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2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA (M2MDB003549)

Record Information
Version2.0
Creation Date2012-10-10 12:19:38 -0600
Update Date2015-06-03 17:26:03 -0600
Secondary Accession Numbers
  • ECMDB23159
Identification
Name:2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
Description2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA is an intermediate in phenylacetate metabolism. It is a substrate for 1,2-phenylacetyl-CoA epoxidase which catalyzes the reduction of phenylacetyl-CoA (PA-CoA) to form 1,2-epoxyphenylacetyl-CoA. The subunit A is the catalytic subunit involved in the incorporation of one atom of molecular oxygen into phenylacetyl-CoA
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • S-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-dimethylbutanoylaminopropanoylaminoethyl 2-(7-oxabicyclo4.1.0hepta-2,4-dien-6-yl)ethanethioate
  • S-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-dimethylbutanoylaminopropanoylaminoethyl 2-(7-oxabicyclo4.1.0Hepta-2,4-dien-6-yl)ethanethioic acid
Chemical Formula:C29H42N7O18P3S
Weight:Average: 901.666
Monoisotopic: 901.151987801
InChI Key:ZTMHVINYLDVBNO-FOGVYBFTSA-N
InChI:InChI=1S/C29H42N7O18P3S/c1-28(2,23(40)26(41)32-8-6-18(37)31-9-10-58-19(38)11-29-7-4-3-5-17(29)52-29)13-50-57(47,48)54-56(45,46)49-12-16-22(53-55(42,43)44)21(39)27(51-16)36-15-35-20-24(30)33-14-34-25(20)36/h3-5,7,14-17,21-23,27,39-40H,6,8-13H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t16-,17?,21-,22-,23+,27-,29?/m1/s1
CAS number:Not Available
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-3,3-dimethyl-N-[2-({2-[(2-{7-oxabicyclo[4.1.0]hepta-2,4-dien-1-yl}acetyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid
Traditional IUPAC 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-3,3-dimethyl-N-[2-({2-[(2-{7-oxabicyclo[4.1.0]hepta-2,4-dien-1-yl}acetyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid
SMILES:[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC12OC1([H])C=CC=C2)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Imidolactam
  • Alkyl phosphate
  • Phosphoric acid ester
  • N-acyl-amine
  • N-substituted imidazole
  • Pyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Sulfenyl compound
  • Dialkyl ether
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Ether
  • Oxirane
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.48 g/LALOGPS
logP0.24ALOGPS
logP-4.5ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area383.14 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity200.33 m³·mol⁻¹ChemAxon
Polarizability80.11 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA <> 2-Oxepin-2(3H)-ylideneacetyl-CoA
Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion <> 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
Phenylacetyl-CoA + NADPH + Oxygen > 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water
2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA > 2-Oxepin-2(3H)-ylideneacetyl-CoA
Phenylacetyl-CoA + Hydrogen ion + NADPH + Oxygen > Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
SMPDB Pathways:
Fatty acid metabolismPW000796 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylethylamine metabolismPW002027 ThumbThumb?image type=greyscaleThumb?image type=simple
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW000896 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-1891000210-c192e7c8dfe5230750aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0972000000-ce7ed2b6cc97663f6c69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2950000000-29fdb8afe95e61d377fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3910021222-f2aa242a565924fb01b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900010010-1a6b8de8903bb6f4d24aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-0ef8aae18fd0b83055d1View 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID63458
HMDB IDNot Available
Pubchem Compound ID46926194
Kegg IDC20062
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Probable phenylacetic acid degradation NADH oxidoreductase paaE
General function:
Involved in electron carrier activity
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaE
Uniprot ID:
P76081
Molecular weight:
39320
Protein Details
2. Probable enoyl-CoA hydratase paaF
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaF
Uniprot ID:
P76082
Molecular weight:
27237
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
Protein Details
3. Probable enoyl-CoA hydratase paaG
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaG
Uniprot ID:
P77467
Molecular weight:
28404
Reactions
2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA = 2-oxepin-2(3H)-ylideneacetyl-CoA.
Protein Details
4. Phenylacetic acid degradation protein paaB
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaB
Uniprot ID:
P76078
Molecular weight:
10942
Protein Details
5. Phenylacetic acid degradation protein paaA
General function:
Involved in oxidoreductase activity
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaA
Uniprot ID:
P76077
Molecular weight:
35499
Reactions
Phenylacetyl-CoA + NADPH + O(2) = 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP(+) + H(2)O.
Protein Details
6. Phenylacetic acid degradation protein paaD
General function:
Not Available
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaD
Uniprot ID:
P76080
Molecular weight:
18324
Protein Details
7. Phenylacetic acid degradation protein paaC
General function:
Involved in oxidoreductase activity
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaC
Uniprot ID:
P76079
Molecular weight:
27877