ChemFOnt: Showing chemical card for Hexacosaenoic acid (CFc000333376)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:24 UTC

Chemfont ID

CFc000333376

Molecule Identification

Common Name

Hexacosaenoic acid

Definition

Hexacosanoic acid, also known as N-hexacosanoate or c26:0, 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. Thus, hexacosanoic acid is considered to be a fatty acid lipid molecule. Hexacosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Hexacosanoic acid can be found in a number of food items such as dandelion, potato, cottonseed, and sugar apple, which makes hexacosanoic acid a potential biomarker for the consumption of these food products. Hexacosanoic acid can be found primarily in blood, as well as in human adrenal gland and fibroblasts tissues. Hexacosanoic acid exists in all eukaryotes, ranging from yeast to humans. In humans, hexacosanoic acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Hexacosanoic acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Moreover, hexacosanoic acid is found to be associated with adrenomyeloneuropathy, peroxisomal biogenesis defect, and adrenoleukodystrophy, neonatal. Hexacosanoic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. [In the chem box it is shown folded only because of lack of space. In fact, it is a straight-chain, saturated fatty acid.] . Treatment options for adrenoleukodystrophy (ALD) are limited. Dietary treatment is with Lorenzo's oil. For the childhood cerebral form, stem cell transplant and gene therapy are options if the disease is detected early in the clinical course. Adrenal insufficiency in ALD patients can be successfully treated (T3DB).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C26:0	ChEBI
Ceratinic acid	ChEBI
Ceric acid	ChEBI
Cerinic acid	ChEBI
Cerotic acid	ChEBI
Cerotinic acid	ChEBI
Cerylic acid	ChEBI
CH3-[CH2]24-COOH	ChEBI
Hexacosansaeure	ChEBI
Hexacosoic acid	ChEBI
Hexaeicosanoic acid	ChEBI
N-C26:0	ChEBI
N-Hexacosanoic acid	ChEBI
Ceratinate	Generator
Cerate	Generator
Cerinate	Generator
Cerotate	Generator
Cerotinate	Generator
Cerylate	Generator
Hexacosoate	Generator
Hexaeicosanoate	Generator
N-Hexacosanoate	Generator
Hexacosanoate	Generator
Hexacosanoate (N-C26:0)	HMDB
Hexacosanoic acid	PhytoBank
FA(26:0)	PhytoBank

Chemical Formula

C₂₆H₅₂O₂

Average Molecular Weight

396.6899

Monoisotopic Molecular Weight

396.396730908

IUPAC Name

hexacosanoic acid

Traditional Name

hexacosanoic acid

CAS Registry Number

506-46-7

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C26H52O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26(27)28/h2-25H2,1H3,(H,27,28)

InChI Key

XMHIUKTWLZUKEX-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain 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 Framework

Aliphatic acyclic compounds

External Descriptors

very long-chain fatty acid (CHEBI:31009 )
straight-chain saturated fatty acid (CHEBI:31009 )
Straight chain fatty acids (LMFA01010026 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Adrenoleukodystrophy (HMDB: HMDB0002356)
Adrenomyeloneuropathy (HMDB: HMDB0002356)

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0002356)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0002356)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002356)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002356)

Organ

Gland

Adrenal Gland (HMDB: HMDB0002356)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002356)

Source

Endogenous

Endogenous (HMDB: HMDB0002356)

Plant

Plant (HMDB: HMDB0002356)
Fabaceae (HMDB: HMDB0002356)

Animal

Animal (HMDB: HMDB0002356)

Exogenous

Food

Food (HMDB: HMDB0002356)

Nut

Peanut (FooDB: FOOD00016)

Process

Role

Biological role

Energy source (HMDB: HMDB0002356)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002356)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	9.87	ALOGPS
logP	10.7	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	123.09 m³·mol⁻¹	ChemAxon
Polarizability	55.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon