Showing metabocard for Arachidonic acid (BMDB0001043)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:16 UTC
Update Date2020-06-04 21:12:18 UTC
MCDB ID BMDB0001043
Secondary Accession Numbers
  • BMDB0060102
  • BMDB01043
  • BMDB60102
Metabolite 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. Arachidonic acid has been found to be associated with several diseases known as colorectal cancer, hypertension, bladder infections, and gestational diabetes; also arachidonic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
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
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
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.98SANGSTER (1993)
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-87c290971fc8a628fb232014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-87c290971fc8a628fb232017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-6900000000-6870df266b6c73f2a4a12017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7390000000-7004b9cd28a9b3d9c9912017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-9252000000-475d13959ee8ce8896462017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0nmi-0913000000-95846e8d5e8afd29664b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-6bd9d0477c122d3eed942017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-510ea33e558fa238a1d22017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0009000000-73a6b21464acba15463c2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0049000000-102d050109d3c78b1a252017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0090000000-2fb9003e782ec3d05e202017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0nmi-0913000000-95846e8d5e8afd29664b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-6bd9d0477c122d3eed942017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-510ea33e558fa238a1d22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0049000000-102d050109d3c78b1a252017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-6bd9d0477c122d3eed942021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-510ea33e558fa238a1d22021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-1934000000-3fb5938d1b4795217a972021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-a42ea66033eb9771d36d2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-5691000000-2bc7b1ae5487233dfce82017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-7950000000-b15a8d382a4b3ad62d082017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-28a9bbfed5fabd10c0c22017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-3f6e64ef7522a793e9a92017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c72017-07-26View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified1116 +/- 459 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified2595 +/- 624 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified2463 +/- 525 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified952 +/- 328 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified657 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified1313 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
Detected and Quantified1642 uMTotal fatty acid
  • M.J. Abarghuei, Y...
 details
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
References
Synthesis ReferenceDai, Chuanchao; Yuan, Zhilin; Wang, Anqi. Production of arachidonic acid and eicosapentaenoic acid with organic wastewater of soybean products. Zhongguo Youzhi (2004), 29(5), 31-33.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  4. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
  5. M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.