Adrenic acid (CHEM035380)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:42:57 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035380
Identification
Common NameAdrenic acid
ClassSmall Molecule
DescriptionAdrenic acid, also known as adrenate, 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. Adrenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Adrenic acid participates in a number of enzymatic reactions, within cattle. In particular, Adrenic acid can be biosynthesized from arachidonic acid through its interaction with the enzyme elongation OF very long chain fatty acids protein 5. In addition, Adrenic acid can be converted into tetracosatetraenoic acid (24:4N-6); which is mediated by the enzyme elongation OF very long chain fatty acids protein 4. In cattle, adrenic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AdrenateGenerator
Adrenic acid, (Z)-isomerMeSH
7,10,13,16-Docosatetraenoic acidMeSH
Adrenic acidMeSH
Chemical FormulaC22H36O2
Average Molecular Mass332.528 g/mol
Monoisotopic Mass332.272 g/mol
CAS Registry Number28874-58-0
IUPAC Name(7E,10E,13E,16E)-docosa-7,10,13,16-tetraenoic acid
Traditional Nameadrenate
SMILES[H]\C(CCCCC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCC(O)=O
InChI IdentifierInChI=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-CGRWFSSPSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability41.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-abc8b24aa60e4616175bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yr-4493000000-019f12e2bcc48efd774fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0597-8960000000-d3ae0a0134f32f4b2888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-22bd8471322b5ca375e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-1039000000-e56955cf18df0497d9a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-046f31ddb29054b154e8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDocosatetraenoic acid
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5282844
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.
2. 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