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(S)-3-Hydroxybutanoyl-CoA (M2MDB002036)

Record Information
Version2.0
Creation Date2012-08-15 08:51:29 -0600
Update Date2015-06-03 17:21:59 -0600
Secondary Accession Numbers
  • ECMDB21642
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
MOLSDFPDBSMILESInChI
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
Weight:Average: 853.623
Monoisotopic: 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,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:(S)-3-hydroxybutanoyl-coa
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
Description belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent(S)-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
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.13 g/LALOGPS
logP-0.49ALOGPS
logP-6ChemAxon
logS-2.1ALOGPS
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
Polarizability77.21 ųChemAxon
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
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000190-d4aa33b196af72ac06cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-1301102790-5031f947450e97f8dc8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0039000000-2c32496eb9d5b677d278View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000190-8fba08e29a0129c20131View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gu-9500106840-70232b0f4b23ef5ffa0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fms-9000422600-94c159b363bfe9e117f6View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15453
HMDB IDHMDB0303997
Pubchem Compound ID439419
Kegg IDC01144
ChemSpider ID388532
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand Expo3HC

Enzymes

Protein Details
1. Fatty acid oxidation complex subunit alpha
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.
Protein Details
2. Probable enoyl-CoA hydratase paaF
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaF
Uniprot ID:
P76082
Molecular weight:
27237
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
Protein Details
3. Probable 3-hydroxybutyryl-CoA dehydrogenase
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3- acetoacetyl-CoA + NADPH
Gene Name:
paaH
Uniprot ID:
P76083
Molecular weight:
51732
Reactions
(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3-acetoacetyl-CoA + NADPH.
Protein Details
4. Fatty acid oxidation complex subunit alpha_
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:
fadJ
Uniprot ID:
P77399
Molecular weight:
77072
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Transporters

Protein Details
1. Fatty acid oxidation complex subunit alpha
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.