(S)-3-Hydroxybutanoyl-CoA (PAMDB002036)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB002036
Identification
Name: (S)-3-Hydroxybutanoyl-CoA
Description:(S)-3-hydroxybutanoyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (3S)-3-hydroxybutanoyl-CoA
  • (S)-3-Hydroxybutanoyl-CoA
  • (S)-3-hydroxybutyroyl-CoA
  • (S)-3-hydroxybutyryl-coa
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-4-({3-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-4-({3-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphoric acid}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-4-({3-[(2-{[(3S)-3-hydroxybutanoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-4-({3-[(2-{[(3S)-3-hydroxybutanoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphoric acid}
  • 3-HYDROXYBUTANOYL-COENZYME A
  • L(+)-3-Hydroxybutyroyl-CoA
  • L(+)-b-Hydroxybutyroyl-CoA
  • L(+)-beta-Hydroxybutyroyl-CoA
  • L(+)-β-Hydroxybutyroyl-CoA
  • L-3-Hydroxybutanoyl-CoA
Chemical Formula: C25H42N7O18P3S
Average Molecular Weight: 853.623
Monoisotopic Molecular Weight: 853.151987801
InChI Key: QHHKKMYHDBRONY-VKBDFPRVSA-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+/m0/s1
CAS number: Not Available
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:[H][C@@](C)(O)CC(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
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: Not Available
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:
(S)-3-Hydroxybutanoyl-CoA + NAD <> Acetoacetyl-CoA + NADH + Hydrogen ion
(S)-3-Hydroxybutanoyl-CoA + NADP + 3-Hydroxybutyryl-CoA <> Acetoacetyl-CoA + NADPH + Hydrogen ion
(S)-3-Hydroxybutanoyl-CoA <> Crotonoyl-CoA + Water
(S)-3-Hydroxybutanoyl-CoA <> 3-Hydroxybutyryl-CoA
Pathways: Not Available
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: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15453
HMDB IDNot Available
Pubchem Compound ID439419
Kegg IDC01144
ChemSpider ID388532
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand Expo3HC