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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:07:13 UTC
Update Date2021-04-08 14:45:45 UTC
HMDB IDHMDB0041433
Secondary Accession Numbers
  • HMDB41433
Metabolite Identification
Common Name4,4''-bis(N-feruloyl)serotonin
Description4,4''-bis(N-feruloyl)serotonin belongs to the class of organic compounds known as n-acylserotonins. These are aromatic heterocyclic compounds containing a serotonin, in which the amine group is acylated. 4,4''-bis(N-feruloyl)serotonin is a moderately basic compound (based on its pKa). Outside of the human body, 4,4''-bis(N-feruloyl)serotonin has been detected, but not quantified in, fats and oils and herbs and spices. This could make 4,4''-bis(N-feruloyl)serotonin a potential biomarker for the consumption of these foods.
Structure
Data?1563863663
Synonyms
ValueSource
(4-Chlorophenyl)-sulfamoyl azideHMDB
(P-Chlorophenyl)-sulfamoyl azideHMDB
(P-Chlorophenyl)sulfamoyl azideHMDB
4,4''-Bi[N-(4-hydroxy-3-methoxycinnamoyl)serotonin]HMDB
4-Chlorophenylaminosulfonyl azideHMDB
N-(P-Chlorophenyl)sulfamoyl azideHMDB
Sulfamoyl azide, (4-chlorophenyl)- (9ci)HMDB
(2E)-N-{2-[5,5'-dihydroxy-3'-(2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}ethyl)-1H,1'H-[4,4'-biindole]-3-yl]ethyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidateGenerator
Chemical FormulaC40H38N4O8
Average Molecular Weight702.7517
Monoisotopic Molecular Weight702.268964212
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-{2-[5-hydroxy-4-(5-hydroxy-3-{2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]ethyl}-1H-indol-4-yl)-1H-indol-3-yl]ethyl}prop-2-enamide
Traditional Name(2E)-3-(4-hydroxy-3-methoxyphenyl)-N-{2-[5-hydroxy-4-(5-hydroxy-3-{2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]ethyl}-1H-indol-4-yl)-1H-indol-3-yl]ethyl}prop-2-enamide
CAS Registry Number175702-03-1
SMILES
COC1=C(O)C=CC(\C=C\C(=O)NCCC2=CNC3=C2C(=C(O)C=C3)C2=C(O)C=CC3=C2C(CCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CN3)=C1
InChI Identifier
InChI=1S/C40H38N4O8/c1-51-33-19-23(3-9-29(33)45)5-13-35(49)41-17-15-25-21-43-27-7-11-31(47)39(37(25)27)40-32(48)12-8-28-38(40)26(22-44-28)16-18-42-36(50)14-6-24-4-10-30(46)34(20-24)52-2/h3-14,19-22,43-48H,15-18H2,1-2H3,(H,41,49)(H,42,50)/b13-5+,14-6+
InChI KeyURHRFQQPWDNDQE-ACFHMISVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylserotonins. These are aromatic heterocyclic compounds containing a serotonin, in which the amine group is acylated.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentN-acylserotonins
Alternative Parents
Substituents
  • N-acylserotonin
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid amide
  • Methoxyphenol
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Anisole
  • Phenoxy compound
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point158 - 160 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP10(4.96) g/LALOGPS
logP10(5.47) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)8.68ChemAxon
pKa (Strongest Basic)1.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.16 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity200.39 m³·mol⁻¹ChemAxon
Polarizability72.54 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,4''-bis(N-feruloyl)serotoninCOC1=C(O)C=CC(\C=C\C(=O)NCCC2=CNC3=C2C(=C(O)C=C3)C2=C(O)C=CC3=C2C(CCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CN3)=C19149.5Standard polar33892256
4,4''-bis(N-feruloyl)serotoninCOC1=C(O)C=CC(\C=C\C(=O)NCCC2=CNC3=C2C(=C(O)C=C3)C2=C(O)C=CC3=C2C(CCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CN3)=C15498.4Standard non polar33892256
4,4''-bis(N-feruloyl)serotoninCOC1=C(O)C=CC(\C=C\C(=O)NCCC2=CNC3=C2C(=C(O)C=C3)C2=C(O)C=CC3=C2C(CCNC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CN3)=C17709.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-2940210000-9de4e845346cab44178b2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,4''-bis(N-feruloyl)serotonin GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 10V, Positive-QTOFsplash10-0ufr-0601051900-a0aac18dd7f049b3a8c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 20V, Positive-QTOFsplash10-002b-0906341100-6f7cacc8308fc022a9a02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 40V, Positive-QTOFsplash10-000t-0908101000-bc3c141c5a72711a23d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 10V, Negative-QTOFsplash10-0udi-0100000900-9d3b8e87a3c81f66d6ab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 20V, Negative-QTOFsplash10-0ufr-0903243400-7530d5bb4961682c91932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 40V, Negative-QTOFsplash10-0006-2901011000-d0f391a697189b28f6eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 10V, Negative-QTOFsplash10-0udi-0000002900-037ce48832b1486c1ffa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 20V, Negative-QTOFsplash10-0541-0500209000-2a63700d866aeccac25f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 40V, Negative-QTOFsplash10-0kc2-0200019000-f15c27e3826012e2cafe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 10V, Positive-QTOFsplash10-0udi-0100022900-447444d39ecae18222492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 20V, Positive-QTOFsplash10-0h90-0510059300-64225bc303603f36766f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,4''-bis(N-feruloyl)serotonin 40V, Positive-QTOFsplash10-03dr-0903023000-a30fdb0c334d8e30e9ba2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB021384
KNApSAcK IDC00055553
Chemspider ID8660299
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10484893
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .