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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 of ABRINE

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

Molecular Formula C12H14N2O2
Molecular Weight 218.2518
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Sources: Justus Liebigs Annalen der Chemie (1934), 513, 1-25.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q8TF71
Gene ID: 117247.0
Gene Symbol: SLC16A10
Target Organism: Homo sapiens (Human)
3.1 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
N-methyltryptophan oxidase from Escherichia coli: reaction kinetics with N-methyl amino acid and carbinolamine substrates.
2001 Feb 6
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
pH and kinetic isotope effects on sarcosine oxidation by N-methyltryptophan oxidase.
2005 Mar 1
The X-ray structure of N-methyltryptophan oxidase reveals the structural determinants of substrate specificity.
2008 Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:05:45 GMT 2023
Edited
by admin
on Fri Dec 15 18:05:45 GMT 2023
Record UNII
P57TWL22IX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ABRINE
MI  
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
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40967027
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
CAS
526-31-8
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
PUBCHEM
160511
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
FDA UNII
P57TWL22IX
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-388-5
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
CHEBI
15334
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
CHEBI
72821
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY
MESH
C496492
Created by admin on Fri Dec 15 18:05:46 GMT 2023 , Edited by admin on Fri Dec 15 18:05:46 GMT 2023
PRIMARY