3,4,5-Trimethoxycinnamoylglycine
3,4,5-Trimethoxycinnamoylglycine.png

3,4,5-Trimethoxycinnamoylglycine is a theoretical alkaloid metabolite of elemicin believed to be psychedelic in humans.

3,4,5-Trimethoxycinnamoylglycine is believed to be the glycine conjugate of 3,4,5-Trimethoxycinnamic acid or simply an adduct of 3,4,5-Trimethoxycinnamaldehyde and glycine.

The closely related 4-Methoxycinnamoylglycine is a proven alkaloid metabolite of methyl chavicol found in humans.

Proven alkaloid metabolite of methyl chavicol Theoretical alkaloid metabolite of elemicin
4-Methoxycinnamoylglycine 3,4,5-Trimethoxycinnamoylglycine
N-(4-methoxycinnamoyl)glycine.png 3,4,5-Trimethoxycinnamoylglycine.png

Theoretical Metabolism Sequence

3,4,5-Trimethoxycinnamoylglycine is believed to form when glycine condenses with the aldehyde 3,4,5-Trimethoxycinnamaldehyde, a metabolite of elemicin.

Elemicin 3'-hydroxyisoelemicin 3,4,5-Trimethoxycinnamaldehyde 3,4,5-Trimethoxycinnamoylglycine
Elemicin is ingested orally Elemicin is hydroxylated at the 3 position creating 3'-hydroxyisoelemicin 3'-hydroxyisoelemicin is oxidized to form 3,4,5-Trimethoxycinnamaldehyde 3,4,5-Trimethoxycinnamaldehyde condenses with glycine creating
an the alkaloid adduct 3,4,5-Trimethoxycinnamoylglycine
elemicin.png 3'-hydroxyisoelemicin.png 3,4,5-Trimethoxycinnamaldehyde.png 3,4,5-Trimethoxycinnamoylglycine.png

Chemical Properties

Synonyms: {[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]amino}acetic acid; 2-[3-(3,4,5-trimethoxyphenyl)prop-2-enoylamino]acetic acid
PubChem Compound ID: 54079352
Molecular Weight: 295.28788 [g/mol]
Molecular Formula: C14H17NO6
XLogP3-AA: 1.1
H-Bond Donor: 2
H-Bond Acceptor: 6
IUPAC Name: 2-[3-(3,4,5-trimethoxyphenyl)prop-2-enoylamino]acetic acid
InChI: InChI=1S/C14H17NO6/c1-19-10-6-9(7-11(20-2)14(10)21-3)4-5-12(16)15-8-13
(17)18/h4-7H,8H2,1-3H3,(H,15,16)(H,17,18)
InChIKey: MLYZHOFRXCSOGN-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)NCC(=O)O


Related Compounds

Mescaline, a psychedelic from peyote cactus
the phenethylamine form of 3,4,5-Trimethoxycinnamoylglycine
mescaline.png
(2E)-N-Methyl-3-(3,4,5-trimethoxyphenyl)acrylamide
the decarboxylated form of 3,4,5-Trimethoxycinnamoylglycine
(2E)-N-Methyl-3-(3,4,5-trimethoxyphenyl)acrylamide.png
3,4,5-Trimethoxycinnamoylalanine
the alanine adduct of 3,4,5-Trimethoxycinnamaldehyde
3,4,5-Trimethoxycinnamoylalanine.png
(2E)-N-Ethyl-3-(3,4,5-trimethoxyphenyl)acrylamide
the decarboxylated form of 3,4,5-Trimethoxycinnamoylalanine
(2E)-N-Ethyl-3-(3,4,5-trimethoxyphenyl)acrylamide.png
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License