Adrenic acidDTA

PUFA22:4Ω-6

  Overview

Stats

PUFA
Type
22
Carbons
4
Double bonds
3
Bis-allylic sites
332.5
Weight · g/mol
—
Melting point
C22H36O2
Formula

Also known as

IUPAC (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
Systematic Docosatetraenoic acid

  At a Glance

Key Points

Also called adrenic acid; a 22-carbon omega-6 fat concentrated in the adrenal glands and brain.

Source

Found in meat. Also made by the body.

Type

Very-long-chain polyunsaturated fatty acid with 22 carbons and four cis double bonds, an omega-6 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Adrenic acid
IUPAC Name (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030178
Lipid Bank DFA0217
Swiss Lipids 000001124
PlantFA ID —
Food & Nutrition
FooDB FDB022918
INFOODS —
Chemistry / Compounds
PubChem CID 5497181
CAS 28874-58-0
ChEBI 53487
ChEMBL CHEMBL1491103
ChemSpider 4593749
InChIKey —
ZINC ID ZINC000004543724
NIKKAJI ID J13.758H
PDBe —
UCI (UniChem) 1002008
SureChEMBL 19452
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0002226
METLIN 6560
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1115
BioCyc/MetaCyc —
MetaNetX ID MNXM723041
BiGG ID 2218009
KEGG C16527
KNApSAcK C00052186
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs —
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) 64F675W6EN
FDA SRS (USA) 64F675W6EN
NHPID (Canada) —
DTXSID (USA) —
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-941-054
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 22:4 (2)

Other fatty acids sharing the 22:4 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Adrenic acid
(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
 7Z,10Z,13Z,16Z —
5497181
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
Positional (1)
4Z,7Z,10Z,13Z-Docosatetraenoic Acid
(4Z,7Z,10Z,13Z)-docosa-4,7,10,13-tetraenoic acid
 4Z,7Z,10Z,13Z —
5282843
Category Omega-9 Very Long-Chain Polyunsaturated Fatty Acid (EFAD Marker)
Conjugation Type Isolated
SMILES CCCCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)O
Description A 22-carbon omega-9 polyunsaturated fatty acid that accumulates during severe essential fatty acid deficiency, generated by elongation and Δ4 desaturation of Mead acid intermediates.
Origin Details
Origin Source Type Details
Endogenous Compensatory Synthesis Natural Produced from 7Z,10Z,13Z-docosatrienoic acid (22:3 n-9) via Δ4 desaturation in the Sprecher pathway, active only under sustained essential fatty acid deficiency.

Chemical Properties

Name(s):
Common Name Adrenic acid
Abbreviation DTA
Simple Notation 22:4
Notation 22:4(n-6)
IUPAC Name (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
Semi-systematic Docosatetraenoic acid
Structure:
Molecular C22H36O2
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
Cis / Trans cis
E-Z 7Z,10Z,13Z,16Z
Physical:
Weight 332.5 g/mol
Reactivity
Double Bonds 4
Bis-Allylic Carbons 3 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 10
ATP Yield (Net) 142 ATP