Eicosanoyl-CoA (CHEM035667)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:58:23 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035667
Identification
Common NameEicosanoyl-CoA
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Arachidinoyl-CoAHMDB
Arachidinoyl-coenzyme AHMDB
Arachidoyl coenzyme AHMDB
Arachidoyl-CoAHMDB
Arachidoyl-coenzyme AHMDB
Arachidyl CoAHMDB
Arachidyl coenzyme AHMDB
EicosanethioateHMDB
Eicosanethioic acidHMDB
Eicosanethioic acid S-ester with coenzyme AHMDB
Eicosanoyl coenzyme AHMDB
Eicosyl-coenzyme AHMDB
Icosanoyl-CoAHMDB
S-EicosanoateHMDB
S-Eicosanoate CoAHMDB
S-Eicosanoate coenzyme AHMDB
S-Eicosanoic acidHMDB
Chemical FormulaC41H74N7O17P3S
Average Molecular Mass1062.049 g/mol
Monoisotopic Mass1061.407 g/mol
CAS Registry Number15895-27-9
IUPAC Name(2R)-4-({[({[(2R,3R,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-(icosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid
Traditional Name(2R)-4-[({[(2R,3R,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-(icosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid
SMILESCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI IdentifierInChI=1S/C41H74N7O17P3S/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/h28-30,34-36,40,51-52H,4-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t30-,34?,35+,36+,40-/m1/s1
InChI KeyJYLSVNBJLYCSSW-OPBWFHODSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.49 g/LALOGPS
logP3.37ALOGPS
logP2.64ChemAxon
logS-3.3ALOGPS
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 Count38ChemAxon
Refractivity256.1 m³·mol⁻¹ChemAxon
Polarizability110.55 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-01p9-0006009000-6e1a793d809085ba3686Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-05n1-0009600000-e13e270a6f88f6a5a3ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-03di-0029002100-08cbd6ea757ed07a6da0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-0a4i-0259300000-61c2eb22cd5e2a3f2cf2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-03e9-0002108900-47877dcbff98f191ea53Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-001j-0001009000-89d4b9c78187c317d546Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 110V, negativesplash10-0a4i-4010900100-0aa4b3051c977f77985aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 131V, negativesplash10-0ab9-4553901100-818b511dd6840453cb35Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 165V, negativesplash10-05di-8944200000-5fd4b285d9afcabf241bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 197V, negativesplash10-056r-9612000000-87cd59c13fc96eb6eb95Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 242V, negativesplash10-004i-9510000000-b517c25068f9c1982e8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 286V, negativesplash10-004i-9400000000-a4234a53ca0e7646c30cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-0bt9-0000304809-6c90b79308cfb7a85633Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-00di-0290000000-b25cca751af0dd2badcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-000i-0009000000-6ef6afc6fe6085ff5e73Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-0a4l-0591000000-a05636d3cefb5ba9bd1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-014i-0019100000-038393513fe0be3e4ae6Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-001i-0001009700-ace2df889878b9cbcf3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 74V, negativesplash10-001i-0000009100-01c2f8eafda393f29223Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-4906510200-33a73d163e145dfbbae4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1916320000-56005ad0a13bdbef157cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2903100000-7f72125411656ae21e0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01sl-9631331400-1cb65302d061f1beb679Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910210100-f84d357466fe668f4379Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8900100000-836e8e4b990877787e04Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004258
FooDB IDFDB023354
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDICOSANOYL-COA
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17220830
ChEBI ID15527
PubChem Compound ID16061151
Kegg Compound IDC02041
YMDB IDYMDB16181
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lellouche, Jean-Paul; Levannier, Karine; Mioskowski, Charles. Process for synthesizing fatty acid-acylated thiol transporter derivatives, particularly of acyl coenzyme A derivatives, and the acyl coenzyme A derivatives thus obtained. Eur. Pat. Appl. (1994), 18 pp. CODEN: EPXXDW EP 618218 A1 19941005 CAN 123:170077 AN 1995:761488
2. Agarwal AK, Sukumaran S, Bartz R, Barnes RI, Garg A: Functional characterization of human 1-acylglycerol-3-phosphate-O-acyltransferase isoform 9: cloning, tissue distribution, gene structure, and enzymatic activity. J Endocrinol. 2007 Jun;193(3):445-57.
3. O'Byrne J, Hunt MC, Rai DK, Saeki M, Alexson SE: The human bile acid-CoA:amino acid N-acyltransferase functions in the conjugation of fatty acids to glycine. J Biol Chem. 2003 Sep 5;278(36):34237-44. Epub 2003 Jun 16.