Record Information
Version1.0
Creation date2011-09-21 00:13:19 UTC
Update date2015-07-21 06:57:11 UTC
Primary IDFDB022393
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-3-Hydroxyisobutyryl-CoA
Description(S)-3-Hydroxyisobutyryl-CoA is s metabolite of 3-hydroxyisobutyryl-CoA hydrolase (EC 3.1.2.4 ) during beta-alanine metabolism (KEGG 00410), propanoate metabolism (KEGG 00640), and valine, leucine and isoleucine degradation (KEGG 00280). Deficiencies of this enzyme in valine degradation can result in hypotonia, poor feeding, motor delay, and subsequent neurological regression in infancy, episodes of ketoacidosis and Leigh-like changes in the basal ganglia on a magnetic resonance imaging scan (PMID 17160907). [HMDB]
CAS Number319440-43-2
Structure
Thumb
Synonyms
SynonymSource
(S)-3-Hydroxyisobutyryl-coenzyme AHMDB
3-Hydroxy-2-methylpropanoyl-CoAHMDB
3-Hydroxy-2-methylpropanoyl-coenzyme AHMDB
3-Hydroxy-2-methylpropionyl-CoAHMDB
3-Hydroxy-2-methylpropionyl-coenzyme AHMDB
3-Hydroxy-isobutyryl-CoAHMDB
3-Hydroxy-isobutyryl-coenzyme AHMDB
3-Hydroxyisobutyryl-CoAHMDB
3-Hydroxyisobutyryl-coenzyme AHMDB
(S)-3-Hydroxyisobutyryl-CoAhmdb
(S)-3-Hydroxyisobutyryl-Coenzyme Ahmdb
3-Hydroxy-2-methylpropanoyl-Coenzyme Ahmdb
3-Hydroxy-2-methylpropionyl-Coenzyme Ahmdb
3-hydroxy-isobutyryl-CoAhmdb
3-hydroxy-isobutyryl-coenzyme Ahmdb
3-hydroxyisobutyryl-CoAhmdb
3-hydroxyisobutyryl-Coenzyme Ahmdb
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
Chemical FormulaC25H42N7O18P3S
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
InChI IdentifierInChI=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)
InChI KeyWWEOGFZEFHPUAM-UHFFFAOYSA-N
Isomeric SMILESCC(CO)C(=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=C(N)N=CN=C12
Average Molecular Weight853.623
Monoisotopic Molecular Weight853.151987801
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000120-c718f8aabcd5b3328193View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-86eb8b4e6cdee60b559aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-2d6f48b3506835c89ffdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o9-9730140560-056ac34ed9b661751c57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3920110010-37a68eba22e3eecc9757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-e33bac5e5de19c7b719bView in MoNA
ChemSpider ID86
ChEMBL IDNot Available
KEGG Compound IDC06000
Pubchem Compound ID88
Pubchem Substance IDNot Available
ChEBI ID28259
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01052
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID47176
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-hydroxyisobutyryl-CoA hydrolase, mitochondrialHIBCHQ6NVY1
Enoyl-CoA hydratase, mitochondrialECHS1P30084
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference