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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2018-05-20 09:41:13 UTC
HMDB IDHMDB0002226
Secondary Accession Numbers
  • HMDB02226
Metabolite Identification
Common NameAdrenic acid
DescriptionAdrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Adrenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Adrenic acid can be found in blood and in human myelin tissue. Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome. It can also be found in the extracellular space. In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid. In particular, all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the trivial name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs) (Wikipedia). Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent (PMID: 1642692 ).
Structure
Thumb
Synonyms
ValueSource
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acidChEBI
7,10,13,16-Docosatetraenoic acidChEBI
7Z,10Z,13Z,16Z-Docosatetraenoic acidChEBI
all-cis-7,10,13,16-Docosatetraenoic acidChEBI
cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeureChEBI
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoateGenerator
AdrenateGenerator
7,10,13,16-DocosatetraenoateGenerator
7Z,10Z,13Z,16Z-DocosatetraenoateGenerator
all-cis-7,10,13,16-DocosatetraenoateGenerator
7,10,13,16-Docosatetraenoic acid (van) adrenateHMDB
7,10,13,16-Docosatetraenoic acid (van) adrenic acidHMDB
Adrenic acid, (Z)-isomerMeSH
FA(22:4(7Z,10Z,13Z,16Z))HMDB
Chemical FormulaC22H36O2
Average Molecular Weight332.52
Monoisotopic Molecular Weight332.271530396
IUPAC Name(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
Traditional Namedocosatetraenoic acid
CAS Registry Number28874-58-0
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
InChI Identifier
InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-
InChI KeyTWSWSIQAPQLDBP-DOFZRALJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8e-05 g/LALOGPS
logP7.42ALOGPS
logP7.48ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity109.16 m³·mol⁻¹ChemAxon
Polarizability41.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0036-6190000000-01004b4dbd386205a17aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9363000000-8f2004351a750c8ae628View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-abc8b24aa60e4616175bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yr-4493000000-120f43f1783f4df08296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0597-8960000000-43890a474588aa5b958cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-22bd8471322b5ca375e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-1039000000-e56955cf18df0497d9a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-046f31ddb29054b154e8View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Myelin
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.01 +/- 0.48 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.417 +/- 0.070 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.364 +/- 0.005 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified14.5 +/- 4.6 uMAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified16.1 +/- 6.5 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease References
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022918
KNApSAcK IDNot Available
Chemspider ID4593749
KEGG Compound IDC16527
BioCyc IDNot Available
BiGG ID2218009
Wikipedia LinkDocosatetraenoic acid
METLIN ID6560
PubChem Compound5497181
PDB IDNot Available
ChEBI ID53487
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Martinez M, Mougan I: Fatty acid composition of brain glycerophospholipids in peroxisomal disorders. Lipids. 1999 Jul;34(7):733-40. [PubMed:10478932 ]
  2. Ren H, Magulike N, Ghebremeskel K, Crawford M: Primary open-angle glaucoma patients have reduced levels of blood docosahexaenoic and eicosapentaenoic acids. Prostaglandins Leukot Essent Fatty Acids. 2006 Mar;74(3):157-63. Epub 2006 Jan 10. [PubMed:16410047 ]
  3. Tardy B, Bordet JC, Berruyer M, Ffrench P, Dechavanne M: Priming effect of adrenic acid (22:4(n-6)) on tissue factor activity expressed by thrombin-stimulated endothelial cells. Atherosclerosis. 1992 Jul;95(1):51-8. [PubMed:1642692 ]