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Showing NP-Card for Arachidonic acid (NP0047724)

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Record Information
Version2.0
Created at2022-03-17 20:44:54 UTC
Updated at2022-03-17 20:44:54 UTC
NP-MRD IDNP0047724
Secondary Accession NumbersNone
Natural Product Identification
Common NameArachidonic acid
DescriptionArachidonic acid, also known as arachidonate or AA, 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. Arachidonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Arachidonic acid exists in all living organisms, ranging from bacteria to humans. In humans, arachidonic acid is involved in mefenamic acid action pathway. Outside of the human body, Arachidonic acid is found, on average, in the highest concentration within a few different foods, such as coho salmons, milk (cow), and anchovies and in a lower concentration in meat bouillons, peachs, and salmonidae (salmon, trout). Arachidonic acid has also been detected, but not quantified in, several different foods, such as loquats, syrups, gins, cocoa butters, and garden cress. This could make arachidonic acid a potential biomarker for the consumption of these foods. Arachidonic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, gestational diabetes, schizophrenia, and bladder infections; arachidonic acid has also been linked to the inborn metabolic disorder isovaleric acidemia. Arachidonic acid is found in Abies pinsapo, Agaricus blazei, Aloe vera, Cystoclonium purpureum, Diplotaxis harra, Dipteryx lacunifera, Epilobium parviflorum, Eurhynchium striatum, Gossypium hirsutum, Homo sapiens (Serum), Leptomitus lacteus, Mnium spp., Mortierella alpina, Mus musculus, Nigella sativa, Picea jezoensis, Populus balsamifera, Portulaca oleracea, Ptilota filicina, Salvia fruticosa, Sarcophyton crassocaule, Sarcophyton trocheliophorum, Scolopendrium vulgare, Senna siamea, Serpocaulon loriceum, Stellaria dichotoma, Thuidium recognitum, Tornabea scutellifera, Trifolium pratense and Undaria pinnatifida. Arachidonic acid was first documented in 2003 (PMID: 14626496). A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14 (PMID: 16785341) (PMID: 16617398) (PMID: 14626494) (PMID: 12877651) (PMID: 15878913) (PMID: 15927922).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047724 (Arachidonic acid)


  Mrv1652303231821242D          

 22 21  0  0  0  0            999 V2000
   -1.2343    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4129    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6587    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6230   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3332    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0474   -0.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3332    0.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2258   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9359    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6501   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
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3D MOL for NP0047724 (Arachidonic acid)

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3D SDF for NP0047724 (Arachidonic acid)

  Mrv1652303231821242D          

 22 21  0  0  0  0            999 V2000
   -1.2343    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4129    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6587    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6230   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3332    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0474   -0.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3332    0.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2258   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9359    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6501   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047724

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
YZXBAPSDXZZRGB-DOFZRALJSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.4669

> <EXACT_MASS>
304.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.19605148359834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
6.80

> <JCHEM_LOGP>
6.587170811

> <ALOGPS_LOGS>
-6.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
99.95399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arachidonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047724 (Arachidonic acid)
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PDB for NP0047724 (Arachidonic acid)
HEADER    PROTEIN                                 23-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-18         0                                  
HETATM    1  C   UNK     0      -2.304   0.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.771   0.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.638  -0.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.563  -0.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.963   0.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.896   0.247   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.504   0.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.429   0.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.822  -0.524   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.762  -0.524   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.163   0.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.088   0.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.496  -0.524   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.629   0.247   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.822   0.247   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.963  -0.524   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.155  -0.524   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -11.822   1.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.288   0.247   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.622  -0.524   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.947   0.247   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.280  -0.524   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

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3D PDB for NP0047724 (Arachidonic acid)
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SMILES for NP0047724 (Arachidonic acid)
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
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INCHI for NP0047724 (Arachidonic acid)
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
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Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-Icosatetraenoic acidChEBI
AAChEBI
all-cis-5,8,11,14-Eicosatetraenoic acidChEBI
ARAChEBI
ArachidonateChEBI
ArachidonsaeureChEBI
cis-5,8,11,14-Eicosatetraenoic acidChEBI
cis-Delta(5,8,11,14)-Eicosatetraenoic acidChEBI
5Z,8Z,11Z,14Z-Eicosatetraenoic acidKegg
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acidKegg
(5Z,8Z,11Z,14Z)-5,8,11,14-IcosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-IcosatetraenoateGenerator
all-cis-5,8,11,14-EicosatetraenoateGenerator
cis-5,8,11,14-EicosatetraenoateGenerator
cis-delta(5,8,11,14)-EicosatetraenoateGenerator
cis-Δ(5,8,11,14)-eicosatetraenoateGenerator
cis-Δ(5,8,11,14)-eicosatetraenoic acidGenerator
5Z,8Z,11Z,14Z-EicosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoateGenerator
(all-Z)-5,8,11,14-EicosatetraenoateHMDB
(all-Z)-5,8,11,14-Eicosatetraenoic acidHMDB
5,8,11,14-all-cis-EicosatetraenoateHMDB
5,8,11,14-all-cis-Eicosatetraenoic acidHMDB
5,8,11,14-EicosatetraenoateHMDB
5,8,11,14-Eicosatetraenoic acidHMDB
5-cis,8-cis,11-cis,14-cis-EicosatetraenoateHMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acidHMDB
cis-D5,8,11,14-EicosatetraenoateHMDB
cis-D5,8,11,14-Eicosatetraenoic acidHMDB
ImmunocytophyteHMDB
Arachidonate, sodiumHMDB
Arachidonic acid, (all-Z)-isomer, 3H-labeledHMDB
Arachidonic acid, ammonium salt, (all-Z)-isomerHMDB
Arachidonic acid, cerium salt, (all-Z)-isomerHMDB
Arachidonic acid, sodium saltHMDB
Arachidonic acid, sodium salt, (all-Z)-isomerHMDB
Vitamin FHMDB
Arachidonic acid, cesium salt, (all-Z)-isomerHMDB
Arachidonic acid, lithium salt, (all-Z)-isomerHMDB
Arachidonic acid, potassium salt, (all-Z)-isomerHMDB
Sodium arachidonateHMDB
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeledHMDB
Arachidonic acid, zinc salt, (all-Z)-isomerHMDB
FA(20:4(5Z,8Z,11Z,14Z))HMDB
FA(20:4n6)HMDB
Chemical FormulaC20H32O2
Average Mass304.4669 Da
Monoisotopic Mass304.24023 Da
IUPAC Name(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional Namearachidonic acid
CAS Registry Number506-32-1
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChI KeyYZXBAPSDXZZRGB-DOFZRALJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abies pinsapoLOTUS Database
Abramis bramaFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
Agaricus blazeiLOTUS Database
Allium cepa L.FooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Aloe veraLOTUS Database
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Armoracia rusticanaFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Belone beloneFooDB
Bertholletia excelsaFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
BrachyuraFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. rapaFooDB
Bubalus bubalisFooDB
Cantharellus cibariusFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Carica papaya L.FooDB
CarideaFooDB
Carthamus tinctoriusFooDB
Carya illinoinensisFooDB
CastaneaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
ColumbaFooDB
ColumbidaeFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Cucumis meloFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cynara scolymusFooDB
Cystoclonium purpureumLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
DioscoreaFooDB
DiospyrosFooDB
Diplotaxis harraLOTUS Database
Dipteryx lacuniferaLOTUS Database
Dromaius novaehollandiaeFooDB
ElaeisFooDB
EngraulidaeFooDB
Epilobium parviflorumLOTUS Database
Equus caballusFooDB
Eriobotrya japonicaFooDB
Esox luciusFooDB
EucheumaFooDB
Eurhynchium striatumLOTUS Database
Fagopyrum esculentumFooDB
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
GastropodaFooDB
Glycine maxFooDB
GossypiumFooDB
Gossypium hirsutumLOTUS Database
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hippoglossus hippoglossusFooDB
Homo sapiens (Serum)Animalia
Hordeum vulgareFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans nigra L.FooDB
Lactuca sativaFooDB
Lagopus mutaFooDB
Lens culinarisFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Leptomitus lacteusLOTUS Database
Lepus timidusFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lota lotaFooDB
MalusFooDB
Malus pumilaFooDB
Mangifera indicaFooDB
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Medicago sativaFooDB
Melanitta fuscaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Merlangius merlangusFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Mnium spp.-
Molva molvaFooDB
Mortierella alpinaFungi
Mus musculusLOTUS Database
Musa x paradisiacaFooDB
Myristica fragransFooDB
MytilidaeFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Nigella sativaLOTUS Database
Numida meleagrisFooDB
Octopus vulgarisFooDB
OdocoileusFooDB
Olea europaeaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
OpuntiaFooDB
OryctolagusFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PerciformesFooDB
Persea americanaFooDB
Petroselinum crispumFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Picea jezoensisLOTUS Database
PinusFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Populus balsamiferaLOTUS Database
Portulaca oleraceaLOTUS Database
Prunus armeniacaFooDB
Prunus avium L.FooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Psidium guajavaFooDB
Ptilota filicina-
Punica granatumFooDB
Pyrus communisFooDB
RanidaeFooDB
Raphanus sativus var. longipinnatusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rumex acetosaFooDB
Saccharina japonicaFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia fruticosaLOTUS Database
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Sarcophyton crassocauleLOTUS Database
Sarcophyton trocheliophorumLOTUS Database
Scolopendrium vulgare-
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Senna siameaLOTUS Database
Serpocaulon loriceumLOTUS Database
Sesamum indicumFooDB
SiluriformesFooDB
Solanum lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumFooDB
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Stellaria dichotomaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Thuidium recognitumLOTUS Database
ThunnusFooDB
Tornabea scutelliferaLOTUS Database
Trifolium pratenseLOTUS Database
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum durumFooDB
Undaria pinnatifidaLOTUS Database
VacciniumFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
Vigna angularisFooDB
Vigna radiataFooDB
VitisFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentLong-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.8ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m³·mol⁻¹ChemAxon
Polarizability37.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001043  
DrugBank IDDB04557  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011872  
KNApSAcK IDC00000388  
Chemspider ID392692  
KEGG Compound IDC00219  
BioCyc IDARACHIDONIC_ACID  
BiGG ID1586189  
Wikipedia LinkArachidonic_acid  
METLIN ID193  
PubChem Compound444899  
PDB IDNot Available
ChEBI ID15843  
Good Scents IDNot Available
References
General References
  1. Frelinger AL 3rd, Furman MI, Linden MD, Li Y, Fox ML, Barnard MR, Michelson AD: Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance. Circulation. 2006 Jun 27;113(25):2888-96. Epub 2006 Jun 19. [PubMed:16785341  ] 
  2. Daskalou T, Karamouzis M, Liaros G: [Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques]. Hell J Nucl Med. 2006 Jan-Apr;9(1):49-52. [PubMed:16617398  ] 
  3. Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71. doi: 10.1016/s1098-8823(03)00077-7. [PubMed:14626496  ] 
  4. Claria J, Arroyo V: Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):19-33. doi: 10.1016/s1098-8823(03)00075-3. [PubMed:14626494  ] 
  5. Pantaleo P, Marra F, Vizzutti F, Spadoni S, Ciabattoni G, Galli C, La Villa G, Gentilini P, Laffi G: Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis. Clin Sci (Lond). 2004 Jan;106(1):27-34. doi: 10.1042/CS20030182. [PubMed:12877651  ] 
  6. Hughes-Fulford M, Tjandrawinata RR, Li CF, Sayyah S: Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells. Carcinogenesis. 2005 Sep;26(9):1520-6. doi: 10.1093/carcin/bgi112. Epub 2005 May  5. [PubMed:15878913  ] 
  7. Kudolo GB, Wang W, Barrientos J, Elrod R, Blodgett J: The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers. J Herb Pharmacother. 2004;4(4):13-26. [PubMed:15927922  ] 
  8. Burke J, Kraft WK, Greenberg HE, Gleave M, Pitari GM, VanBuren S, Wagner JA, Waldman SA: Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation. J Clin Pharmacol. 2003 Sep;43(9):983-9. doi: 10.1177/0091270003257216. [PubMed:12971030  ]