ABRINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H14N2O2
Molecular Weight	218.2518
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

InChI

InChIKey=CZCIKBSVHDNIDH-NSHDSACASA-N

InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)/t11-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25527549
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19239732 | https://www.ncbi.nlm.nih.gov/pubmed/24522983

L-Abrine (N-Methyl-L-Tryptophan) is an indoleamino acid produced by Abrus precatoriu that shows radical scavenging and antioxidant properties in vitro. Abrin is a toxic protein produced by the ornamental plant Abrus precatorius, and it is of concern as a biothreat agent. The small coextracting molecule N-methyl-L-tryptophan (L-abrine) is specific to members of the genus Abrus and L-Abrine concentrations in A. precatorius seeds is greater than the abrin concentrations reported in seeds. L-Abrine is found only in plants of the genus Abrus, which are used medicinally but not as food. Therefore, the presence of L-abrine is a reliable and specific indicator for the presence of abrin in food products.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
SLC16A10 protein 1 Target ID: CHEMBL2073719 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11827462	Inhibitor 8297
Monocarboxylate transporter 10 1 Target ID: Q8TF71 Gene ID: 117247.0 Gene Symbol: SLC16A10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11278508	Inhibitor 8297		3.1 mM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Steroid hormone activity of flavonoids and related compounds.	2000 Jul	10989984
Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.	2001 Feb 6	11170472
Glycine oxidase from Bacillus subtilis. Characterization of a new flavoprotein.	2002 Mar 1	11744710
Tautomeric rearrangement of a dihydroflavin bound to monomeric sarcosine oxidase or N-methyltryptophan oxidase.	2003 Feb 4	12549903
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
pH and kinetic isotope effects on sarcosine oxidation by N-methyltryptophan oxidase.	2005 Mar 1	15723552
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Insights into the mechanism of flavoprotein-catalyzed amine oxidation from nitrogen isotope effects on the reaction of N-methyltryptophan oxidase.	2007 Jun 26	17542620
The X-ray structure of N-methyltryptophan oxidase reveals the structural determinants of substrate specificity.	2008 Jun	18186483
Kynurenine pathway metabolites in humans: disease and healthy States.	2009	22084578
Engineering galanin analogues that discriminate between GalR1 and GalR2 receptor subtypes and exhibit anticonvulsant activity following systemic delivery.	2010 Feb 25	20121116
Transcriptomic profile of host response in mouse brain after exposure to plant toxin abrin.	2012 Sep 4	22595364
The Fas/Fas ligand apoptotic pathway is involved in abrin-induced apoptosis.	2013 Sep	23788630

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

ABRINE

Systematic Name

English

(S)-3-(1H-INDOL-3-YL)-2-METHYLAMINOPROPIONIC ACID

Systematic Name

English

N-METHYL-L-TRYPTOPHAN

Systematic Name

English

ABRINE [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m1281