Record Information
Version1.0
Creation date2011-09-21 00:14:22 UTC
Update date2015-07-21 06:57:13 UTC
Primary IDFDB022460
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Hydroxybutyryl-CoA
Description3-Hydroxybutyryl-CoA, also known as 3-hydroxybutanoyl-CoA or 3-OH-butyryl-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. 3-Hydroxybutyryl-CoA is a strong basic compound (based on its pKa).
CAS Number2871-66-1
Structure
Thumb
Synonyms
SynonymSource
(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)-isomerHMDB
3-Hydroxybutyryl-coenzyme A, (S)-isomerHMDB
(3R)-3-Hydroxybutanoyl-Coenzyme Ahmdb
(R)-3-Hydroxybutanoyl-Coenzyme Ahmdb
(S)-3-hydroxybutanoyl-CoAhmdb
(S)-3-hydroxybutanoyl-Coenzyme Ahmdb
3-hydroxybutanoyl-CoAhmdb
3-hydroxybutanoyl-coenzyme ahmdb
3-hydroxybutyryl-CoAhmdb
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
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
Chemical FormulaC25H42N7O18P3S
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
InChI IdentifierInChI=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
Isomeric SMILESC[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
Average Molecular Weight853.623
Monoisotopic Molecular Weight853.151987801
Classification
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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-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
ChemSpider ID389056
ChEMBL IDNot Available
KEGG Compound IDC03561
Pubchem Compound ID440045
Pubchem Substance IDNot Available
ChEBI ID15452
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01166
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36912
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDbeta-hydroxybutyryl-CoA
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
Enoyl-CoA hydratase, mitochondrialECHS1P30084
Pathways
NameSMPDB LinkKEGG Link
Butyrate MetabolismSMP00073 map00650
Fatty acid MetabolismSMP00051 map00071
Lysine DegradationSMP00037 map00310
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference