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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:57:50 UTC
Update Date2022-03-07 03:17:39 UTC
HMDB IDHMDB0060140
Secondary Accession Numbers
  • HMDB60140
Metabolite Identification
Common Name4-Hydroxybenoyl-CoA
Description4-Hydroxybenoyl-CoA 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. 4-Hydroxybenoyl-CoA is a strong basic compound (based on its pKa).
Structure
Data?1563866020
Synonyms
ValueSource
4-Hydroxybenzoyl-coenzyme AChEBI
coenzyme A, S-(4-Hydroxybenzoate)ChEBI
p-Hydroxybenzoyl-CoAChEBI
p-Hydroxybenzoyl-coenzyme AChEBI
S-(4-Hydroxybenzoyl)-CoAChEBI
coenzyme A, S-(4-Hydroxybenzoic acid)Generator
Chemical FormulaC28H40N7O18P3S
Average Molecular Weight887.64
Monoisotopic Molecular Weight887.136337737
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-[(2-{[2-(4-hydroxybenzoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name4-hydroxybenzoyl coenzyme A
CAS Registry NumberNot Available
SMILES
CC(C)(CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C28H40N7O18P3S/c1-28(2,22(39)25(40)31-8-7-18(37)30-9-10-57-27(41)15-3-5-16(36)6-4-15)12-50-56(47,48)53-55(45,46)49-11-17-21(52-54(42,43)44)20(38)26(51-17)35-14-34-19-23(29)32-13-33-24(19)35/h3-6,13-14,17,20-22,26,36,38-39H,7-12H2,1-2H3,(H,30,37)(H,31,40)(H,45,46)(H,47,48)(H2,29,32,33)(H2,42,43,44)/t17-,20-,21-,22+,26-/m1/s1
InChI KeyLTVXPVBFJBTNIJ-TYHXJLICSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Benzoic acid or derivatives
  • Purine
  • Thiobenzoic acid or derivatives
  • Imidazopyrimidine
  • Benzoyl
  • Monoalkyl phosphate
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Primary amine
  • Organosulfur compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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
Water Solubility5.68 g/LALOGPS
logP0.01ALOGPS
logP-5.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity194.86 m³·mol⁻¹ChemAxon
Polarizability79.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-291.48630932474
DeepCCS[M+Na]+265.50530932474
AllCCS[M+H]+260.132859911
AllCCS[M+H-H2O]+260.532859911
AllCCS[M+NH4]+259.632859911
AllCCS[M+Na]+259.532859911
AllCCS[M-H]-253.232859911
AllCCS[M+Na-2H]-257.532859911
AllCCS[M+HCOO]-262.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 10V, Positive-QTOFsplash10-00ks-0931000110-997001eb3c6779e12ce02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 20V, Positive-QTOFsplash10-000j-0911000000-1200c35c00ca3f1ba3042016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 40V, Positive-QTOFsplash10-000j-1910000000-75c48e5aa6dd0bd484742016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 10V, Negative-QTOFsplash10-0159-3900021430-36523ae155149e41ceec2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 20V, Negative-QTOFsplash10-001i-2901010010-343f3827cb88f1034fbf2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 40V, Negative-QTOFsplash10-057i-6900100000-7dd93b016d26e0cb0ccf2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 10V, Positive-QTOFsplash10-000i-0000000090-8935721e0e2c8c55b4af2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 20V, Positive-QTOFsplash10-0080-0514300290-2381c3a5a4bafa974cfd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 40V, Positive-QTOFsplash10-001i-0109000000-b2b6bd41459e8de8f2bf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 10V, Negative-QTOFsplash10-000i-0000000090-f05d48d535cf4c0cc4a42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 20V, Negative-QTOFsplash10-014r-5200000290-ba97d0b0075baa321a8f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxybenoyl-CoA 40V, Negative-QTOFsplash10-002r-9102310720-50cfce27a30eac259db52021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDDB01652
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02949
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound168718
PDB IDBCA
ChEBI ID15500
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 References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.