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Identification
YMDB IDYMDB00496
Name4-hydroxybenzoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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
Thumb
Synonyms
  • 4-Hydroxybenzoyl-CoA
  • 4-Hydroxybenzoyl-coenzyme A
  • Coenzyme A, S-(4-hydroxybenzoate)
  • p-hydroxybenzoyl-CoA
  • p-hydroxybenzoyl-coenzyme A
  • S-(4-hydroxybenzoyl)-CoA
  • coenzyme A, S-(4-Hydroxybenzoic acid)
CAS number27718-41-8
WeightAverage: 887.64
Monoisotopic: 887.136337737
InChI KeyLTVXPVBFJBTNIJ-TYHXJLICSA-N
InChIInChI=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
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 IUPAC Name4-hydroxybenzoyl coenzyme A
Chemical FormulaC28H40N7O18P3S
SMILESCC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C1=CC=C(O)C=C1
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.28 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • lipid particle
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG Reactions
water + 4-hydroxybenzoyl-CoA4-Hydroxybenzoic acid + hydron + Coenzyme A
NAD + water + 4-Coumaroyl-CoA + Coenzyme ANADH + Acetyl-CoA + hydron + 4-hydroxybenzoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-0931000110-997001eb3c6779e12ce0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0911000000-1200c35c00ca3f1ba304JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-1910000000-75c48e5aa6dd0bd48474JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-3900021430-36523ae155149e41ceecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2901010010-343f3827cb88f1034fbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-7dd93b016d26e0cb0ccfJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15500
HMDB IDHMDB06467
Pubchem Compound ID439862
Kegg IDC02949
ChemSpider ID24785373
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-201