Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000280
Identification
Name: 3-Hydroxybutyryl-CoA
Description:3-Hydroxybutyryl-CoA or 3-hydroxybutyryl-coenzyme A is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan.
Structure
Thumb
Synonyms:
  • β-hydroxybutyryl-S-CoA
  • β-hydroxybutyryl-CoA
  • β-hydroxybutyryl-s-CoA
  • (3R)-3-Hydroxybutanoyl-CoA
  • (3R)-3-Hydroxybutanoyl-Coenzyme A
  • (R)-3-Hydroxybutanoyl-CoA
  • (R)-3-Hydroxybutanoyl-Coenzyme A
  • (S)-3-hydroxybutanoyl-CoA
  • (S)-3-hydroxybutanoyl-Coenzyme A
  • 3-Hydroxybutanoyl-CoA
  • 3-Hydroxybutanoyl-coenzyme a
  • 3-Hydroxybutyryl-CoA
  • 3-Hydroxybutyryl-coenzyme A
  • 3-OH-butyryl-CoA
  • 3-OH-butyryl-Coenzyme A
  • b-Hydroxybutyryl-CoA
  • b-Hydroxybutyryl-coenzyme A
  • b-Hydroxybutyryl-S-CoA
  • b-Hydroxybutyryl-S-coenzyme A
  • Beta-Hydroxybutyryl-CoA
  • Beta-Hydroxybutyryl-Coenzyme A
  • Beta-Hydroxybutyryl-S-CoA
  • Beta-Hydroxybutyryl-S-Coenzyme A
  • D-3-Hydroxybutyryl-CoA
  • Hydroxy-butyryl-CoA
  • Hydroxy-butyryl-Coenzyme A
  • OH-butyryl-CoA
  • β-Hydroxybutyryl-CoA
  • β-Hydroxybutyryl-coenzyme A
  • β-Hydroxybutyryl-S-CoA
  • β-Hydroxybutyryl-S-coenzyme A
Chemical Formula: C25H42N7O18P3S
Average Molecular Weight: 853.623
Monoisotopic Molecular Weight: 853.151987801
InChI Key: QHHKKMYHDBRONY-JYMPOPDUSA-N
InChI: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
CAS number: 2871-66-1
IUPAC Name:(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
Traditional IUPAC Name: (2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-{2-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
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
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent Acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • 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
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.13 mg/mLALOGPS
logP-0.49ALOGPS
logP-5.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area390.84 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity184.07 m3·mol-1ChemAxon
Polarizability75.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931000130-23f3e172cccb46516046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1912000000-399c515245dec6a2cc71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1920000000-8fe1c131ac5ed900f9eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-9720051570-ac103b1d89e177e590b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910120010-ac00f635f518b7677a1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-5fd723fafb9eda8bd257View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15452
HMDB IDHMDB01166
Pubchem Compound ID521
Kegg IDC01144
ChemSpider ID389056
Wikipediabeta-hydroxybutyryl-CoA
BioCyc IDCPD-650
EcoCyc IDCPD-650
Ligand Expo3HC