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Record Information
Version	2.0
Creation Date	2012-07-30 14:54:45 -0600
Update Date	2015-06-03 17:20:48 -0600
Secondary Accession Numbers	ECMDB21172
Identification
Name:	3-Oxo-5,6-dehydrosuberyl-CoA
Description	3-Oxo-5,6-dehydrosuberyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8a5fbbc8> Close
Synonyms:	(5Z)-7-carboxy-3-oxohept-5-enoyl-CoA (5Z)-7-carboxy-3-oxohept-5-enoyl-CoA
Chemical Formula:	C29H44N7O20P3S
Weight:	Average: 935.681 Monoisotopic: 935.157467109
InChI Key:	IFFFDKYRRUVOFP-NOQDIWQESA-N
InChI:	InChI=1S/C29H44N7O20P3S/c1-29(2,24(43)27(44)32-8-7-18(38)31-9-10-60-20(41)11-16(37)5-3-4-6-19(39)40)13-53-59(50,51)56-58(48,49)52-12-17-23(55-57(45,46)47)22(42)28(54-17)36-15-35-21-25(30)33-14-34-26(21)36/h3-4,14-15,17,22-24,28,42-43H,5-13H2,1-2H3,(H,31,38)(H,32,44)(H,39,40)(H,48,49)(H,50,51)(H2,30,33,34)(H2,45,46,47)/t17-,22-,23-,24+,28-/m1/s1
CAS number:	Not Available
IUPAC Name:	8-({2-[(3-{[(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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-6,8-dioxooct-3-enoic acid
Traditional IUPAC Name:	8-({2-[(3-{[(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]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-6,8-dioxooct-3-enoic acid
SMILES:	[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC(=O)CC=CCC(O)=O)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 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	3-oxo-acyl CoAs
Alternative Parents	2,3,4-saturated fatty acyl CoAs Medium-chain fatty acyl CoAs Coenzyme A and derivatives Purine ribonucleoside diphosphates Pentose phosphates Ribonucleoside 3'-phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Organic pyrophosphates Monosaccharide phosphates Medium-chain fatty acids Aminopyrimidines and derivatives Hydroxy fatty acids Monoalkyl phosphates Unsaturated fatty acids 1,3-dicarbonyl compounds N-substituted imidazoles N-acyl amines Imidolactams Heteroaromatic compounds Tetrahydrofurans Secondary carboxylic acid amides Secondary alcohols Amino acids Carbothioic S-esters Thioesters Ketones Carboxylic acids Sulfenyl compounds Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Primary amines Organopnictogen compounds Organic oxides Hydrocarbon derivatives
Substituents	Coenzyme a or derivatives Purine ribonucleoside diphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside 3',5'-bisphosphate Ribonucleoside 3'-phosphate Pentose-5-phosphate Pentose phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Pentose monosaccharide Organic pyrophosphate Monosaccharide phosphate Purine Imidazopyrimidine Medium-chain fatty acid Aminopyrimidine Hydroxy fatty acid Monoalkyl phosphate 1,3-dicarbonyl compound Unsaturated fatty acid Fatty amide Monosaccharide N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Fatty acid Phosphoric acid ester Imidolactam Alkyl phosphate Pyrimidine Tetrahydrofuran Imidazole Azole Heteroaromatic compound Carboxamide group Thiocarboxylic acid ester Amino acid Carbothioic s-ester Secondary carboxylic acid amide Secondary alcohol Ketone Amino acid or derivatives Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Oxacycle Thiocarboxylic acid or derivatives Azacycle Organoheterocyclic compound Sulfenyl compound Organic oxygen compound Organopnictogen compound Carbonyl group Primary amine Organic oxide Alcohol Amine Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organooxygen compound Organosulfur compound Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	acyl-CoA (CHEBI:63253 )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.46 g/L ALOGPS logP 0.05 ALOGPS logP -3.7 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 0.82 ChemAxon pKa (Strongest Basic) 4.83 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 22 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 424.98 Ų ChemAxon Rotatable Bond Count 26 ChemAxon Refractivity 204.36 m³·mol⁻¹ ChemAxon Polarizability 83.17 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <> 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA 2-Oxepin-2(3H)-ylideneacetyl-CoA + 2 Water + NADP > 3-Oxo-5,6-dehydrosuberyl-CoA +2 Hydrogen ion + NADPH 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water <> 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion 2-Oxepin-2(3H)-ylideneacetyl-CoA + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A > 2,3-dehydroadipyl-CoA + Acetyl-CoA 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion 2,3-dehydroadipyl-CoA + Acetyl-CoA > CoA + 3-Oxo-5,6-dehydrosuberyl-CoA 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 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A > Acetyl-CoA + 2,3-didehydroadipyl-CoA 3 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <>5 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA 3 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <>5 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA
SMPDB Pathways:	Phenylalanine metabolism PW000921 Phenylethylamine metabolism PW002027
KEGG Pathways:	Benzoate degradation via hydroxylation ec00362 Phenylalanine metabolism ec00360
EcoCyc Pathways:	phenylacetate degradation I (aerobic) PWY0-321
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kr-1964100305-916fd72811157d17a619 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000l-0952200000-f4eb0e1814a70fa1fd8c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-2931000000-bfb30f7e8ad78dce09cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00lr-2911031315-3a6fab8577fcd8a04590 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-2910110001-797d85c7274c9134f1fb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900000000-135442d87faa29036185 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 63253 HMDB ID Not Available Pubchem Compound ID 56927776 Kegg ID C19945 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-2364 EcoCyc ID CPD0-2364

Enzymes