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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 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
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+204.17930932474
DeepCCS[M-H]-202.52630932474
DeepCCS[M-2H]-236.5630932474
DeepCCS[M+Na]+210.33630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxybutyryl-CoAC[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=C2N5803.6Standard polar33892256
3-Hydroxybutyryl-CoAC[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=C2N4292.7Standard non polar33892256
3-Hydroxybutyryl-CoAC[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=C2N6560.4Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Positive-QTOFsplash10-000i-1912000140-eba415fd46f47c10a0452019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Positive-QTOFsplash10-000i-1914000000-aae3b11040f7ee3ffbb42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Positive-QTOFsplash10-000i-1910000000-5c259b64dc19ad3be2722019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Negative-QTOFsplash10-053r-9720140460-7f9422084aa5ef2f6c4e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Negative-QTOFsplash10-001i-5920120010-46ef6c69443d2b7286e22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Negative-QTOFsplash10-0a7i-5900100000-5010983cc099f69bf8f02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Negative-QTOFsplash10-0udi-0000000190-d473b36a9239d68c39682021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Negative-QTOFsplash10-0fv0-7500104960-d5a9b05839a7099bb9c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Negative-QTOFsplash10-0fvs-6002504910-fcc4f9405d0cdb56506c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 10V, Positive-QTOFsplash10-0udi-0000000190-10a5a939008a51384a4d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 20V, Positive-QTOFsplash10-000i-0901001470-a6ff0d6eff5b7a93c01a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxybutyryl-CoA 40V, Positive-QTOFsplash10-0002-0029000000-3cbf971409e55f5f2d9b2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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

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
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 → Crotonoyl-CoA + Waterdetails
Crotonoyl-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 → Crotonoyl-CoA + Waterdetails
Crotonoyl-CoA + Water → 3-Hydroxybutyryl-CoAdetails