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
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:
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
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

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
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.
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.
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
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.
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
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