Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 08:34:48 UTC
Update Date2021-09-24 08:34:48 UTC
HMDB IDHMDB0304279
Secondary Accession NumbersNone
Metabolite Identification
Common Namebutanoyl-CoA
DescriptionButyryl-coa, also known as 4:0-coa or butanoyl-coa, is a member of the class of compounds known as acyl coas. Acyl coas are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, butyryl-coa is considered to be a fatty ester lipid molecule. Butyryl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Butyryl-coa can be synthesized from coenzyme A and butyric acid. Butyryl-coa is also a parent compound for other transformation products, including but not limited to, (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA, acetoacetyl-CoA, and 2-methylacetoacetyl-CoA. Butyryl-coa can be found in a number of food items such as wild carrot, persian lime, redcurrant, and arrowroot, which makes butyryl-coa a potential biomarker for the consumption of these food products. Butyryl-coa may be a unique E.coli metabolite.
Structure
Thumb
Synonyms
ValueSource
4:0-CoAChEBI
Butanoyl-CoAChEBI
Butanoyl-coenzyme AChEBI
Butyryl-coenzyme AChEBI
C4:0-CoAChEBI
coenzyme A, S-ButanoateChEBI
S-Butanoyl-CoAChEBI
S-Butanoyl-coenzyme AChEBI
S-Butyryl-CoAChEBI
S-Butyryl-coenzym-aChEBI
S-Butyryl-coenzyme AChEBI
coenzyme A, S-Butanoic acidGenerator
Butyryl-CoAMeSH, KEGG
Chemical FormulaC25H42N7O17P3S
Average Molecular Weight837.624
Monoisotopic Molecular Weight837.157073179
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 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
CAS Registry NumberNot Available
SMILES
CCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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
InChI Identifier
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)/t14-,18-,19-,20+,24-/m1/s1
InChI KeyCRFNGMNYKDXRTN-CITAKDKDSA-N
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
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+255.70732859911
AllCCS[M+H-H2O]+256.07132859911
AllCCS[M+Na]+255.19932859911
AllCCS[M+NH4]+255.3232859911
AllCCS[M-H]-250.62632859911
AllCCS[M+Na-2H]-254.73232859911
AllCCS[M+HCOO]-259.29532859911
DeepCCS[M+H]+187.7230932474
DeepCCS[M-H]-185.83530932474
DeepCCS[M-2H]-220.50130932474
DeepCCS[M+Na]+195.21530932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 10V, Positive-QTOFsplash10-000i-1931000110-da1db28a855c878b4aed2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 20V, Positive-QTOFsplash10-000j-1921000000-5675ad3c288d421286972015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 40V, Positive-QTOFsplash10-00ks-2910000000-64ab778c97047046a2d92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 10V, Negative-QTOFsplash10-017i-7930142460-c2298a969e995ad3d00a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 20V, Negative-QTOFsplash10-001i-5910100010-7599cb988facd52223da2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 40V, Negative-QTOFsplash10-057i-6900100000-f5f10442ccac27dc38eb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 10V, Negative-QTOFsplash10-000i-0000000090-073f428b3307881724332021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 20V, Negative-QTOFsplash10-014r-9200102230-8569a6d934e6ef3618382021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 40V, Negative-QTOFsplash10-0170-4003402900-aa858b6cf989ef7545e12021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 10V, Positive-QTOFsplash10-000i-0000000190-722be0a11d66c5eb058c2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 20V, Positive-QTOFsplash10-000i-0911001570-3a8be9989cbf457b70312021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - butanoyl-CoA 40V, Positive-QTOFsplash10-001i-0019000000-35adb55601f58e5ce0ac2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030704
KNApSAcK IDNot Available
Chemspider ID109043
KEGG Compound IDC00136
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15517
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available