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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 12:40:54 UTC
Update Date2021-09-24 12:40:54 UTC
HMDB IDHMDB0304822
Secondary Accession NumbersNone
Metabolite Identification
Common NameCoumaroyl-CoA
Description4-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. Thus, 4-coumaroyl-CoA is considered to be a fatty ester lipid molecule. 4-Coumaroyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
4-Coumaroyl-coenzyme AChEBI
4-Hydroxycinnamoyl-CoAChEBI
Chemical FormulaC30H42N7O18P3S
Average Molecular Weight913.677
Monoisotopic Molecular Weight913.151987801
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 Name4-coumaroyl-coa
CAS Registry NumberNot Available
SMILES
[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)C=CC1=CC=C(O)C=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
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)/t19-,23-,24-,25+,29-/m1/s1
InChI KeyDMZOKBALNZWDKI-FUEUKBNZSA-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
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
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
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]+266.07632859911
AllCCS[M+H-H2O]+266.55832859911
AllCCS[M+Na]+265.42732859911
AllCCS[M+NH4]+265.57932859911
AllCCS[M-H]-263.48232859911
AllCCS[M+Na-2H]-268.14532859911
AllCCS[M+HCOO]-273.28132859911
DeepCCS[M-2H]-253.28630932474
DeepCCS[M+Na]+227.99830932474

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 - Coumaroyl-CoA 10V, Positive-QTOFsplash10-000i-1980000210-ae7585c3f7c5a3ace22a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 20V, Positive-QTOFsplash10-0079-0980100000-ee66e5a3178e65c994172016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 40V, Positive-QTOFsplash10-000i-2940000000-e5e685e6cba2b05a70682016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 10V, Negative-QTOFsplash10-01rt-2910031322-cd497e088690b06366102016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 20V, Negative-QTOFsplash10-001i-2901110010-4a99bba1039a26ec11c22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 40V, Negative-QTOFsplash10-056r-6900100000-e0951a04906b8e49efc12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 10V, Positive-QTOFsplash10-03di-0230000029-955240ef572d9ba3624f2021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 20V, Positive-QTOFsplash10-06tb-0930614264-fd880163921c9fd1066b2021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 40V, Positive-QTOFsplash10-0a4i-0612900000-bd23ce85548b6b0a10dd2021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 10V, Negative-QTOFsplash10-03di-0000000009-25f2b3cc402415b423d52021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 20V, Negative-QTOFsplash10-02vi-7910207446-7441bdfd6ebb32013db12021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coumaroyl-CoA 40V, Negative-QTOFsplash10-016r-5701513930-13808f7f5018e26187752021-10-22Wishart 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 IDFDB112405
KNApSAcK IDC00007280
Chemspider ID21864784
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15499
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