Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 20:09:16 UTC
Update Date2022-03-07 02:49:30 UTC
HMDB IDHMDB0006260
Secondary Accession Numbers
  • HMDB06260
Metabolite Identification
Common NameTrans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA
DescriptionTrans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-coa, also known as TChpCoA or TCHPcoenzyme A, is classified as a member of the very long-chain 2-enoyl coas. Very long-chain 2-enoyl CoAs are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of at least 22 carbon atoms. Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-coa is considered to be a practically insoluble (in water) and an extremely strong acidic compound. Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-coa can be found anywhere throughout a human cell.
Structure
Data?1582752377
Synonyms
ValueSource
2E,6Z,9Z,12Z,15Z,18Z,21Z-Tetracosaheptaenoyl-CoAHMDB
2E,6Z,9Z,12Z,15Z,18Z,21Z-Tetracosaheptaenoyl-coenzyme AHMDB
TChpCoAHMDB
TCHPcoenzyme 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-3,3-dimethyl-N-(2-{[2-(tetracosa-2,6,9,12,15,18,21-heptaenoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidateHMDB
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosa-2,6,9,12,15,18,21-heptaenoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidateHMDB
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosa-2,6,9,12,15,18,21-heptaenoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acidHMDB
Chemical FormulaC45H68N7O17P3S
Average Molecular Weight1104.05
Monoisotopic Molecular Weight1103.360525926
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetracosa-2,6,9,12,15,18,21-heptaenoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})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-2,2-dimethyl-3-[(2-{[2-(tetracosa-2,6,9,12,15,18,21-heptaenoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCC=CCC=CCC=CCC=CCC=CCC=CCCC=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C45H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-36(54)73-29-28-47-35(53)26-27-48-43(57)40(56)45(2,3)31-66-72(63,64)69-71(61,62)65-30-34-39(68-70(58,59)60)38(55)44(67-34)52-33-51-37-41(46)49-32-50-42(37)52/h5-6,8-9,11-12,14-15,17-18,20-21,24-25,32-34,38-40,44,55-56H,4,7,10,13,16,19,22-23,26-31H2,1-3H3,(H,47,53)(H,48,57)(H,61,62)(H,63,64)(H2,46,49,50)(H2,58,59,60)
InChI KeyNVOWZIBKQIWTDG-UHFFFAOYSA-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
  • 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility0.052 g/LALOGPS
logP4.2ALOGPS
logP2.21ChemAxon
logS-4ALOGPS
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
Refractivity281.25 m³·mol⁻¹ChemAxon
Polarizability109.94 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]+265.53130932474
DeepCCS[M-H]-262.23330932474
DeepCCS[M-2H]-297.93530932474
DeepCCS[M+Na]+273.32930932474
AllCCS[M+H]+317.632859911
AllCCS[M+H-H2O]+318.032859911
AllCCS[M+NH4]+317.132859911
AllCCS[M+Na]+317.032859911
AllCCS[M-H]-333.532859911
AllCCS[M+Na-2H]-339.632859911
AllCCS[M+HCOO]-346.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 10V, Positive-QTOFsplash10-000i-4901120100-7f8858f862870265518b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 20V, Positive-QTOFsplash10-000i-1901340000-853b4dd6837fd0c60a2e2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-3c97d732115cd82502712019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 10V, Negative-QTOFsplash10-001r-5904240500-22bb029d3d85853ee2e22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 20V, Negative-QTOFsplash10-001i-5903220100-772bb7cd4e88d2bcf6482019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-546ffadf4723438fea062019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 10V, Negative-QTOFsplash10-0udi-0900000000-0439aa63591f912522a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 20V, Negative-QTOFsplash10-0ufr-5902302410-4954f58fe11b2b17b12f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 40V, Negative-QTOFsplash10-004i-9001200300-c9c4e2386b2ac1008f1c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 10V, Positive-QTOFsplash10-0udi-1900000010-257e43a8140b479f98aa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 20V, Positive-QTOFsplash10-0019-8600100109-2f7a0daf8a9b90f016a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA 40V, Positive-QTOFsplash10-0002-0000390000-b6aaa0f38851c8ad4d712021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
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 IDFDB023865
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16374
BioCyc IDNot Available
BiGG ID2219652
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75955249
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE4828
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:
ACOX1
Uniprot ID:
Q15067
Molecular weight:
70135.205
Reactions
Tetracosahexaenoyl CoA + FAD → Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA + FADHdetails
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Oxidizes the CoA-esters of 2-methyl-branched fatty acids (By similarity).
Gene Name:
ACOX3
Uniprot ID:
O15254
Molecular weight:
69574.075
Reactions
Tetracosahexaenoyl CoA + FAD → Trans-2-all-cis-6,9,12,15,18,21-tetracosaheptaenoyl-CoA + FADHdetails
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