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2,3-dehydroadipyl-CoA (M2MDB003553)

Record Information
Version2.0
Creation Date2012-10-10 12:19:55 -0600
Update Date2015-06-03 17:26:04 -0600
Secondary Accession Numbers
  • ECMDB23163
Identification
Name:2,3-dehydroadipyl-CoA
Description2,3-Dehydroadipyl-CoA is an intermediate in phenylacetate degradation. It is a substrate for the enzyme 2,3-dehydroadipyl-CoA hydratase which catalyzes the reversible conversion of enzymatically produced 2,3-dehydroadipyl-CoA into 3-hydroxyadipyl-CoA.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (9R,20E)-1-(2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl-3,5,9-trihydroxy-8,8-dimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatetracos -20-en-24-Oate 3,5-dioxide (non-preferred name)
  • (9R,20E)-1-(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl-3,5,9-trihydroxy-8,8-dimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatetracos -20-en-24-oic acid 3,5-dioxide (non-preferred name)
  • (E)-3,4-dehydroadipoyl-CoA
  • (e)-6-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-6-oxohex-4-enoate
  • (E)-6-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-6-oxohex-4-enoic acid
  • (e)-6-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-6-oxohex-4-enoate
  • (e)-6-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-6-oxohex-4-enoic acid
  • 2,3-Dehydroadipyl-CoA
  • 2,3-Didehydroadipyl-CoA
  • 5-Carboxy-2-pentenoyl-CoA
Chemical Formula:C27H42N7O19P3S
Weight:Average: 893.644
Monoisotopic: 893.146902423
InChI Key:ZFXICKRXPZTFPB-KCQRSJHASA-N
InChI:InChI=1S/C27H42N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h4,6,13-15,20-22,26,39-40H,3,5,7-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b6-4+/t15-,20-,21-,22+,26-/m1/s1
CAS number:Not Available
IUPAC Name:(4E)-6-[(2-{3-[(2R)-3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-6-oxohex-4-enoic acid
Traditional IUPAC Name:trans-2,3-didehydroadipoyl-coa
SMILES:O[C@H](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)C(=O)NCCC(=O)NCCSC(=O)\C=C\CCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Hydroxybenzoic acid
  • Monocyclic monoterpenoid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-5
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.16 g/LALOGPS
logP-0.21ALOGPS
logP-6ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.4 m³·mol⁻¹ChemAxon
Polarizability77.98 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2,3-dehydroadipyl-CoA + Acetyl-CoA > CoA + 3-Oxo-5,6-dehydrosuberyl-CoA
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1922000130-7f64797205f4c5a0799dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0933000000-02ff8b4f16369cd99c6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-dccaccec5a4ef0c29d6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-3911030450-c20f26f9727f01bfff34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3911010010-c72024d64ac9c2d76bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-c0c56fb21cc884106020View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004u-0200000090-be9fb26b71e54a88c466View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000160-224040439203b998045fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0119000000-17a09959c8b36d05b052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-5ff647d6f62bf4c645f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0597-5800001690-98c1caedf251d7207161View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9202423730-7094fc194ad3dbe28e06View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID68471
HMDB IDHMDB0060392
Pubchem Compound ID24798711
Kegg IDC14144
ChemSpider ID21865675
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Beta-ketoadipyl-CoA thiolase
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes thiolytic cleavage of beta-ketoadipyl-CoA to succinyl-CoA and acetyl-CoA
Gene Name:
paaJ
Uniprot ID:
P0C7L2
Molecular weight:
42276
Reactions
Succinyl-CoA + acetyl-CoA = CoA + 3-oxoadipyl-CoA.
2,3-dehydroadipyl-CoA + acetyl-CoA = CoA + 3-oxo-5,6-dehydrosuberyl-CoA.