ContaminantDB: 4,4''-bis(N-feruloyl)serotonin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:00:05 UTC

Update Date

2016-11-09 01:21:08 UTC

Accession Number

CHEM034545

Identification

Common Name

4,4''-bis(N-feruloyl)serotonin

Class

Small Molecule

Description

4,4''-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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4-Chlorophenyl)-sulfamoyl azide	HMDB
(P-Chlorophenyl)-sulfamoyl azide	HMDB
(P-Chlorophenyl)sulfamoyl azide	HMDB
4,4''-Bi[N-(4-hydroxy-3-methoxycinnamoyl)serotonin]	HMDB
4-Chlorophenylaminosulfonyl azide	HMDB
N-(P-Chlorophenyl)sulfamoyl azide	HMDB
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-enimidate	Generator

Chemical Formula

C₄₀H₃₈N₄O₈

Average Molecular Mass

702.752 g/mol

Monoisotopic Mass

702.269 g/mol

CAS Registry Number

175702-03-1

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

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 Key

URHRFQQPWDNDQE-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

N-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	4.96	ALOGPS
logP	5.47	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	1.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.16 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	200.39 m³·mol⁻¹	ChemAxon
Polarizability	72.54 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054k-2940210000-9de4e845346cab44178b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufr-0601051900-a0aac18dd7f049b3a8c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0906341100-6f7cacc8308fc022a9a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-0908101000-bc3c141c5a72711a23d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0100000900-9d3b8e87a3c81f66d6ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-0903243400-7530d5bb4961682c9193	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-2901011000-d0f391a697189b28f6eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000002900-037ce48832b1486c1ffa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0541-0500209000-2a63700d866aeccac25f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kc2-0200019000-f15c27e3826012e2cafe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0100022900-447444d39ecae1822249	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h90-0510059300-64225bc303603f36766f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0903023000-a30fdb0c334d8e30e9ba	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041433

FooDB ID

FDB021384

Phenol Explorer ID

Not Available

KNApSAcK ID

C00055553

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

8660299

ChEBI ID

Not Available

PubChem Compound ID

10484893

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

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.

4,4''-bis(N-feruloyl)serotonin (CHEM034545)

Structure for CHEM034545: 4,4''-bis(N-feruloyl)serotonin