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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 10:00:05 UTC
Update Date2017-12-20 20:29:10 UTC
HMDB IDHMDB0006459
Secondary Accession Numbers
  • HMDB06459
Metabolite Identification
Common NameHexacosanoyl-CoA
DescriptionHexacosanoyl-coa , also known as 26:0 coa(4-) or c26:0-coenzyme a(4-), is a member of the class of compounds known as very long-chain fatty acyl coas. Very long-chain fatty acyl coas are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Hexacosanoyl-coa is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, hexacosanoyl-coa is primarily located in the cytoplasm, in the membrane (predicted from logP), in the mitochondria and in the peroxisome. It can also be found in the extracellular space. In humans, hexacosanoyl-coa is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Hexacosanoyl-coa is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. hexacosanoyl CoA is an intermediate in Biosynthesis of fatty acids. hexacosanoyl CoA (26:O CoA) oxidation was detected in peroxisomal and. mitochondrial fractions..
Structure
Thumb
Synonyms
ValueSource
26:0 CoA(4-)ChEBI
C26:0-CoA(4-)ChEBI
C26:0-coenzyme A(4-)ChEBI
Cerotoyl-CoA(4-)ChEBI
Cerotoyl-coenzyme A(4-)ChEBI
Hexacosanoyl-CoAChEBI
Hexacosanoyl-coenzyme A(4-)ChEBI
C26:0 CoAHMDB
C26:0 coenzyme AHMDB
Chemical FormulaC47H82N7O17P3S
Average Molecular Weight1142.177
Monoisotopic Molecular Weight1141.470074459
IUPAC Name(3R)-3-[(2-{[2-(hexacosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
Traditional Name(3R)-3-[(2-{[2-(hexacosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C47H86N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-38(56)75-31-30-49-37(55)28-29-50-45(59)42(58)47(2,3)33-68-74(65,66)71-73(63,64)67-32-36-41(70-72(60,61)62)40(57)46(69-36)54-35-53-39-43(48)51-34-52-44(39)54/h34-36,40-42,46,57-58H,4-33H2,1-3H3,(H,49,55)(H,50,59)(H,63,64)(H,65,66)(H2,48,51,52)(H2,60,61,62)/p-4/t36-,40-,41-,42+,46-/m1/s1
InChI KeyFHLYYFPJDVYWQH-CPIGOPAHSA-J
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentVery long-chain fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • N-substituted imidazole
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Monosaccharide
  • Pyrimidine
  • Fatty amide
  • Phosphoric acid ester
  • Imidolactam
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Primary amine
  • Organic oxide
  • Amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP5.32ALOGPS
logP3.95ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area374.95 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity278.17 m³·mol⁻¹ChemAxon
Polarizability121.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Adrenoleukodystrophy, X-linkedThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Beta Oxidation of Very Long Chain Fatty AcidsThumbThumb?image type=greyscaleThumb?image type=simpleMap01040
Carnitine-acylcarnitine translocase deficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023919
KNApSAcK IDNot Available
Chemspider ID28184701
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID1453342
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25202335
PDB IDNot Available
ChEBI ID64868
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name:
ACSL1
Uniprot ID:
P33121
Molecular weight:
77942.685