ALANINE, D-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C3H7NO2
Molecular Weight	89.0932
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](N)C(O)=O

InChI

InChIKey=QNAYBMKLOCPYGJ-UWTATZPHSA-N

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C3H7NO2
Molecular Weight	89.0932
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/16154544

D-alanine is an isomer of non-essential L-amino acid. D isomer is found in the cell walls of bacteria, but not in bacterial proteins. It was discovered, that being an endogenous agonist of the glycine site of the N-methyl-d-aspartate (NMDA) receptor, D-alanine can have beneficial effects on schizophrenia.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16154544	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16154544	Palliative		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification of a G protein-coupled receptor specifically responsive to beta-alanine.	2004 May 28	15037633
Cephalosporin-resistant pneumococci and sickle cell disease.	2005 Aug	16102306
D-Amino acid dipeptide production utilizing D-alanine-D-alanine ligases with novel substrate specificity.	2005 Jun	16233841
Conformational and quantitative characterization of oritavancin-peptidoglycan complexes in whole cells of Staphylococcus aureus by in vivo 13C and 15N labeling.	2006 Apr 7	16483598
Enzymatic characterization and crystal structure analysis of the D-alanine-D-alanine ligase from Helicobacter pylori.	2008 Sep	18320587
ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds.	2009 Feb 1	18321716
Comparative genomic analyses of nickel, cobalt and vitamin B12 utilization.	2009 Feb 10	19208259
Enterococcal surface protein Esp is not essential for cell adhesion and intestinal colonization of Enterococcus faecium in mice.	2009 Jan 29	19178704
Genome subtraction for novel target definition in Salmonella typhi.	2009 Oct 11	20198190
Crystal structure of the Apo form of D-Alanine:D-Alanine ligase (DDl) from Streptococcus mutans.	2010 Aug	20522004

Patents

Sample Use Guides

In Vivo Use Guide

100 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

It was studied the effect of D-alanine (10 mM), D-leucine (10 mM), D-methionine (10 mM), D-tryptophan (10 mM), and D-tyrosine (10 uM and 1 mM) on biofilm formation in two commonly studied laboratory strains of P. aeruginosa: PAO1 and PA14. In strains PAO1 and PA14, the addition of D-amino acids did not result in an inhibitory effect on biofilm growth in 24-well plates. Repeating the study in 96-well plates confirmed the findings that D-amino acids do not inhibit biofilm formation of P. aeruginosa. It was concluded that D-amino acids only slow the production of biofilms rather than completely prevent biofilm formation.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:17:38 GMT 2023` Edited by `admin` on `Sat Dec 16 02:17:38 GMT 2023`
Record UNII	E3UDS4613U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALANINE, D-

Systematic Name

English

ALANINE D-FORM [MI]

Common Name

English

(R)-ALANINE

Systematic Name

English

(R)-2-AMINOPROPANOIC ACID

Systematic Name

English

ALANINE D-FORM

Common Name

English

NSC-158286

Code

English

D-ALANINE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID3045649