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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2022-03-07 02:49:13 UTC
HMDB IDHMDB0002226
Secondary Accession Numbers
  • HMDB0062580
  • HMDB02226
  • HMDB62580
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
Data?1582752237
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
7,10,13,16-DocosatetraenoateGenerator
7Z,10Z,13Z,16Z-DocosatetraenoateGenerator
all-cis-7,10,13,16-DocosatetraenoateGenerator
AdrenateGenerator
Adrenic acid, (Z)-isomerHMDB
7,10,13,16-Docosatetraenoic acid (van) adrenateHMDB
7,10,13,16-Docosatetraenoic acid (van) adrenic acidHMDB
FA(22:4(7Z,10Z,13Z,16Z))HMDB
(7Z,10Z,13Z,16Z)-DocosatetraenoateHMDB
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
Description 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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker190.92130932474
[M+H]+Baker189.41330932474
[M-H]-Not Available190.921http://allccs.zhulab.cn/database/detail?ID=AllCCS00001853
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.60431661259
DarkChem[M-H]-196.9431661259
DeepCCS[M+H]+193.85330932474
DeepCCS[M-H]-191.49630932474
DeepCCS[M-2H]-224.38230932474
DeepCCS[M+Na]+199.94730932474
AllCCS[M+H]+191.632859911
AllCCS[M+H-H2O]+188.832859911
AllCCS[M+NH4]+194.132859911
AllCCS[M+Na]+194.932859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-194.032859911
AllCCS[M+HCOO]-196.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Adrenic acidCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O3822.9Standard polar33892256
Adrenic acidCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O2318.1Standard non polar33892256
Adrenic acidCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O2517.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adrenic acid,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C2569.4Semi standard non polar33892256
Adrenic acid,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C(C)(C)C2816.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Adrenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0036-6190000000-01004b4dbd386205a17a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adrenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9363000000-8f2004351a750c8ae6282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adrenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Adrenic acid 35V, Negative-QTOFsplash10-0019-0094000000-df4348e7bc0ef4daa7932021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 10V, Negative-QTOFsplash10-001i-0019000000-22bd8471322b5ca375e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 20V, Negative-QTOFsplash10-01qi-1039000000-e56955cf18df0497d9a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 40V, Negative-QTOFsplash10-0a4l-9140000000-046f31ddb29054b154e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 10V, Negative-QTOFsplash10-001i-0009000000-8720d4badc25c6c95dce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 20V, Negative-QTOFsplash10-01q9-1009000000-d05f8cd009c170badacf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 40V, Negative-QTOFsplash10-0006-9111000000-85f143e78a3bcd8b33e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 10V, Positive-QTOFsplash10-014i-0039000000-abc8b24aa60e4616175b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 20V, Positive-QTOFsplash10-00yr-4493000000-120f43f1783f4df082962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 40V, Positive-QTOFsplash10-0597-8960000000-43890a474588aa5b958c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 10V, Positive-QTOFsplash10-00lr-2229000000-84779d8a6e57c8c625ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 20V, Positive-QTOFsplash10-00lr-8934000000-cfe052bf7962eec8453b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adrenic acid 40V, Positive-QTOFsplash10-05o3-9400000000-052c317a4ec4bc2b67432021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Neuron
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.657 +/- 3.137 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.01 +/- 0.48 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified16.1 +/- 6.5 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not QuantifiedNot QuantifiedNewborn (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
FooDB IDFDB022918
KNApSAcK IDC00052186
Chemspider ID4593749
KEGG Compound IDC16527
BioCyc IDNot Available
BiGG ID2218009
Wikipedia LinkAdrenic acid
METLIN ID6560
PubChem Compound5497181
PDB IDNot Available
ChEBI ID53487
Food Biomarker OntologyNot Available
VMH IDADRN
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.