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4-Coumaroyl-CoA (YMDB00497)

Identification
YMDB IDYMDB00497
Name4-Coumaroyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCoumaroyl-CoA belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Based on a literature review very few articles have been published on Coumaroyl-CoA.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 4-Coumaroyl-CoA
  • 4-Coumaroyl-coenzyme A
  • 4-Hydroxycinnamoyl-CoA
  • p-Coumaroyl-CoA
CAS number119785-99-8
WeightAverage: 913.677
Monoisotopic: 913.151987801
InChI KeyDMZOKBALNZWDKI-MATMFAIHSA-N
InChIInChI=1S/C30H42N7O18P3S/c1-30(2,25(42)28(43)33-10-9-20(39)32-11-12-59-21(40)8-5-17-3-6-18(38)7-4-17)14-52-58(49,50)55-57(47,48)51-13-19-24(54-56(44,45)46)23(41)29(53-19)37-16-36-22-26(31)34-15-35-27(22)37/h3-8,15-16,19,23-25,29,38,41-42H,9-14H2,1-2H3,(H,32,39)(H,33,43)(H,47,48)(H,49,50)(H2,31,34,35)(H2,44,45,46)/b8-5+/t19-,23-,24-,25+,29-/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-{[3-(4-hydroxyphenyl)prop-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name4-coumaroyl-coa
Chemical FormulaC30H42N7O18P3S
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)C=CC1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2-enoyl 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
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Styrene
  • Monoalkyl phosphate
  • Aminopyrimidine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Alkyl phosphate
  • Monocyclic benzene moiety
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Carboxamide group
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Carbonyl group
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.11 g/LALOGPS
logP0.36ALOGPS
logP-3.6ChemAxon
logS-2.2ALOGPS
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
Refractivity204.61 m³·mol⁻¹ChemAxon
Polarizability83.59 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 Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
Phenylalanine metabolismec00360 Map00360
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG Reactions
NAD + water + 4-Coumaroyl-CoA + Coenzyme A → NADH + Acetyl-CoA + hydron + 4-hydroxybenzoyl-CoA
Adenosine triphosphate + trans-4-Coumaric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + 4-Coumaroyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1980000210-ae7585c3f7c5a3ace22aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0980100000-ee66e5a3178e65c99417JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2940000000-e5e685e6cba2b05a7068JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01rt-2910031322-cd497e088690b0636610JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2901110010-4a99bba1039a26ec11c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-6900100000-e0951a04906b8e49efc1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0230000029-955240ef572d9ba3624fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tb-0930614264-fd880163921c9fd1066bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0612900000-bd23ce85548b6b0a10ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000009-25f2b3cc402415b423d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vi-7910207446-7441bdfd6ebb32013db1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-5701513930-13808f7f5018e2618775JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
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 ID15499
HMDB IDHMDB0304822
Pubchem Compound ID6440013
Kegg IDC00223
ChemSpider ID24785406
FOODB IDFDB112405
WikipediaCoumaroyl-CoA
BioCyc IDP-COUMAROYL-COA