Butyryl-CoA (ECMDB01088) (M2MDB000250)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (10)XML
Proteins (2084)
Record Information
Version2.0
Creation Date2012-05-31 13:45:00 -0600
Update Date2015-09-17 15:41:08 -0600
Secondary Accession Numbers
  • ECMDB01088
Identification
Name:Butyryl-CoA
DescriptionButyryl-CoA is a member of the chemical class known as Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond. Butyryl-coenzyme A (or butyryl-CoA) is the coenzyme A-activated form of butyric acid. (WikiPedia)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Butanoyl-CoA
  • Butanoyl-Coenzyme A
  • Butyryl-CoA
  • Butyryl-coenzyme A
Chemical Formula:C25H42N7O17P3S
Weight:Average: 837.624
Monoisotopic: 837.157073179
InChI Key:CRFNGMNYKDXRTN-UHFFFAOYSA-N
InChI:InChI=1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)
CAS number:2140-48-9
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)-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-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]-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid
SMILES:CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Ergostane-skeleton
  • Ecdysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • 3-hydroxysteroid
  • 6-oxosteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.01 g/LALOGPS
logP-0.22ALOGPS
logP-4.5ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity182.48 m³·mol⁻¹ChemAxon
Polarizability75.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Acetyl-CoA + Butyric acid > Acetic acid + Butyryl-CoA
Acetyl-CoA + Butyryl-CoA <> 3-Oxohexanoyl-CoA + Coenzyme A
Butyryl-CoA + FAD <> Crotonoyl-CoA + FADH2
Butyryl-CoA + electron-transfer flavoprotein + Butyryl-CoA <> Crotonoyl-CoA + Reduced electron-transfer flavoprotein
Acetyl-CoA + Butyryl-CoA + Butyryl-CoA > 3-Oxohexanoyl-CoA + Coenzyme A
Butyric acid + Coenzyme A + Adenosine triphosphate > Adenosine triphosphate + Butyryl-CoA + Butyryl-CoA
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (Butanoate)PW001017 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Phenylalanine metabolism ec00360
  • Valine, leucine and isoleucine degradation ec00280
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-017i-7930142460-c2298a969e995ad3d00aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910100010-7599cb988facd52223daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-f5f10442ccac27dc38ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-073f428b330788172433View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-9200102230-8569a6d934e6ef361838View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-4003402900-aa858b6cf989ef7545e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1931000110-da1db28a855c878b4aedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1921000000-5675ad3c288d42128697View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ks-2910000000-64ab778c97047046a2d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000190-722be0a11d66c5eb058cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911001570-3a8be9989cbf457b7031View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0019000000-35adb55601f58e5ce0acView 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 ID15479
HMDB IDHMDB01088
Pubchem Compound IDNot Available
Kegg IDC00136
ChemSpider ID109043
WikipediaButyryl-CoA
BioCyc IDBUTYRYL-COA
EcoCyc IDBUTYRYL-COA

Enzymes

Protein Details
1. Aldehyde-alcohol dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme has three activities:ADH, ACDH, and PFL- deactivase. In aerobic conditions it acts as a hydrogen peroxide scavenger. The PFL deactivase activity catalyzes the quenching of the pyruvate-formate-lyase catalyst in an iron, NAD, and CoA dependent reaction
Gene Name:
adhE
Uniprot ID:
P0A9Q7
Molecular weight:
96126
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH.
Protein Details
2. 3-ketoacyl-CoA thiolase
General function:
Involved in acetyl-CoA C-acyltransferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadA
Uniprot ID:
P21151
Molecular weight:
40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
Protein Details
3. Acetate CoA-transferase subunit alpha
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoD
Uniprot ID:
P76458
Molecular weight:
23526
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
Protein Details
4. Acetate CoA-transferase subunit beta
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoA
Uniprot ID:
P76459
Molecular weight:
22960
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
Protein Details
5. Acetyl-CoA acetyltransferase
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
2 acetyl-CoA = CoA + acetoacetyl-CoA
Gene Name:
atoB
Uniprot ID:
P76461
Molecular weight:
40352
Reactions
2 acetyl-CoA = CoA + acetoacetyl-CoA.
Protein Details
6. 3-ketoacyl-CoA thiolase_
General function:
Involved in transferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. 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:
fadI
Uniprot ID:
P76503
Molecular weight:
46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
Protein Details
7. Acetaldehyde dehydrogenase
General function:
Involved in acetaldehyde dehydrogenase (acetylating) activity
Specific function:
Catalyzes the conversion of acetaldehyde to acetyl-CoA, using NAD(+) and coenzyme A. Is the final enzyme in the meta- cleavage pathway for the degradation of 3-phenylpropanoate. Functions as a chaperone protein for folding of mhpE
Gene Name:
mhpF
Uniprot ID:
P77580
Molecular weight:
33442
Reactions
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH.
Protein Details
8. Probable acetyl-CoA acetyltransferase
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
2 acetyl-CoA = CoA + acetoacetyl-CoA
Gene Name:
yqeF
Uniprot ID:
Q46939
Molecular weight:
41018
Reactions
2 acetyl-CoA = CoA + acetoacetyl-CoA.
Protein Details
9. Acyl-coenzyme A dehydrogenase
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the dehydrogenation of acyl-CoA
Gene Name:
fadE
Uniprot ID:
Q47146
Molecular weight:
89224
Reactions
An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).
Protein Details
10. Short-chain-fatty-acid--CoA ligase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It has a low activity on medium or long chain fatty acids and is maximally active on C6 and C8 substrates
Gene Name:
fadK
Uniprot ID:
P38135
Molecular weight:
60773
Reactions
ATP + a short-chain carboxylic acid + CoA = AMP + diphosphate + an acyl-CoA.