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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:03:23 UTC
HMDB IDHMDB0001166
Secondary Accession Numbers
  • HMDB01166
  • 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
3-Hydroxybutyryl-coenzyme A, (R)-isomerMeSH
3-Hydroxybutyryl-coenzyme A, (S)-isomerMeSH
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 KeyQHHKKMYHDBRONY-JYMPOPDUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as (r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent(R)-3-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
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Biochemical process:

    Chemical reaction:

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-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 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.03 m³·mol⁻¹ChemAxon
Polarizability75.89 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931000130-d924499294c56a627b62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1912000000-416f64a8b75913d6ee9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-137c383401c378170f3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-9720041570-1667d7f76a22ea47025fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910220010-688de5c2366fa2409e73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-7900100000-b81dd46468dec5a6d312View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Saccharopinuria/Hyperlysinemia IIPw000112Pw000112 greyscalePw000112 simpleNot Available
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)Pw000108Pw000108 greyscalePw000108 simpleNot Available
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)Pw000544Pw000544 greyscalePw000544 simpleNot Available
Trifunctional protein deficiencyPw000521Pw000521 greyscalePw000521 simpleNot Available
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)Pw000516Pw000516 greyscalePw000516 simpleNot Available
Displaying entries 16 - 20 of 20 in total
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
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. [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

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