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(S)-3-Hydroxyisobutyryl-CoA (YMDB00053)

Identification
YMDB IDYMDB00053
Name(S)-3-Hydroxyisobutyryl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-3-Hydroxyisobutyryl-CoA, also known as 3-hydroxy-isobutyryl-coenzyme A or 3-hydroxy-2-methylpropanoyl-CoA, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core (S)-3-Hydroxyisobutyryl-CoA is a strong basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (S)-3-Hydroxyisobutyryl-CoA
  • (S)-3-Hydroxyisobutyryl-Coenzyme A
  • 3-Hydroxy-2-methylpropanoyl-CoA
  • 3-Hydroxy-2-methylpropanoyl-Coenzyme A
  • 3-Hydroxy-2-methylpropionyl-CoA
  • 3-Hydroxy-2-methylpropionyl-Coenzyme A
  • 3-hydroxy-isobutyryl-CoA
  • 3-hydroxy-isobutyryl-coenzyme A
  • 3-hydroxyisobutyryl-CoA
  • 3-hydroxyisobutyryl-Coenzyme A
CAS number319440-43-2
WeightAverage: 853.623
Monoisotopic: 853.151987801
InChI KeyWWEOGFZEFHPUAM-UHFFFAOYSA-N
InChIInChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name[5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
Chemical FormulaC25H42N7O18P3S
SMILES[H]OC([H])([H])C([H])(C(=O)SC([H])([H])C([H])([H])N([H])C(=O)C([H])([H])C([H])([H])N([H])C(=O)C([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])C1([H])OC([H])(N2C([H])=NC3=C2N=C([H])N=C3N([H])[H])C([H])(O[H])C1([H])OP(=O)(O[H])O[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.14 g/LALOGPS
logP-0.56ALOGPS
logP-7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.18 m³·mol⁻¹ChemAxon
Polarizability74.9 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Valine, leucine and isoleucine degradationec00280 Map00280
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000120-c718f8aabcd5b3328193JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-86eb8b4e6cdee60b559aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-2d6f48b3506835c89ffdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o9-9730140560-056ac34ed9b661751c57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3920110010-37a68eba22e3eecc9757JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-e33bac5e5de19c7b719bJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Hawes, John W.; Harper, Edwin T. Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA. Methods in Enzymology (2000), 324(Branched-Chain Amino Acids), 73-79.
External Links:
ResourceLink
CHEBI ID28259
HMDB IDHMDB01052
Pubchem Compound ID88
Kegg IDC06000
ChemSpider ID86
FOODB IDFDB022393
Wikipedia IDNot Available
BioCyc ID3-HYDROXY-ISOBUTYRYL-COA

Enzymes

Protein Details
1. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA. Has an indirect role in endocytic membrane trafficking. May have a function in protein biosynthesis in mitochondrial small ribosomal subunit
Gene Name:
EHD3
Uniprot ID:
P28817
Molecular weight:
56287.89844
Reactions
3-hydroxy-2-methylpropanoyl-CoA + H(2)O → CoA + 3-hydroxy-2-methylpropanoate.