3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde (ECMDB23158) (M2MDB003548)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (30)
Record Information
Version2.0
Creation Date2012-10-10 12:19:33 -0600
Update Date2015-06-03 17:26:03 -0600
Secondary Accession Numbers
  • ECMDB23158
Identification
Name:3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
Description3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde is an intermediate in phenylacetate metabolism. It is a substrate for the enzyme known as Bifunctional protein PaaZ. This enzyme consists of a C-terminal (R)-specific enoyl-CoA hydratase domain (formerly MaoC) that cleaves the phenylacetate ring and produces the highly reactive 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde and an N-terminal NADP-dependent aldehyde dehydrogenase domain that oxidizes the aldehyde to 3-oxo-5,6-dehydrosuberyl-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 (Z)-3,8-dioxooct-5-enethioate
  • 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 (Z)-3,8-dioxooct-5-enethioic acid
Chemical Formula:C29H44N7O19P3S
Weight:Average: 919.681
Monoisotopic: 919.162552487
InChI Key:XYGQIZWAZKPGNV-ZVEAYUPDSA-N
InChI:InChI=1S/C29H44N7O19P3S/c1-29(2,24(42)27(43)32-8-7-19(39)31-9-11-59-20(40)12-17(38)6-4-3-5-10-37)14-52-58(49,50)55-57(47,48)51-13-18-23(54-56(44,45)46)22(41)28(53-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-4,10,15-16,18,22-24,28,41-42H,5-9,11-14H2,1-2H3,(H,31,39)(H,32,43)(H,47,48)(H,49,50)(H2,30,33,34)(H2,44,45,46)/b4-3-/t18-,22-,23-,24+,28-/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)-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic 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]-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid
SMILES:O=CC\C([H])=C(\[H])CC(=O)CC(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-oxo-acyl 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
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • 1,3-dicarbonyl compound
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • N-acyl-amine
  • Alkyl phosphate
  • Pyrimidine
  • Imidolactam
  • Fatty amide
  • Monosaccharide
  • Phosphoric acid ester
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Alpha-hydrogen aldehyde
  • Tetrahydrofuran
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Ketone
  • Carbothioic s-ester
  • Sulfenyl compound
  • Oxacycle
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Alcohol
  • Aldehyde
  • Organic oxide
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.04 g/LALOGPS
logP0.38ALOGPS
logP-4.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area404.75 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity203.43 m³·mol⁻¹ChemAxon
Polarizability82.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-Oxepin-2(3H)-ylideneacetyl-CoA + Water <> 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
2-Oxepin-2(3H)-ylideneacetyl-CoA + Water > 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + Water + NADP > Hydrogen ion + NADPH + 3-Oxo-5,6-dehydrosuberyl-CoA
SMPDB Pathways:
Collection of Reactions without pathwaysPW001891 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
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1891000202-f3ea3758b79139203398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-1980100000-e9cc2354ce03c72c2a19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2950000000-c5adaa148e728c314fbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1030-2911021214-5769504ace3c2360ef14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2910110001-430e565c8cfda0a74027View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-d8acd61364b7aaf8bcefView in MoNA
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 IDNot Available
HMDB IDNot Available
Pubchem Compound ID56928138
Kegg IDC19946
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Protein maoC
General function:
Involved in oxidoreductase activity
Specific function:
Specific function unknown
Gene Name:
maoC
Uniprot ID:
P77455
Molecular weight:
73002
Reactions
2-oxepin-2(3H)-ylideneacetyl-CoA + H(2)O = 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde.
3-oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP(+) + H(2)O = 3-oxo-5,6-dehydrosuberyl-CoA + NADPH.