1691    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6128    0.7242    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3843    0.0430    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1851   -0.0170   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276    1.2466   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.6566   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906    0.9826    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -0.3351    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520   -1.3962    0.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562   -1.4750   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -1.9694    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483   -2.0593   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9396   -2.5493    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4062   -1.6444    1.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5855   -1.0684    1.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5975   -1.2071    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9731    0.0593   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    0.7846   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8004    1.3561   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5715    1.4353    0.7141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7828    1.9205   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4467    2.2269   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3584    3.5384    0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7920    1.8607    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1953    2.3863   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3978    2.8552    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1114    0.2039   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3998    0.5242    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0802    0.3928    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6906   -1.0436    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -0.8741    0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5559   -0.3686   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    1.9792   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    2.6897   -0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    1.0295    0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    1.6535    1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -0.4503    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271   -2.3421    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0350   -2.2909   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -0.5674   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3642   -2.9903    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7955   -1.3183    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183   -1.0738   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704   -2.8024   -1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6516   -2.6615   -0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087   -3.5343    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -1.4147    2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8670   -0.4090    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5775   -1.5337    0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4158   -1.9947   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4491    0.7715    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8396   -0.2170   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4488    1.6506   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5539    0.1691   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    2.8402   -1.7187 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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END


  Mrv1652312251820292D          

 22 21  0  0  0  0            999 V2000
10006.483610007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.198910007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.916310007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.630210007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.455410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.169910007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.884510007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.709710007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.424210007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.138810007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.853210007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.568010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.282510007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.770310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.054910007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.230310007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.515010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.801710007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.086410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.371010007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.657710007.3668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.371010008.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0235022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/CCCC\C=C/CCCC(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/h6-7,9-10,15-16H,2-5,8,11-14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,16-15-

> <INCHI_KEY>
PRHHYVQTPBEDFE-URZBRJKDSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.49

> <EXACT_MASS>
306.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.57703994271556

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,11Z,14Z)-icosa-5,11,14-trienoic acid

> <ALOGPS_LOGP>
7.26

> <JCHEM_LOGP>
6.9490924676666666

> <ALOGPS_LOGS>
-6.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885676019177561

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
98.83739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.62e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sciadonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-DEC-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-DEC-18         0                                  
HETATM    1  C   UNK     0    8678.7698681.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8680.1058680.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8681.4448681.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8682.7768680.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8684.3178680.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8685.6508681.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8686.9848680.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8688.5258680.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8689.8598681.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8691.1928680.418   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8692.5268681.188   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8693.8608680.418   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8695.1948681.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8677.4388680.418   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8676.1038681.188   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8674.5638681.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8673.2288680.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8671.8978681.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.5618680.418   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.2268681.188   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8667.8948680.418   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8669.2268682.726   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
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                                                            
CONECT   14    1   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                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
(5Z,11Z,14Z)-Eicosatrienoic acid	ChEBI
5Z,11Z,14Z-Eicosatrienoic acid	ChEBI
all-cis-5,11,14-Eicosatrienoic acid	ChEBI
all-cis-5,11,14-Icosatrienoic acid	ChEBI
C20:3N-6,9,15	ChEBI
(5Z,11Z,14Z)-Eicosatrienoate	Generator
5Z,11Z,14Z-Eicosatrienoate	Generator
all-cis-5,11,14-Eicosatrienoate	Generator
all-cis-5,11,14-Icosatrienoate	Generator
Sciadonate	Generator
5C,11C,14C-Eicosatrienoic acid	MeSH
Eicosa-5,11,14-trienoic acid	MeSH
5,11,14-Eicosatrienoic acid	MeSH
Icosa-5,11,14-trienoic acid	MeSH
Eicosa-5,11,14-trienoic acid, (Z,Z,Z)-isomer	MeSH
(5Z,11Z,14Z)-5,11,14-Eicosatrienoic acid	PhytoBank
(Z,Z,Z)-5,11,14-Eicosatrienoic acid	PhytoBank
cis,cis,cis-5,11,14-Eicosatrienoic acid	PhytoBank
cis-5,cis-11,cis-14-Eicosatrienoic acid	PhytoBank
Sciadonic acid	PhytoBank
FA(20:3(5Z,11Z,14Z))	PhytoBank

Chemical Formula

C₂₀H₃₄O₂

Average Mass

306.4900 Da

Monoisotopic Mass

306.25588 Da

IUPAC Name

(5Z,11Z,14Z)-icosa-5,11,14-trienoic acid

Traditional Name

sciadonic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCC\C=C/CCCC(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/h6-7,9-10,15-16H,2-5,8,11-14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,16-15-

InChI Key

PRHHYVQTPBEDFE-URZBRJKDSA-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
Juniperus phoenicea	LOTUS Database	35616633
Nageia nagi	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633

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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

icosatrienoic acid (CHEBI:82832 )
Unsaturated fatty acids (LMFA01030380 )

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	7.26	ALOGPS
logP	6.95	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.89	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	15	ChemAxon
Refractivity	98.84 m³·mol⁻¹	ChemAxon
Polarizability	38.58 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

445084

PDB ID

Not Available

ChEBI ID

82832

Good Scents ID

Not Available

References

General References

Tanaka T, Morishige J, Takimoto T, Takai Y, Satouchi K: Metabolic characterization of sciadonic acid (5c,11c,14c-eicosatrienoic acid) as an effective substitute for arachidonate of phosphatidylinositol. Eur J Biochem. 2001 Sep;268(18):4928-39. doi: 10.1046/j.0014-2956.2001.02423.x. [PubMed:11559362 ]
Sayanova O, Haslam R, Venegas Caleron M, Napier JA: Cloning and characterization of unusual fatty acid desaturases from Anemone leveillei: identification of an acyl-coenzyme A C20 Delta5-desaturase responsible for the synthesis of sciadonic acid. Plant Physiol. 2007 May;144(1):455-67. doi: 10.1104/pp.107.098202. Epub 2007 Mar 23. [PubMed:17384161 ]
Endo Y, Tsunokake K, Ikeda I: Effects of non-methylene-interrupted polyunsaturated fatty acid, sciadonic (all-cis-5,11,14-eicosatrienoic acid) on lipid metabolism in rats. Biosci Biotechnol Biochem. 2009 Mar 23;73(3):577-81. doi: 10.1271/bbb.80646. Epub 2009 Mar 7. [PubMed:19270392 ]
Ells R, Kock JL, Albertyn J, Hugo A, Pohl CH: Sciadonic acid modulates prostaglandin E2 production by epithelial cells during infection with C. albicans and C. dubliniensis. Prostaglandins Other Lipid Mediat. 2012 Jan;97(1-2):66-71. doi: 10.1016/j.prostaglandins.2011.12.001. Epub 2011 Dec 10. [PubMed:22178003 ]
Chen SJ, Huang WC, Yang TT, Lu JH, Chuang LT: Incorporation of sciadonic acid into cellular phospholipids reduces pro-inflammatory mediators in murine macrophages through NF-kappaB and MAPK signaling pathways. Food Chem Toxicol. 2012 Oct;50(10):3687-95. doi: 10.1016/j.fct.2012.07.057. Epub 2012 Aug 6. [PubMed:22889893 ]
LOTUS database [Link]

Showing NP-Card for sciadonic acid (NP0235022)

MOL for NP0235022 (sciadonic acid)

3D MOL for NP0235022 (sciadonic acid)

3D SDF for NP0235022 (sciadonic acid)

3D-SDF for NP0235022 (sciadonic acid)

PDB for NP0235022 (sciadonic acid)

3D PDB for NP0235022 (sciadonic acid)

SMILES for NP0235022 (sciadonic acid)

INCHI for NP0235022 (sciadonic acid)

Structure for NP0235022 (sciadonic acid)

3D Structure for NP0235022 (sciadonic acid)