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Showing Compound Arachidonic acid (FDB011872)

Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2025-11-18 23:31:47 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. Based on a literature review a significant number of articles have been published on Arachidonic acid.
CAS Number506-32-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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-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
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeledMeSH
Arachidonic acid, zinc salt, (all-Z)-isomerMeSH
Sodium arachidonateMeSH
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
(all-Z)-5,8,11,14-Eicosatetraenoic acidMeSH
Arachidonic acid, potassium salt, (all-Z)-isomerMeSH
(all-Z)-5,8,11,14-EicosatetraenoateHMDB
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
FA(20:4(5Z,8Z,11Z,14Z))HMDB
FA(20:4n6)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
cis-δ(5,8,11,14)-eicosatetraenoateGenerator
cis-δ(5,8,11,14)-eicosatetraenoic acidGenerator
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
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
5-alpha-reductase inhibitor50781 An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing prostate size, promoting hair growth, and minimizing sebaceous gland activity.DUKE
Anti dermatitic50177 An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.DUKE
Anti eczemic52217 An agent that reduces inflammation and itching, commonly used to manage eczema symptoms, atopic dermatitis, and other skin allergies, providing relief and preventing flare-ups.DUKE
Anti leukotriene-B435222 An agent that inhibits leukotriene B4, reducing inflammation and immune responses. It has therapeutic applications in managing inflammatory diseases, such as asthma and arthritis, by blocking leukotriene B4's role in attracting white blood cells to sites of inflammation. Key medical uses include treating respiratory and autoimmune disorders.DUKE
Anti-psoriatic52217 An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by modulating the immune system and inhibiting keratinocyte proliferation.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CoagulantAn agent that causes blood or another liquid to coagulate, playing a crucial biological role in wound healing and hemostasis. Therapeutically, coagulants are used to treat bleeding disorders, such as hemophilia, and to prevent excessive bleeding during surgery, with key medical uses including trauma treatment and transfusion medicine.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
InsulinogenicAn agent that stimulates insulin production and release by the pancreas, used therapeutically to manage diabetes and impaired glucose tolerance, and medically to treat conditions like hypoglycemia and insulin resistance.DUKE
MyocontractantAn agent that stimulates contractions of smooth muscle, playing a biological role in regulating muscle tone. Therapeutically, it has applications in treating conditions like uterine atony and gastrointestinal disorders. Key medical uses include inducing labor, managing postpartum hemorrhage, and treating gastrointestinal motility issues.DUKE
PyrogenicAn agent that induces fever, stimulating the immune system. It plays a biological role in fighting infection and has therapeutic applications in immunotherapy and vaccine development. Key medical uses include treating certain infections and cancers, as well as stimulating the immune system in immunocompromised patients.DUKE
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.