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Arachidonic acid (FDB011872)

Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2019-11-26 03:05:38 UTC
Primary IDFDB011872
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number506-32-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSArachidonic acid, 1 TMS, GC-MS Spectrumsplash10-005c-9800000000-87c290971fc8a628fb23Spectrum
GC-MSArachidonic acid, non-derivatized, GC-MS Spectrumsplash10-005c-9800000000-87c290971fc8a628fb23Spectrum
GC-MSArachidonic acid, non-derivatized, GC-MS Spectrumsplash10-0006-6900000000-6870df266b6c73f2a4a1Spectrum
Predicted GC-MSArachidonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7390000000-7004b9cd28a9b3d9c991Spectrum
Predicted GC-MSArachidonic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i9-9252000000-475d13959ee8ce889646Spectrum
Predicted GC-MSArachidonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSArachidonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0nmi-0913000000-95846e8d5e8afd29664b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-6bd9d0477c122d3eed942017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-510ea33e558fa238a1d22017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0009000000-73a6b21464acba15463c2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0049000000-102d050109d3c78b1a252017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0090000000-2fb9003e782ec3d05e202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0nmi-0913000000-95846e8d5e8afd29664b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-6bd9d0477c122d3eed942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-510ea33e558fa238a1d22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0049000000-102d050109d3c78b1a252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-6bd9d0477c122d3eed942021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-510ea33e558fa238a1d22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-1934000000-3fb5938d1b4795217a972021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-a42ea66033eb9771d36d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-5691000000-2bc7b1ae5487233dfce82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-7950000000-b15a8d382a4b3ad62d082017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-28a9bbfed5fabd10c0c22017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-3f6e64ef7522a793e9a92017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c72017-07-26View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH 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.