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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-05-13 21:33:06 UTC
HMDB IDHMDB01166
Secondary Accession Numbers
  • HMDB02383
Metabolite Identification
Common Name3-Hydroxybutyryl-CoA
Description3-Hydroxybutyryl-CoA is a substrate for Enoyl-CoA hydratase (mitochondrial), Trifunctional enzyme alpha subunit (mitochondrial) and Peroxisomal bifunctional enzyme.
Structure
Thumb
Synonyms
ValueSource
(3R)-3-Hydroxybutanoyl-CoAHMDB
(3R)-3-Hydroxybutanoyl-coenzyme AHMDB
(R)-3-Hydroxybutanoyl-CoAHMDB
(R)-3-Hydroxybutanoyl-coenzyme AHMDB
(S)-3-Hydroxybutanoyl-CoAHMDB
(S)-3-Hydroxybutanoyl-coenzyme AHMDB
3-Hydroxybutanoyl-CoAHMDB
3-Hydroxybutanoyl-coenzyme AHMDB
3-Hydroxybutyryl-coenzyme AHMDB
3-OH-Butyryl-CoAHMDB
3-OH-Butyryl-coenzyme AHMDB
beta-Hydroxybutyryl-CoAHMDB
beta-Hydroxybutyryl-coenzyme AHMDB
beta-Hydroxybutyryl-S-CoAHMDB
beta-Hydroxybutyryl-S-coenzyme AHMDB
Hydroxy-butyryl-CoAHMDB
Hydroxy-butyryl-coenzyme AHMDB
Chemical FormulaC25H42N7O18P3S
Average Molecular Weight853.623
Monoisotopic Molecular Weight853.151987801
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[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[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number2871-66-1
SMILES
C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(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 KeyInChIKey=QHHKKMYHDBRONY-JYMPOPDUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
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 mg/mLALOGPS
logP-0.62ALOGPS
logP-7.1ChemAxon
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 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.03 m3·mol-1ChemAxon
Polarizability75.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
2-aminoadipic 2-oxoadipic aciduriaSMP00719Not Available
Butyrate MetabolismSMP00073map00650
Carnitine palmitoyl transferase deficiency (I)SMP00538Not Available
Carnitine palmitoyl transferase deficiency (II)SMP00541Not Available
Ethylmalonic EncephalopathySMP00181Not Available
Fatty acid MetabolismSMP00051map00071
Glutaric Aciduria Type ISMP00185Not Available
Glutaric Aciduria Type ISMP00186Not Available
Hyperlysinemia I, FamilialSMP00527Not Available
Hyperlysinemia II or SaccharopinuriaSMP00528Not Available
Long chain acyl-CoA dehydrogenase deficiency (LCAD)SMP00539Not Available
Lysine DegradationSMP00037map00310
Medium chain acyl-coa dehydrogenase deficiency (MCAD)SMP00542Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480Not Available
Pyridoxine dependency with seizuresSMP00571Not Available
Saccharopinuria/Hyperlysinemia IISMP00239Not Available
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)SMP00235Not Available
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)SMP00568Not Available
Trifunctional protein deficiencySMP00545Not Available
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)SMP00540Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022460
KNApSAcK IDNot Available
Chemspider ID389056
KEGG Compound IDC03561
BioCyc IDCPD-650
BiGG ID36912
Wikipedia Linkbeta-hydroxybutyryl-CoA
NuGOwiki LinkHMDB01166
Metagene LinkHMDB01166
METLIN ID456
PubChem Compound440045
PDB IDNot Available
ChEBI ID15452
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. [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. [9428695 ]
  3. Emmett B, Hochachka PW: Scaling of oxidative and glycolytic enzymes in mammals. Respir Physiol. 1981 Sep;45(3):261-72. [7036306 ]

Enzymes

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 → (E)-but-2-enoyl-CoA + Waterdetails
(E)-but-2-enoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails
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
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 → (E)-but-2-enoyl-CoA + Waterdetails
(E)-but-2-enoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
3-Hydroxybutyryl-CoA → (E)-but-2-enoyl-CoA + Waterdetails
(E)-but-2-enoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails