Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2018-05-28 23:32:11 UTC
Primary IDFDB011872
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArachidonic acid
DescriptionEssential fatty acid. Constituent of many animal phospholipids Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(omega-6). It is the counterpart to the saturated arachidic acid found in peanut oil, (L. arachis – peanut.) .
CAS Number506-32-1
Structure
Thumb
Synonyms
SynonymSource
(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)-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
(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
5Z,8Z,11Z,14Z-EicosatetraenoateHMDB
5Z,8Z,11Z,14Z-Eicosatetraenoic acidHMDB
cis-D5,8,11,14-EicosatetraenoateHMDB
cis-D5,8,11,14-Eicosatetraenoic acidHMDB
ImmunocytophyteHMDB
Arachidonate, sodiumMeSH
Arachidonic acid, (all-Z)-isomer, 3H-labeledMeSH
Arachidonic acid, ammonium salt, (all-Z)-isomerMeSH
Arachidonic acid, cerium salt, (all-Z)-isomerMeSH
Arachidonic acid, sodium saltMeSH
Arachidonic acid, sodium salt, (all-Z)-isomerMeSH
Vitamin FMeSH
Arachidonic acid, cesium salt, (all-Z)-isomerMeSH
Arachidonic acid, lithium salt, (all-Z)-isomerMeSH
Arachidonic acid, potassium salt, (all-Z)-isomerMeSH
Sodium arachidonateMeSH
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeledMeSH
Arachidonic acid, zinc salt, (all-Z)-isomerMeSH
FA(20:4(5Z,8Z,11Z,14Z))HMDB
5,8,11,14-Eicosatetraenoic acid, (all-Z)-biospider
Arachidonic aciddb_source
cis-5,8,11,14-eicosatetraenoic acidbiospider
cis-delta-5,8,11,14-eicosatetraenoic acidmanual
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H32O2
IUPAC name(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
InChI IdentifierInChI=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
Isomeric SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointMp -49.5°DFC
Boiling PointBp1 163°DFC
Experimental Water SolubilityNot Available
Experimental logP6.98SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge-1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-87c290971fc8a628fb23View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-87c290971fc8a628fb23View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-6900000000-6870df266b6c73f2a4a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7390000000-7004b9cd28a9b3d9c991View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-9252000000-475d13959ee8ce889646View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0nmi-0913000000-95846e8d5e8afd29664bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-6bd9d0477c122d3eed94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-510ea33e558fa238a1d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0009000000-73a6b21464acba15463cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0049000000-102d050109d3c78b1a25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0090000000-2fb9003e782ec3d05e20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0nmi-0913000000-95846e8d5e8afd29664bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-6bd9d0477c122d3eed94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-510ea33e558fa238a1d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0049000000-102d050109d3c78b1a25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-a42ea66033eb9771d36dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-5691000000-2bc7b1ae5487233dfce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-7950000000-b15a8d382a4b3ad62d08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-28a9bbfed5fabd10c0c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-3f6e64ef7522a793e9a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c7View in MoNA
ChemSpider ID392692
ChEMBL IDCHEMBL15594
KEGG Compound IDC00219
Pubchem Compound ID444899
Pubchem Substance IDNot Available
ChEBI ID15843
Phenol-Explorer IDNot Available
DrugBank IDDB04557
HMDB IDHMDB60102
CRC / DFC (Dictionary of Food Compounds) IDHBJ66-U:HBJ63-R
EAFUS IDNot Available
Dr. Duke IDARACHIDONIC-ACID
BIGG ID1586189
KNApSAcK IDC00000388
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArachidonic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukotriene-B435222 A substance that diminishes the rate of a chemical reaction.DUKE
anti psoriatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
coagulantDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
insulinogenicDUKE
myocontractantDUKE
pyrogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.