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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 13:18:05 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006513
Secondary Accession Numbers
  • HMDB06513
Metabolite Identification
Common NameDocosa-4,7,10,13,16-pentaenoyl CoA
Description(4Z,7Z,10Z,13Z,16Z)-Docosapentaenoyl-CoA is an intermediate in the biosynthesis of unsaturated fatty acids. (4Z,7Z,10Z,13Z,16Z)-Docosapentaenoyl-CoA is produced from (7Z,10Z,13Z,16Z)-Docosatetraenoyl-CoA via thiol ester hydrolases (EC 3.1.2.-) or from (6Z,9Z,12Z,15Z,18Z)-Tetracosapentaenoyl-CoA via the enzyme fatty acyl-CoA oxidase (EC 1.3.3.6 ). 4Z,7Z,10Z,13Z,16Z)-Docosapentaenoyl-CoA can also be used in the synthesis of (6Z,9Z,12Z,15Z,18Z)-3-Oxotetracosapenta-6,9,12,15,18-enoyl-CoA via the enzyme acetyl-CoA acyltransferase 1 (EC:2.3.1.16).
Structure
Data?1582752388
Synonyms
ValueSource
(4Z,7Z,10Z,13Z,16Z)-Docosapentaenoyl-coenzyme AChEBI
Docosa-4,7,10,13,16-pentaenoyl coenzyme AChEBI
(4Z,7Z,10Z,13Z,16Z)-Docosapentaenoyl-CoAHMDB
4,7,10,13,16-Docosapentaenoyl coenzyme AHMDB
Docosa-4,7,10,13,16-pentaenoyl-CoAHMDB
Docosa-4,7,10,13,16-pentaenoyl-coenzyme AHMDB
Osbondoyl-coenzyme AHMDB
CoA(22:5(4Z,7Z,10Z,13Z,16Z))HMDB
Osbondoyl-CoAHMDB
Chemical FormulaC43H68N7O17P3S
Average Molecular Weight1080.03
Monoisotopic Molecular Weight1079.360525926
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoylsulfanyl]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[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number30960-17-9
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=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/C43H68N7O17P3S/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/h8-9,11-12,14-15,17-18,20-21,30-32,36-38,42,53-54H,4-7,10,13,16,19,22-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/b9-8-,12-11-,15-14-,18-17-,21-20-/t32-,36-,37-,38+,42-/m1/s1
InChI KeyQKBTYZDPVNTERQ-UWVCYPHHSA-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
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility0.25 g/LALOGPS
logP3.84ALOGPS
logP1.46ChemAxon
logS-3.6ALOGPS
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 Count35ChemAxon
Refractivity269.84 m³·mol⁻¹ChemAxon
Polarizability105.43 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]+277.9230932474
DeepCCS[M-H]-276.14530932474
DeepCCS[M-2H]-311.77630932474
DeepCCS[M+Na]+286.20830932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 10V, Negative-QTOFsplash10-07gi-9715250500-b1dcbab6c75c404f854e2017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 20V, Negative-QTOFsplash10-001i-4902120100-eabbc8408d723ab9535f2017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 40V, Negative-QTOFsplash10-057i-5900100000-b92e67d4926b9c931aa82017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 10V, Positive-QTOFsplash10-000i-4902120200-73950ead7bd33dace3242017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 20V, Positive-QTOFsplash10-000i-1903140000-2c527b6bdb2b2c79c74a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 40V, Positive-QTOFsplash10-000i-1900010000-b2b90175b03a0c545b1d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 10V, Negative-QTOFsplash10-004i-9000000000-925b6402de9fe7f74a102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 20V, Negative-QTOFsplash10-004i-9001201300-351ce645cfa9ddf851072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 40V, Negative-QTOFsplash10-004r-9001300300-5347ffb0028e566b51ca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 10V, Positive-QTOFsplash10-001i-9000000000-b3ff8ff905d8308eb25a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 20V, Positive-QTOFsplash10-000i-7700100209-1e19b4653f209a3be9ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosa-4,7,10,13,16-pentaenoyl CoA 40V, Positive-QTOFsplash10-00di-0000490000-d08f141676ac4df5e3ff2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
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 IDFDB023952
KNApSAcK IDNot Available
Chemspider ID30785928
KEGG Compound IDC16173
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71448905
PDB IDNot Available
ChEBI ID76450
Food Biomarker OntologyNot Available
VMH IDDCSPTN1COA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
Reactions
Docosa-4,7,10,13,16-pentaenoyl CoA + Acetyl-CoA → Coenzyme A + (6Z,9Z,12Z,15Z,18Z)-3-Oxotetracosapenta-6,9,12,15,18-enoyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955