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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002289
Secondary Accession Numbers
  • HMDB02289
Metabolite Identification
Common Name2-trans,4-trans-Octadienoyl-CoA
Description2-trans,4-trans-Octadienoyl-CoA belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms. Based on a literature review a significant number of articles have been published on 2-trans,4-trans-Octadienoyl-CoA.
Structure
Data?1582752241
Synonyms
ValueSource
S-[2E,4E]-OctadienoateHMDB
S-[2E,4E]-Octadienoate CoAHMDB
S-[2E,4E]-Octadienoate coenzyme AHMDB
S-[2E,4E]-Octadienoic acidHMDB
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-3,3-dimethyl-N-[2-({2-[(2E,4E)-octa-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidateGenerator, HMDB
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-3,3-dimethyl-N-[2-({2-[(2E,4E)-octa-2,4-dienoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidateGenerator, HMDB
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-3,3-dimethyl-N-[2-({2-[(2E,4E)-octa-2,4-dienoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acidGenerator, HMDB
Chemical FormulaC29H46N7O17P3S
Average Molecular Weight889.699
Monoisotopic Molecular Weight889.188373307
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E,4E)-octa-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E,4E)-octa-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number74418-29-4
SMILES
CCC\C=C\C=C\C(=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 Identifier
InChI=1S/C29H46N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h6-9,16-18,22-24,28,39-40H,4-5,10-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/b7-6+,9-8+/t18-,22-,23-,24?,28-/m1/s1
InChI KeyHOQIPZYVEOMJGX-LEIHBCTOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentMedium-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
  • 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
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility2.45 g/LALOGPS
logP0.61ALOGPS
logP-4.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity202.05 m³·mol⁻¹ChemAxon
Polarizability82.56 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]+241.38830932474
DeepCCS[M-H]-239.46530932474
DeepCCS[M-2H]-273.49630932474
DeepCCS[M+Na]+247.56930932474
AllCCS[M+H]+268.632859911
AllCCS[M+H-H2O]+269.132859911
AllCCS[M+NH4]+268.232859911
AllCCS[M+Na]+268.032859911
AllCCS[M-H]-265.032859911
AllCCS[M+Na-2H]-269.932859911
AllCCS[M+HCOO]-275.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-trans,4-trans-Octadienoyl-CoACCC\C=C\C=C\C(=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=C2N6787.2Standard polar33892256
2-trans,4-trans-Octadienoyl-CoACCC\C=C\C=C\C(=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=C2N4747.0Standard non polar33892256
2-trans,4-trans-Octadienoyl-CoACCC\C=C\C=C\C(=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=C2N6904.7Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 10V, Positive-QTOFsplash10-000i-2911000220-dcc1a2b1692dd69f85f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 20V, Positive-QTOFsplash10-000i-0933000000-12ff3f5fea875e8271b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 40V, Positive-QTOFsplash10-000i-1911000000-3a4acd3b28140a5b026b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 10V, Negative-QTOFsplash10-00v0-2911030330-66c9d4ef022d7a014b6f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 20V, Negative-QTOFsplash10-001i-4901010000-83ea772b5d273ef63ef12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 40V, Negative-QTOFsplash10-057i-5900000000-4a9a5e661940bdb6988f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 10V, Positive-QTOFsplash10-0006-0000000190-9a9ffa7a0d893f75a3522021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 20V, Positive-QTOFsplash10-000i-2700000390-3a9bc259d349a6e596fc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 40V, Positive-QTOFsplash10-001i-0119000000-4e328b3244ef81fe07932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 10V, Negative-QTOFsplash10-000i-0000000090-20bbfc6499e5d2c2b9c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 20V, Negative-QTOFsplash10-000i-5500203690-ea31449f7e210acd751e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-trans,4-trans-Octadienoyl-CoA 40V, Negative-QTOFsplash10-00n0-6104703920-f05d965e52fcd22662502021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB022951
KNApSAcK IDNot Available
Chemspider ID13628330
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6596
PubChem Compound21252282
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. Smeland TE, Nada M, Cuebas D, Schulz H: NADPH-dependent beta-oxidation of unsaturated fatty acids with double bonds extending from odd-numbered carbon atoms. Proc Natl Acad Sci U S A. 1992 Aug 1;89(15):6673-7. [PubMed:1495956 ]
  2. Mizugaki M, Kimura C, Kondo A, Kawaguchi A, Okuda S, Yamanaka H: Studies on the metabolism of unsaturated fatty acids. XIII. Properties of 2,4-dienoyl-CoA reductase from beef liver. J Biochem. 1984 Feb;95(2):311-7. [PubMed:6370988 ]
  3. Mizugaki M, Koeda N, Kondo A, Kimura C, Yamanaka H: Studies on the metabolism of unsaturated fatty acids. XVI. Purification and general properties of 2,4-dienoyl-CoA reductase from Candida lipolytica. J Biochem. 1985 Mar;97(3):837-43. [PubMed:4019437 ]