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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:52:28 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060312
Secondary Accession Numbers
  • HMDB60312
Metabolite Identification
Common Name(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA
Description(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA, also known as (6Z,9Z,12Z,15Z,18Z,21Z)-3-hydroxytetracosahexaenoyl-coenzyme A or 1-3-hydroxy-tha-CoA, 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. Thus, (6Z,9Z,12Z,15Z,18Z,21Z)-3-hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA is considered to be a fatty ester lipid molecule (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866042
Synonyms
ValueSource
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosa-6,9,12,15,18,21-hexaenoyl-CoAChEBI
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosa-6,9,12,15,18,21-hexaenoyl-coenzyme AChEBI
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexaenoyl-coenzyme AChEBI
1-(3-Hydroxy-6Z,9Z,12Z,15Z,18Z,21Z-tetracosahexaenoyl)-CoAChEBI
1-3-Hydroxy-tha-CoAChEBI
CoA(24:6(6Z,9Z,12Z,15Z,18Z,21Z)(3oh))ChEBI
Chemical FormulaC45H70N7O18P3S
Average Molecular Weight1122.06
Monoisotopic Molecular Weight1121.371088697
IUPAC Name(2R)-4-({[({[(2R,3S,4R,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-{[(6Z,9Z,12Z,15Z,18Z,21Z)-3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
Traditional Name(2R)-4-[({[(2R,3S,4R,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-{[(6Z,9Z,12Z,15Z,18Z,21Z)-3-hydroxytetracosa-6,9,12,15,18,21-hexaenoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)CC(=O)SCCN=C(O)CCN=C(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=C(N)N=CN=C12
InChI Identifier
InChI=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)/b6-5-,9-8-,12-11-,15-14-,18-17-,21-20-/t33?,34-,38-,39-,40+,44-/m1/s1
InChI KeyJJCGUWRDULVWQG-MOYVEXGTSA-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

Source

Route of exposure

Physical Properties
StateNot Available
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 Solubility0.053 g/LALOGPS
logP3.82ALOGPS
logP2.35ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area390.84 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity282.71 m³·mol⁻¹ChemAxon
Polarizability110.71 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]-321.89330932474
DeepCCS[M+Na]+296.11730932474
AllCCS[M+H]+318.532859911
AllCCS[M+H-H2O]+318.932859911
AllCCS[M+NH4]+318.032859911
AllCCS[M+Na]+317.932859911
AllCCS[M-H]-334.932859911
AllCCS[M+Na-2H]-341.032859911
AllCCS[M+HCOO]-347.532859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA 10V, Positive-QTOFsplash10-0f79-1900430100-99d4ce646779c2e5437c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA 20V, Positive-QTOFsplash10-0019-1901631000-8b41ebc707a562c63fa42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA 40V, Positive-QTOFsplash10-000i-1900210000-cb0be845429f35a917502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA 10V, Negative-QTOFsplash10-0fai-2904131400-6806bd7af223037338cc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA 20V, Negative-QTOFsplash10-001i-3901110100-87a5455ea7b10fc075522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-7d28293dff82640ec72a2017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDC16375
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70678621
PDB IDNot Available
ChEBI ID65130
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA → Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA + Waterdetails
(6Z,9Z,12Z,15Z,18Z,21Z)-3-Hydroxytetracosahexa-6,9,12,15,18,21-enoyl-CoA + NAD → (6Z,9Z,12Z,15Z,18Z,21Z)-3-Oxotetracosahexa-6,9,12,15,18,21-enoyl-CoA + NADH + Hydrogen Iondetails