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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:33:36 UTC
Update Date2022-03-07 03:17:50 UTC
HMDB IDHMDB0062215
Secondary Accession Numbers
  • HMDB62215
Metabolite Identification
Common Name11Z,14Z-eicosadienoyl-CoA
DescriptionCoa(20:2(11z,14z)) belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Thus, CoA(20:2(11Z,14Z)) is considered to be a fatty ester lipid molecule. Coa(20:2(11z,14z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866280
SynonymsNot Available
Chemical FormulaC41H70N7O17P3S
Average Molecular Weight1058.02
Monoisotopic Molecular Weight1057.37617599
IUPAC Name(2R)-4-({[({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(11Z,14Z)-icosa-11,14-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
Traditional Name(2R)-4-[({[(2R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-[2-({2-[(11Z,14Z)-icosa-11,14-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCCCC(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)C([H])(O)C1([H])OP(O)(O)=O
InChI Identifier
InChI=1S/C41H70N7O17P3S/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/h8-9,11-12,28-30,34-36,40,51-52H,4-7,10,13-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-/t30-,34?,35?,36+,40-/m1/s1
InChI KeyYCKYOUVXZZJCIU-DKSPDXACSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Pentacarboxylic acid or derivatives
  • Alpha-amino acid ester
  • Alkyl-phenylketone
  • Macrolide
  • Macrolactam
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Phenylketone
  • Indole
  • Indole or derivatives
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous amide
  • Cyclic carboximidic acid
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Ketone
  • Lactone
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 g/lALOGPS
LogP3.35ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.64ALOGPS
logP1.92ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity258.33 m³·mol⁻¹ChemAxon
Polarizability106.55 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-2H]-313.40230932474
DeepCCS[M+Na]+287.67630932474
AllCCS[M+H]+302.832859911
AllCCS[M+H-H2O]+303.432859911
AllCCS[M+NH4]+302.332859911
AllCCS[M+Na]+302.132859911
AllCCS[M-H]-311.932859911
AllCCS[M+Na-2H]-318.132859911
AllCCS[M+HCOO]-324.932859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 10V, Positive-QTOFsplash10-000i-4905410200-daedb35bb66be31afc5d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 20V, Positive-QTOFsplash10-000i-1916320000-81bda577e044a04c113f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 40V, Positive-QTOFsplash10-000i-1902200000-933b34a0c77ced235c962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 10V, Negative-QTOFsplash10-0569-9741331500-04300626f896e0e69ad72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 20V, Negative-QTOFsplash10-001i-4910210100-5232a50261651c12d3b52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 40V, Negative-QTOFsplash10-057i-5900000000-d42c2f4170cbba664de12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 10V, Positive-QTOFsplash10-0a4i-9000000000-6b007895e40106c9de542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 20V, Positive-QTOFsplash10-0pwc-9000100317-24a8afa7808d43526eee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 40V, Positive-QTOFsplash10-0udi-0100590000-4c0a1143fb9e4b62db2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 10V, Negative-QTOFsplash10-0a4i-9000000000-0109ddbabbc3530544b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 20V, Negative-QTOFsplash10-0zi9-9000102100-153e04727842fd45e3982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11Z,14Z-eicosadienoyl-CoA 40V, Negative-QTOFsplash10-004r-9000200101-8a443940f5f782d06dcf2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922024
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.