3-Hydroxy-5-oxohexanoyl-CoA (ECMDB20073) (M2MDB000922)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (157)
Record Information
Version2.0
Creation Date2012-05-31 14:26:04 -0600
Update Date2015-09-17 15:41:55 -0600
Secondary Accession Numbers
  • ECMDB20073
Identification
Name:3-Hydroxy-5-oxohexanoyl-CoA
Description3-hydroxy-5-oxohexanoyl-coa belongs to the class of Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-hydroxy-5-oxohexanoyl-coenzyme A
  • Adenosine 3'-phosphate 5'-diphosphate P(2)-2,2-dimethyl-3-hydroxy-3-2-2-(3-hydroxy-5-oxohexanoylthio)ethylaminocarbonylethylaminocarbonylpropyl ester
  • Adenosine 3'-phosphoric acid 5'-diphosphoric acid P(2)-2,2-dimethyl-3-hydroxy-3-2-2-(3-hydroxy-5-oxohexanoylthio)ethylaminocarbonylethylaminocarbonylpropyl ester
  • 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 3-hydroxy-5-oxohexanethioate
  • 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 3-hydroxy-5-oxohexanethioic acid
  • S-{(9R)-1-(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3lambda~5~,5lambda~5~- diphosphaheptadecan-17-yl} 3-hydroxy-5-oxohexanethioate (non-preferred name)
  • S-{(9R)-1-(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3lambda~5~,5lambda~5~- diphosphaheptadecan-17-yl} 3-hydroxy-5-oxohexanethioic acid (non-preferred name)
Chemical Formula:C27H44N7O19P3S
Weight:Average: 895.66
Monoisotopic: 895.162554393
InChI Key:LTOOEXBCTAXFSU-UHFFFAOYSA-N
InChI:InChI=1S/C27H44N7O19P3S/c1-14(35)8-15(36)9-18(38)57-7-6-29-17(37)4-5-30-25(41)22(40)27(2,3)11-50-56(47,48)53-55(45,46)49-10-16-21(52-54(42,43)44)20(39)26(51-16)34-13-33-19-23(28)31-12-32-24(19)34/h12-13,15-16,20-22,26,36,39-40H,4-11H2,1-3H3,(H,29,37)(H,30,41)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)
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-N-[2-({2-[(3-hydroxy-5-oxohexanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-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]-2-hydroxy-N-[2-({2-[(3-hydroxy-5-oxohexanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid
SMILES:CC(=O)CC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-hydroxyacyl 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
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Imidolactam
  • Beta-hydroxy ketone
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Ketone
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Sulfenyl compound
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Organic oxygen 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 Solubility5.63 g/LALOGPS
logP-0.45ALOGPS
logP-5.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area407.91 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.66 m³·mol⁻¹ChemAxon
Polarizability79.83 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Hydroxy-5-oxohexanoate + Acetyl-CoA <> 3-Hydroxy-5-oxohexanoyl-CoA + Acetic acid
Acetyl-CoA + 3-Hydroxy-5-oxohexanoate > Acetic acid + 3-Hydroxy-5-oxohexanoyl-CoA + 3-Hydroxy-5-oxohexanoyl-CoA
SMPDB Pathways:
Aminobenzoate DegradationPW000757 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • 1,4-Dichlorobenzene degradation ec00627
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0971000240-77191bcd8745789a55a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0962000000-9483e55b3755699fcfe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2940000000-6637635931076fd439c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-5910031360-01780ebe8493c16aa045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3910110010-648c47ed308f16983d43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-595ea40e931ef28a0318View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID20052
HMDB IDNot Available
Pubchem Compound ID9543236
Kegg IDC16273
ChemSpider ID7822209
Wikipedia IDNot Available
BioCyc IDCPD-20
EcoCyc IDCPD-20

Enzymes

Protein Details
1. Acetate CoA-transferase subunit alpha
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoD
Uniprot ID:
P76458
Molecular weight:
23526
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
Protein Details
2. Acetate CoA-transferase subunit beta
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoA
Uniprot ID:
P76459
Molecular weight:
22960
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.