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
Description:3-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
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
DescriptionThis compound belongs to the class of chemical entities known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
  • Pentose monosaccharide
  • Organic pyrophosphate
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Pyrimidine
  • 1,3-dicarbonyl compound
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Primary aromatic amine
  • Imidolactam
  • Phosphoric acid ester
  • Alpha-hydrogen aldehyde
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aldehyde
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • 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:
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
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

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.