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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:53:42 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0003947
Secondary Accession Numbers
  • HMDB03947
Metabolite Identification
Common Name8Z,11Z,14Z-eicosatrienoyl-CoA
Description

8Z,11Z,14Z-eicosatrienoyl-CoA participates in the biosynthesis of unsaturated fatty acids. 8Z,11Z,14Z-eicosatrienoyl-CoA is converted from (8Z,11Z,14Z)-Icosatrienoic acid via palmitoyl-CoA hydrolase [EC:3.1.2.2].

Unsaturated fatty acids are of similar form, except that one or more alkenyl functional groups exist along the chain, with each alkene substituting a single-bonded "-CH2-CH2-" part of the chain with a double-bonded "-CH=CH-" portion (that is, a carbon double-bonded to another carbon). The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes). (Wikipedia)

.
Structure
Data?1582752292
Synonyms
ValueSource
(8Z,11Z,14Z)-Eicosatrienoyl-coenzyme AChEBI
(8Z,11Z,14Z)-Icosatrienoyl-CoAChEBI
8,11,14-Eicosatrienoyl-CoAChEBI
8,11,14-Icosatrienoyl-CoAChEBI
8Z,11Z,14Z-Icosatrienoyl-CoAChEBI
all-cis-Eicosa-8,11,14-trienoyl-CoAChEBI
all-cis-Eicosa-8,11,14-trienoyl-coenzyme AChEBI
all-cis-Icosa-8,11,14-trienoyl-coenzyme AChEBI
CoA[20:3(8Z,11Z,14Z)]ChEBI
(8Z,11Z,14Z)-Icosa-8,11,14-trienoyl-CoAKegg
(8Z,11Z,14Z)-Eicosatrienoyl-CoAHMDB
(8Z,11Z,14Z)-Icosatrienoyl-coenzyme AHMDB
CoA(20:3(8Z,11Z,14Z))HMDB
Dihomo-gamma-linolenoyl-CoAHMDB
Dihomo-g-linolenoyl-CoAHMDB
Dihomo-γ-linolenoyl-CoAHMDB
(8Z,11Z,14Z)-eicosatrienoyl-CoA SMPDB, HMDB
(8Z,11Z,14Z)-eicosatrienoyl-coenzyme A SMPDB, ChEBI
(8Z,11Z,14Z)-icosatrienoyl-CoA SMPDB, ChEBI
(8Z,11Z,14Z)-icosatrienoyl-coenzyme A SMPDB, HMDB
8Z,11Z,14Z-Eicosatrienoyl-CoAChEBI
Chemical FormulaC41H68N7O17P3S
Average Molecular Weight1056.002
Monoisotopic Molecular Weight1055.360524011
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name8Z,11Z,14Z-eicosatrienoyl-coa
CAS Registry Number28879-98-3
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=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/C41H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h8-9,11-12,14-15,28-30,34-36,40,51-52H,4-7,10,13,16-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-/t30-,34-,35-,36+,40-/m1/s1
InChI KeyFJWJALRUNNZIBB-DDQUOPDJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 2-enoyl 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
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.045Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP3.36ALOGPS
logP1.29ChemAxon
logS-3.3ALOGPS
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
Refractivity258.4 m³·mol⁻¹ChemAxon
Polarizability106.36 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]+283.24930932474
DeepCCS[M-H]-281.52630932474
DeepCCS[M-2H]-315.90230932474
DeepCCS[M+Na]+290.09530932474
AllCCS[M+H]+302.932859911
AllCCS[M+H-H2O]+303.432859911
AllCCS[M+NH4]+302.332859911
AllCCS[M+Na]+302.232859911
AllCCS[M-H]-312.732859911
AllCCS[M+Na-2H]-319.032859911
AllCCS[M+HCOO]-325.732859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Negative-QTOFsplash10-0059-9605250500-791fd2d304e42cc798082017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Negative-QTOFsplash10-0059-5902220100-39a76969d0a2b88a66df2017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-81498ababc2aa3d49ca62017-09-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Positive-QTOFsplash10-000i-4905410200-85ab31da09b31425a7972017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Positive-QTOFsplash10-000i-1916320000-718c3ae6f913b160279d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Positive-QTOFsplash10-000i-1902200000-dbb93ca6456340bc53be2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Negative-QTOFsplash10-0udi-9000000000-c3efc1735c5fbb4d3d612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Negative-QTOFsplash10-0ug0-9010201300-645423b23dce79bfb95d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Negative-QTOFsplash10-004r-9002300302-3b58453e9b26892cb2d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Positive-QTOFsplash10-0a4i-9000000000-0e1b03ac420efbd887b82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Positive-QTOFsplash10-000i-7900100428-216a4affac4aa010da5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Positive-QTOFsplash10-0002-0100690000-a870a04548c6b749280a2021-09-24Wishart 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 IDFDB023266
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03595
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11966190
PDB IDNot Available
ChEBI ID27979
Food Biomarker OntologyNot Available
VMH IDDLNLCGCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
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 play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
General function:
Involved in thiolester hydrolase 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. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02