N-ACETYL-DL-TRYPTOPHAN

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H14N2O3
Molecular Weight	246.2619
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC(CC1=CNC2=C1C=CC=C2)C(O)=O

InChI

InChIKey=DZTHIGRZJZPRDV-UHFFFAOYSA-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)

HIDE SMILES / InChI

Molecular Formula	C13H14N2O3
Molecular Weight	246.2619
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.jbc.org/content/160/1/31.short | https://www.ncbi.nlm.nih.gov/pubmed/27987726 | https://www.ncbi.nlm.nih.gov/pubmed/27748798

Acetyltryptophan,DL- functions readily as a component of the food in place of the free amino acid - a greater amount of acetyltryptophane,DL- than dl-tryptophane may be available to man. Acetyltryptophan,DL- is used as an additive in the protein microbubbles, used in various biomedical applications such as contrast imaging, targeted drug and gene delivery, delivery of drugs through blood brain barrier (BBB) and IV O2 delivery etc. In the breast cancer biomarkers search, lower levels of endogenous metabolite Acetyltryptophan, DL- was identified in the fluid from the affected breasts compared to the control breast fluid.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
release of cytochrome c from mitochondria 2 Target ID: GO:0001836 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18799679 \| https://www.ncbi.nlm.nih.gov/pubmed/26031348	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27748798	Diagnostic		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The amino acid requirements of man. VIII. The metabolic availability of the optical isomers of acetyltryptophan.	1955 Jan	13233223
Metabolomic profiling of breast tumors using ductal fluid.	2016 Dec	27748798
Effect of PEGylation on performance of protein microbubbles and its comparison with lipid microbubbles.	2017 Feb 1	27987726

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Incubation with Acetyltryptophan,DL- 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, DL- (1.0 uM and 22%, respectively).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:43:56 UTC 2023` Edited by `admin` on `Sat Dec 16 07:43:56 UTC 2023`
Record UNII	4460NBV53F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N-ACETYL-DL-TRYPTOPHAN

Systematic Name

English

NSC-49124

Code

English

DL-ACETYLTRYPTOPHAN

Common Name

English

N-ACETYLTRYPTOPHAN

Systematic Name

English

ACETYLTRYPTOPHAN, DL- [II]

Common Name

English

Acetyltryptophan [WHO-DD]

Common Name

English

ACETYLTRYPTOPHAN, DL-

Common Name

English

N-ACETYLTRYPTOPHAN [EP MONOGRAPH]

Common Name

English

ACETYLTRYPTOPHAN

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73539