N-ACETYL-L-TRYPTOPHAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H14N2O3
Molecular Weight	246.2619
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI

InChIKey=DZTHIGRZJZPRDV-LBPRGKRZSA-N

InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H14N2O3
Molecular Weight	246.2619
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13233223 | https://www.ncbi.nlm.nih.gov/pubmed/25986728 | https://www.ncbi.nlm.nih.gov/pubmed/22485158 | https://www.ncbi.nlm.nih.gov/pubmed/21466790

Acetyltryptophan, L- functions readily as a component of the food in place of the free amino acid. Acetyltryptophan, L- is a neurokinin-1 receptor antagonist. It significantly improved motor and cognitive outcomes in models of Parkinson’s diseases, as well as reduced brain edema and axonal injury in experimental traumatic brain injury and stroke. It is a potent therapeutic agent for the treatment of amyotrophic lateral sclerosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neurokinin 1 receptor 35 Target ID: CHEMBL249 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26031348	Antagonist 2778
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26031348	Inhibitor 8297
Alpha-chymotrypsin 2 Target ID: CHEMBL3314 Sources: https://www.ncbi.nlm.nih.gov/pubmed/518837	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Amyotrophic lateral sclerosis 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25986728 https://www.ncbi.nlm.nih.gov/pubmed/26031348	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22485158 https://www.ncbi.nlm.nih.gov/pubmed/24637127	Primary	Preclinical	Unknown Approved Use Unknown
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21466790	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Treatment with a substance P receptor antagonist is neuroprotective in the intrastriatal 6-hydroxydopamine model of early Parkinson's disease.	2012	22485158
N-acetyl-L-tryptophan delays disease onset and extends survival in an amyotrophic lateral sclerosis transgenic mouse model.	2015 Aug	25986728
N-acetyl-l-tryptophan, but not N-acetyl-d-tryptophan, rescues neuronal cell death in models of amyotrophic lateral sclerosis.	2015 Sep	26031348

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 2 uL of 50 nM

Route of Administration: Other

In Vitro Use Guide

Incubation with Acetyltryptophan,L- resulted in statistically significant inhibition of H2O2-mediated NSC-34 motoneuron cell death. The resulting curve (plotted semi-logarithmically) define the IC50 and maximum protection afforded by acetyltryptophan, L- (0.3 uM and 47%, respectively).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:46:12 GMT 2023` Edited by `admin` on `Fri Dec 15 18:46:12 GMT 2023`
Record UNII	U9264T8OAE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N-ACETYL-L-TRYPTOPHAN

Systematic Name

English

N-ACETYL-L-TRYPTOPHANATE

Systematic Name

English

L-TRYPTOPHAN, N-ACETYL-

Systematic Name

English

TRYPTOPHAN RELATED COMPOUND B [USP-RS]

Common Name

English

NSC-90726

Code

English

L-ACETYLTRYPTOPHAN

Common Name

English

(S)-N-ACETYLTRYPTOPHAN

Systematic Name

English

TRYPTOPHAN RELATED COMPOUND B

Common Name

English

TRYPTOPHAN, N-ACETYL-, L-

Systematic Name

English

ACETYL-L-TRYPTOPHAN

Systematic Name

English

ACETYLTRYPTOPHAN, L-

Common Name

English

ACETYLTRYPTOPHANATE

Common Name

English

Code System Code Type Description

NSC

90726