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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:58:51 UTC
Update Date2022-03-07 03:17:39 UTC
HMDB IDHMDB0060153
Secondary Accession Numbers
  • HMDB60153
Metabolite Identification
Common Name4-Coumaroyl-CoA
Description4-Coumaroyl-CoA, also known as p-coumaroyl-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 a significant number of articles have been published on 4-Coumaroyl-CoA.
Structure
Data?1589391798
Synonyms
ValueSource
(e)-4-Coumaroyl-CoAChEBI
(e)-4-Coumaroyl-coenzyme AChEBI
trans-4-Coumaroyl-coenzyme AChEBI
4-Hydroxycinnamoyl-CoAKegg
trans-4-Coumaroyl-CoAKegg
4-Coumaroyl-coenzyme AHMDB
(e)-p-Coumaroyl-CoAHMDB
(e)-p-Coumaroyl-coenzyme AHMDB
4-Coumaroylcoenzyme AHMDB
p-Coumaroyl-CoAHMDB
p-Coumaroyl-coenzyme AHMDB
p-Coumaroylcoenzyme AHMDB
4-Coumaroyl-CoAMeSH, KEGG
Chemical FormulaC30H42N7O18P3S
Average Molecular Weight913.68
Monoisotopic Molecular Weight913.151989708
IUPAC Name4-({[({[(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)-2-hydroxy-N-{2-[(2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
Traditional Name4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-{2-[(2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid
CAS Registry Number119785-99-8
SMILES
CC(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=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=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
InChI KeyDMZOKBALNZWDKI-MATMFAIHSA-N
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
Ontology
Not AvailableNot 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 Solubility5.11 g/LALOGPS
logP0.16ALOGPS
logP-2ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area390.84 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity205.65 m³·mol⁻¹ChemAxon
Polarizability83.09 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+H]+275.2330932474
DeepCCS[M-H]-273.50630932474
DeepCCS[M-2H]-307.54230932474
DeepCCS[M+Na]+281.56130932474
AllCCS[M+H]+265.832859911
AllCCS[M+H-H2O]+266.232859911
AllCCS[M+NH4]+265.332859911
AllCCS[M+Na]+265.132859911
AllCCS[M-H]-262.432859911
AllCCS[M+Na-2H]-267.132859911
AllCCS[M+HCOO]-272.232859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 10V, Positive-QTOFsplash10-000i-1980000210-7cc2da8ded37eefebc802019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 20V, Positive-QTOFsplash10-0079-1980200000-640eb1c8c808f1d935f72019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 40V, Positive-QTOFsplash10-000i-1940000000-aa67eee5fe13e10550f52019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 10V, Negative-QTOFsplash10-01pk-2910031322-e82af6bab5c12560cef02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 20V, Negative-QTOFsplash10-001i-2901010000-d32151b09f0c4a5571f62019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 40V, Negative-QTOFsplash10-057i-4900100000-babcb42e11692c696d042019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 10V, Positive-QTOFsplash10-03di-0400000009-6f92bd67469e3969fe642021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 20V, Positive-QTOFsplash10-000i-0900200001-cb498b34cb06025c09252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 40V, Positive-QTOFsplash10-0a4i-0212900000-1b1996d9d74c393866902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 10V, Negative-QTOFsplash10-03di-0000000009-dc75f12cfe0d9e7420b22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 20V, Negative-QTOFsplash10-03xu-3700000595-78ad4ad607feb93405ca2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaroyl-CoA 40V, Negative-QTOFsplash10-0400-5512320290-3d4c8c1a4c6a3e2481432021-10-12Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00007280
Chemspider ID4944344
KEGG Compound IDC00223
BioCyc IDP-COUMAROYL-COA
BiGG IDNot Available
Wikipedia LinkCoumaroyl-CoA
METLIN IDNot Available
PubChem Compound6440013
PDB IDNot Available
ChEBI ID85531
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.