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N-Trans-feruloyltramine

PubChem CID
5280537
Structure
N-Trans-feruloyltramine_small.png
N-Trans-feruloyltramine_3D_Structure.png
Molecular Formula
Synonyms
  • N-trans-Feruloyltyramine
  • 66648-43-9
  • Moupinamide
  • Feruloyltyramine
  • Alfrutamide
Molecular Weight
313.3 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
N-feruloyltyramine is a member of tyramines. It has a role as a metabolite.
Moupinamide has been reported in Aristolochia kankauensis, Peperomia leptostachya, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-Trans-feruloyltramine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

NPNNKDMSXVRADT-WEVVVXLNSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

COC1=C(C=CC(=C1)/C=C/C(=O)NCCC2=CC=C(C=C2)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H19NO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

65646-26-6

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • feruloyltyramine
  • feruloyltyramine, (E)-isomer
  • feruloyltyramine, (Z)-isomer
  • moupinamide
  • N-feruloyltyramine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
313.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
2.1
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
313.13140809 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
313.13140809 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
78.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
390
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

144.5 - 145 °C

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
Source of Spectrum
QA-46-609-11
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
QA-48-813-4
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 MS-MS

1 of 2
Spectra ID
Ionization Mode
negative
Top 5 Peaks

312.123077 100

148.050629 22.94

1146.782837 15.60

176.032288 8.15

190.057053 7.88

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Notes
instrument=Maxis II HD Q-TOF Bruker
2 of 2
Spectra ID
Ionization Mode
positive
Top 5 Peaks

177.056168 100

121.065544 68.22

145.02948 52.84

117.034393 34.11

103.055298 23.24

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Notes
instrument=Maxis II HD Q-TOF Bruker

4.2.3 LC-MS

1 of 6
View All
Authors
CASMI2013 organizers
Instrument
LCMS-ITTOF, Shimadzu
Instrument Type
LC-ESI-ITTOF
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
120%
Column Name
Agilent Poroshell 120 EC-C18 (2.1 x 75 mm)
Top 5 Peaks

314.1364 999

315.1383 219

336.1194 187

337.1166 29

316.1437 23

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License
CC BY-SA
2 of 6
View All
Authors
CASMI2013 organizers
Instrument
LCMS-ITTOF, Shimadzu
Instrument Type
LC-ESI-ITTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
120%
Column Name
Agilent Poroshell 120 EC-C18 (2.1 x 75 mm)
Precursor m/z
314.1398
Precursor Adduct
[M+H]+
Top 5 Peaks

177.0548 999

145.0283 242

178.0586 117

146.0327 17

117.0337 13

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License
CC BY-SA

4.2.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
336.1242104146575
Ionization Mode
positive
Retention Time
2.94
Top 5 Peaks

320.09354465814545 100

292.10107019948214 95.13

278.0863739623661 67.45

336.1299456043069 64.06

321.1036685667084 52.51

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2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
314.1377922608485
Ionization Mode
positive
Retention Time
2.81
Top 5 Peaks

121.06573943375535 100

145.02743454616817 87.93

117.03119438535434 59.03

177.05614575592227 58.67

89.03811934260885 36

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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

8.2 Biochemical Reactions

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P273, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

12.2 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 ChEMBL Target Tree

15.5 UN GHS Classification

15.6 EPA DSSTox Classification

15.7 LOTUS Tree

15.8 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  7. ChEBI
  8. LOTUS - the natural products occurrence database
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    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  9. ChEMBL
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    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  10. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  11. FooDB
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    https://foodb.ca/about
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  14. KNApSAcK Species-Metabolite Database
  15. Natural Product Activity and Species Source (NPASS)
  16. MassBank Europe
  17. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  18. Metabolomics Workbench
  19. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  20. SpectraBase
  21. Springer Nature
  22. Thieme Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
  23. Wikidata
  24. PubChem
  25. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  26. GHS Classification (UNECE)
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS