Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:10:04 UTC
Update Date2022-03-07 02:51:27 UTC
HMDB IDHMDB0012930
Secondary Accession Numbers
  • HMDB12930
Metabolite Identification
Common NameDocosanoyl-CoA
DescriptionDocosanoyl-CoA is an acyl-CoA with the C-22 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine.
Structure
Data?1582753078
Synonyms
ValueSource
Behenoyl-CoAHMDB
Behenoyl-coenzyme AHMDB
Chemical FormulaC43H78N7O17P3S
Average Molecular Weight1090.11
Monoisotopic Molecular Weight1089.438776248
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)
InChI KeyNDDZLVOCGALPLR-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Pyrimidine
  • Phosphoric acid ester
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Organic 1,3-dipolar compound
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Primary amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.88ALOGPS
logP3.27ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity264.25 m³·mol⁻¹ChemAxon
Polarizability114.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+259.84930932474
DeepCCS[M-H]-258.03930932474
DeepCCS[M-2H]-292.07430932474
DeepCCS[M+Na]+265.8530932474
AllCCS[M+H]+311.632859911
AllCCS[M+H-H2O]+312.132859911
AllCCS[M+NH4]+311.132859911
AllCCS[M+Na]+310.932859911
AllCCS[M-H]-296.632859911
AllCCS[M+Na-2H]-302.132859911
AllCCS[M+HCOO]-308.132859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 10V, Positive-QTOFsplash10-000i-4901220100-ad430b543fc1cc3c9d1c2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 20V, Positive-QTOFsplash10-000i-1901340000-36d071c4e3f230a578232019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-ebb26a1d3ef41618acad2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 10V, Negative-QTOFsplash10-00v0-9615240500-17e4235039f190ce32d32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 20V, Negative-QTOFsplash10-001i-5902220100-09ac1e3e39670fff85a32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-dd56c2d9e9d82a3d3e212019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 10V, Positive-QTOFsplash10-0006-9000000000-937c9f6c24c43db1e4312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 20V, Positive-QTOFsplash10-000i-9800100415-8f6041d6075a75e901d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 40V, Positive-QTOFsplash10-001i-0000390000-b579264e92d1412582102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 10V, Negative-QTOFsplash10-000i-9000000000-97b2abe320fd4ab2ff9b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 20V, Negative-QTOFsplash10-000i-9001201300-c011a19f1678d65394272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanoyl-CoA 40V, Negative-QTOFsplash10-004j-9101200200-3f7fec23cf270a784a232021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB029210
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74346883
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDDOCOSCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
ACOT8
Uniprot ID:
O14734
Molecular weight:
35914.02
General function:
Involved in copper ion binding
Specific function:
Mediates the post-translational oxidative deamination of lysine residues on target proteins leading to the formation of deaminated lysine (allysine). When secreted in extracellular matrix, promotes cross-linking of extracellular matrix proteins by mediating oxidative deamination of peptidyl lysine residues in precursors to fibrous collagen and elastin. Acts as a regulator of sprouting angiogenesis, probably via collagen IV scaffolding. When nuclear, acts as a transcription corepressor and specifically mediates deamination of trimethylated 'Lys-4' of histone H3 (H3K4me3), a specific tag for epigenetic transcriptional activation. Involved in epithelial to mesenchymal transition (EMT) via interaction with SNAI1 and participates in repression of E-cadherin, probably by mediating deamination of histone H3. Also involved in E-cadherin repression following hypoxia, a hallmark of epithelial to mesenchymal transition believed to amplify tumor aggressiveness, suggesting that it may play a role in tumor progression. Acts as a regulator of chondrocyte differentiation, probably by regulating expression of factors that control chondrocyte differentiation.
Gene Name:
LOXL2
Uniprot ID:
Q9Y4K0
Molecular weight:
86724.305
General function:
Involved in cell cycle
Specific function:
Interacts with the components of the replication complex and 2 kinases, CDK2 and CDC7, thereby providing a functional and physical link between CDK2 and CDC7 during firing of the origins of replication. Regulates ATR-mediated checkpoint signaling
Gene Name:
CINP
Uniprot ID:
Q9BW66
Molecular weight:
24323.6
General function:
Translation, ribosomal structure and biogenesis
Specific function:
May play a role in chromatin function and histone metabolism via its interaction with HIRA and histones
Gene Name:
HIRIP3
Uniprot ID:
Q9BW71
Molecular weight:
61956.5
General function:
Involved in carboxylesterase activity
Specific function:
Not Available
Gene Name:
ACOT6
Uniprot ID:
Q3I5F7
Molecular weight:
22990.5