Record Information
Version1.0
Creation date2010-04-08 22:15:40 UTC
Update date2019-11-26 03:20:18 UTC
Primary IDFDB021384
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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. Based on a literature review very few articles have been published on 4,4''-bis(N-feruloyl)serotonin.
CAS Number175702-03-1
Structure
Thumb
Synonyms
SynonymSource
(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
(p-chlorophenyl)sulfamoyl azidebiospider
4,4''-Bis(N-feruloyl)serotonindb_source
N-(p-chlorophenyl)sulfamoyl azidebiospider
Sulfamoyl azide, (4-chlorophenyl)-biospider
Sulfamoyl azide, (4-chlorophenyl)- (9CI)biospider
Sulfamoyl azide, (p-chlorophenyl)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP4.96ALOGPS
logP5.47ChemAxon
logS-5.8ALOGPS
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
Chemical FormulaC40H38N4O8
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=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
Average Molecular Weight702.7517
Monoisotopic Molecular Weight702.268964212
Classification
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

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.36%; H 5.45%; N 7.97%; O 18.21%DFC
Melting PointMp 158-160°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data317 (e 38800) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-054k-2940210000-9de4e845346cab44178bSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4''-bis(N-feruloyl)serotonin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0601051900-a0aac18dd7f049b3a8c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0906341100-6f7cacc8308fc022a9a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-0908101000-bc3c141c5a72711a23d7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100000900-9d3b8e87a3c81f66d6abSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0903243400-7530d5bb4961682c9193Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2901011000-d0f391a697189b28f6ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000002900-037ce48832b1486c1ffaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0541-0500209000-2a63700d866aeccac25fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kc2-0200019000-f15c27e3826012e2cafeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0100022900-447444d39ecae1822249Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-0510059300-64225bc303603f36766fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0903023000-a30fdb0c334d8e30e9baSpectrum
NMRNot Available
ChemSpider ID8660299
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10484893
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41433
CRC / DFC (Dictionary of Food Compounds) IDNSC90-R:NSC93-U
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference