(3S)-Hydroxy-tetracosa-6,9,12,15,18,21-all-cis-hexaenoyl-CoA (CHEM040913)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:04:32 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040913
Identification
Common Name(3S)-Hydroxy-tetracosa-6,9,12,15,18,21-all-cis-hexaenoyl-CoA
ClassSmall Molecule
Description(3S)-Hydroxy-tetracosa-6,9,12,15,18,21-all-cis-hexaenoyl-CoA is an acyl-CoA with (3S)-Hydroxy-tetracosa-6,9,12,15,18,21-all-cis-hexaenoate 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 compound undergoes beta oxidation, forming one or more molecules of acetyl-CoA. This, in turn, enters the citric acid cycle, eventually forming several molecules of ATP.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S)-3-Hydroxy-all-cis-6,9,12,15,18,21-tetracosahexaenoyl-CoAHMDB
(3S)-3-Hydroxy-all-cis-6,9,12,15,18,21-tetracosahexaenoyl-coenzyme AHMDB
(3S)-Hydroxynisinoyl-CoAHMDB
(3S)-Hydroxynisinoyl-coenzyme AHMDB
3SNisCoAHMDB
3SNiscoenzyme AHMDB
4-({[({[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-[(3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidateHMDB
4-({[({[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-[(3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl)sulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidateHMDB
4-({[({[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-[(3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl)sulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acidHMDB
Chemical FormulaC45H66N7O18P3S
Average Molecular Mass1118.028 g/mol
Monoisotopic Mass1117.340 g/mol
CAS Registry NumberNot Available
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
SMILESCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(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 IdentifierInChI=1S/C45H70N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-33(53)28-36(55)74-27-26-47-35(54)24-25-48-43(58)40(57)45(2,3)30-67-73(64,65)70-72(62,63)66-29-34-39(69-71(59,60)61)38(56)44(68-34)52-32-51-37-41(46)49-31-50-42(37)52/h5-6,8-9,11-12,14-15,17-18,20-21,31-34,38-40,44,53,56-57H,4,7,10,13,16,19,22-30H2,1-3H3,(H,47,54)(H,48,58)(H,62,63)(H,64,65)(H2,46,49,50)(H2,59,60,61)/p-4/b6-5-,9-8-,12-11-,15-14-,18-17-,21-20-/t33-,34-,38+,39+,40?,44-/m0/s1
InChI KeyJJCGUWRDULVWQG-VXLHGKKBSA-J
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
  • Alkyl phosphate
  • Imidolactam
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Pyrimidine
  • Phosphoric acid ester
  • Oxolane
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organoheterocyclic compound
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Oxacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Alcohol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Amine
  • Organonitrogen compound
  • 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 Solubility0.23 g/LALOGPS
logP3.6ALOGPS
logP0.75ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity281.67 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900111100-9f80a076ce441015a33bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900323000-99d480d3edea9bf27b59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900001000-e7e46016cd25a38149caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fur-3904140400-28235335399cbebf4a44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3901210100-5a7f5bc49a94ceb1ae82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-eaa17674839c6b4047ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-d45c1df0a1b3e1b28807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0629-4900101340-b29e510493dde37213a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9502300610-7a5faa144b696020d904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1900000000-591fcd8ed50c2dbc3065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9500000013-0a5545e09f90241ac4b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0000297000-7a5d8672628b953e4cccSpectrum
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 IDHMDB0012479
FooDB IDFDB029088
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID75955250
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. The lipid handbook with CD-ROM