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Showing metabocard for 3-Hydroxybutyryl-CoA (HMDB0001166)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-25 20:30:32 UTC
HMDB IDHMDB0001166
Secondary Accession Numbers
  • HMDB0002383
  • HMDB01166
  • HMDB02383
Metabolite Identification
Common Name3-Hydroxybutyryl-CoA
Description(R)-3-hydroxybutanoyl-CoA belongs to the class of organic compounds known as (r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative. Thus, (R)-3-hydroxybutanoyl-CoA is considered to be a fatty ester lipid molecule (R)-3-hydroxybutanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1593117032
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3R)-3-Hydroxybutanoyl-CoAChEBI
(R)-3-Hydroxy-butanoyl-CoAHMDB
(R)-3-Hydroxy-butanoyl-coenzyme AHMDB
(R)-3-Hydroxybutyryl CoAHMDB
3-Hydroxybutyryl-CoAHMDB
3-Hydroxybutyryl-coenzyme AHMDB
D-(-)-beta-Hydroxybutyryl-CoAHMDB
D-(-)-beta-Hydroxybutyryl-coenzyme AHMDB
D-(-)-β-Hydroxybutyryl-CoAHMDB
D-(-)-β-Hydroxybutyryl-coenzyme AHMDB
D-3-Hydroxybutyryl-CoAHMDB
D-3-Hydroxybutyryl-coenzyme AHMDB
D-beta-Hydroxybutyryl-CoAHMDB
D-beta-Hydroxybutyryl-coenzyme AHMDB
D-β-Hydroxybutyryl-CoAHMDB
D-β-Hydroxybutyryl-coenzyme AHMDB
R-(-)-3-Hydroxybutyryl-CoAHMDB
R-(-)-3-Hydroxybutyryl-coenzyme AHMDB
beta-Hydroxybutyryl CoAHMDB
beta-Hydroxybutyryl coenzyme AHMDB
β-Hydroxybutyryl CoAHMDB
β-Hydroxybutyryl coenzyme AHMDB
Chemical FormulaC25H42N7O18P3S
Average Molecular Weight853.62
Monoisotopic Molecular Weight853.151989708
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name(R)-3-hydroxybutanoyl-coa
CAS Registry Number21804-29-5
SMILES
C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20+,24-/m1/s1
InChI KeyQHHKKMYHDBRONY-WZZMXTMRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as (r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent(R)-3-hydroxyacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.07 g/LALOGPS
logP-0.62ALOGPS
logP-6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.03 m³·mol⁻¹ChemAxon
Polarizability77.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000140-eba415fd46f47c10a045Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1914000000-aae3b11040f7ee3ffbb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910000000-5c259b64dc19ad3be272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-9720140460-7f9422084aa5ef2f6c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5920120010-46ef6c69443d2b7286e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-5900100000-5010983cc099f69bf8f0Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022460
KNApSAcK IDNot Available
Chemspider ID10140140
KEGG Compound IDC03561
BioCyc IDCPD-650
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID456
PubChem Compound11966146
PDB IDNot Available
ChEBI ID15452
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gerngross TU, Snell KD, Peoples OP, Sinskey AJ, Csuhai E, Masamune S, Stubbe J: Overexpression and purification of the soluble polyhydroxyalkanoate synthase from Alcaligenes eutrophus: evidence for a required posttranslational modification for catalytic activity. Biochemistry. 1994 Aug 9;33(31):9311-20. [PubMed:8049232 ]
  2. Kraak MN, Kessler B, Witholt B: In vitro activities of granule-bound poly[(R)-3-hydroxyalkanoate]polymerase C1 of Pseudomonas oleovorans--development of an activity test for medium-chain-length-poly(3-hydroxyalkanoate) polymerases. Eur J Biochem. 1997 Dec 1;250(2):432-9. [PubMed:9428695 ]
  3. Emmett B, Hochachka PW: Scaling of oxidative and glycolytic enzymes in mammals. Respir Physiol. 1981 Sep;45(3):261-72. [PubMed:7036306 ]

Enzymes

Enzyme Details
1. Peroxisomal bifunctional enzyme
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
3-Hydroxybutyryl-CoA + NAD → Acetoacetyl-CoA + NADH + Hydrogen Iondetails
3-Hydroxybutyryl-CoA → Crotonoyl-CoA + Waterdetails
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails
Enzyme Details
2. Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:
HADH
Uniprot ID:
Q16836
Molecular weight:
36035.11
Reactions
3-Hydroxybutyryl-CoA + NAD → Acetoacetyl-CoA + NADH + Hydrogen Iondetails
Enzyme Details
3. Enoyl-CoA hydratase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:
ECHS1
Uniprot ID:
P30084
Molecular weight:
31387.085
Reactions
3-Hydroxybutyryl-CoA → Crotonoyl-CoA + Waterdetails
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails
Enzyme Details
4. Trifunctional enzyme subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
3-Hydroxybutyryl-CoA → Crotonoyl-CoA + Waterdetails
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails