U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C3H7NO2
Molecular Weight 89.0933
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALANINE

SMILES

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

InChI

InChIKey=QNAYBMKLOCPYGJ-REOHCLBHSA-N
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

HIDE SMILES / InChI

Description
Sources: Nelson, David L.; Cox, Michael M. (2005), Principles of Biochemistry (4th ed.), New York: W. H. Freeman.
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00160

Alanine is a non-essential aminoacid encoded by GCU, GCC, GCA, and GCG codons. Besides being a building block of proteins, alanine plays a key role in glucose-alanine cycle. Alanine is medically used as a dietary supplement for conditions such as fructose intolerance, muscle atrophy, low birth weight.

Originator

Curator's Comment:: Alanine was first synthesized in 1850 by Adolph Strecker

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FREAMINE III 10%

Approved Use

Parenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal absorption of protein is impaired; or (3) protein requirements are substantially increased as with extensive burns. Dosage, route of administration, and concomitant infusion of non-protein calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance

Launch Date

5.4431998E10
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
2000 Apr 25
Primary structure, genomic organization, and functional and electrogenic characteristics of human system N 1, a Na+- and H+-coupled glutamine transporter.
2000 Aug 4
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.
2000 Jul 31
Water-soluble L-alanine and related oligopeptide conjugates with poly[(R,S)-3-hydroxybutanoic acid] oligomers, synthesis and structural studies by means of electrospray ionization multistage mass spectrometry.
2001
Functional examination of microencapsulated bioengineered insulin-secreting beta-cells.
2001
The structure of human mitochondrial branched-chain aminotransferase.
2001 Apr
Structure of Bombyx mori silk fibroin before spinning in solid state studied with wide angle x-ray scattering and (13)C cross-polarization/magic angle spinning NMR.
2001 Apr 15
Comparison of the omega-transaminases from different microorganisms and application to production of chiral amines.
2001 Aug
Analysis of the role of bacterial endospore cortex structure in resistance properties and demonstration of its conservation amongst species.
2001 Aug
Inhibition of Kupffer cells reduced CXC chemokine production and liver injury.
2001 Aug
Antifungal alkyl amino alcohols from the tropical marine sponge Haliclona n. sp.
2001 Dec
Effect of amino acids on goat cauda epididymal sperm cryopreservation using a chemically defined model system.
2001 Feb
Inhibitory effect of glycation on catalytic activity of alanine aminotransferase.
2001 Feb
5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line.
2001 Feb
(13)C chemical shift and (13)C-(14)N dipolar coupling tensors determined by (13)C rotary resonance solid-state NMR.
2001 Feb
Rapid kinetic and isotopic studies on dialkylglycine decarboxylase.
2001 Feb 6
Evidence for the transport of neutral as well as cationic amino acids by ATA3, a novel and liver-specific subtype of amino acid transport system A.
2001 Feb 9
Changes in the kinetic parameters of hepatic gamma-glutamyltransferase from streptozotocin-induced diabetic rats.
2001 Feb 9
[Activity of aminopeptidase and inter-alpha-trypsin inhibitor in serum of women in physiological labor].
2001 Jan
Purification and some properties of alanine racemase from a bivalve mollusc Corbicula japonica.
2001 Jan 1
Structure-activity relationships of neurokinin A (4-10) at the human tachykinin NK(2) receptor: the role of natural residues and their chirality.
2001 Jan 1
Inherited prion disease with A117V mutation of the prion protein gene: a novel Hungarian family.
2001 Jun
Dipolar and J encoded DQ MAS spectra under rotational resonance.
2001 Jun
Synthesis of homochiral tris(2-alkyl-2-aminoethyl)amine derivatives from chiral alpha-amino aldehydes and their application in the synthesis of water soluble chelators.
2001 Jun 18
Inhibitors of the bacterial cell wall biosynthesis enzyme MurC.
2001 Jun 4
Stimulation of protein biosynthesis in rat hepatocytes by extracts of Momordica charantia.
2001 Mar
Factors involved in the (near) anoxic survival time of Cerastoderma edule: associated bacteria vs. endogenous fuel.
2001 Mar
Structure, function, and tissue expression pattern of human SN2, a subtype of the amino acid transport system N.
2001 Mar
Electrogenic Na(+)-dependent L-alanine transport in the lizard duodenum. Involvement of systems A and ASC.
2001 Mar
Oxygen K-edge X-ray absorption near edge structures (XANES) of sublimated films of amino acids.
2001 Mar 1
Platinum(IV) complexes with dipeptide. X-ray crystal structure, 195Pt NMR spectra, and their inhibitory glucose metabolism activity in Candida albicans.
2001 Mar 26
A model for enzyme-substrate interaction in alanine racemase.
2001 Mar 28
Comparative functional study of clonal insulin-secreting cells cultured in five commercially available tissue culture media.
2001 Mar-Apr
Reduction of large neutral amino acid levels in plasma and brain of hyperleucinemic rats.
2001 May
Effect of a meal feeding schedule on hepatic glycogen synthesis and gluconeogenesis in rats.
2001 May-Jun
Comparison of vaginal aminopeptidase enzymatic activities in various animals and in humans.
2001 Nov
Evidence for altered hepatic gluconeogenesis in patients with cirrhosis using in vivo 31-phosphorus magnetic resonance spectroscopy.
2001 Oct
Biochemical characterization of a phosphinate inhibitor of Escherichia coli MurC.
2001 Oct 9
Possible involvement of amino acid transporters on S-nitroso-cysteine-induced inhibition of arachidonic acid release in PC12 cells.
2001 Sep 28
Antitumour and toxic effects on Wistar rats of two new platinum complexes.
2002 Feb
Preparation of optically active allothreonine via optical resolution by replacing crystallization.
2002 Feb
Transport of D-serine via the amino acid transporter ATB(0,+) expressed in the colon.
2002 Feb 22
Formation of D-alanyl-lipoteichoic acid is required for adhesion and virulence of Listeria monocytogenes.
2002 Jan
Oligomeric beta(beta)(alpha) miniprotein motifs: pivotal role of single hinge residue in determining the oligomeric state.
2002 Jan 23
Patents

Sample Use Guides

Alanine is a nutrient, available from animal and vegetarian sources. It could be administered intravenously.
Route of Administration: Other
In Vitro Use Guide
The extent of transamination was measured by measuring the pyruvate concentration after 10 minutes incubation period with the alanine aminotransferase. The Michaelis constant for alanine was shown to be 28 mM for alanine.
Name Type Language
ALANINE
EP   HSDB   II   INCI   INN   MI   USAN   USP   VANDF   WHO-DD  
USAN   INCI   INN  
Official Name English
ALANINE [INCI]
Common Name English
LYSINE ACETATE IMPURITY C [EP]
Common Name English
ALANINE [MI]
Common Name English
ALANINE [VANDF]
Common Name English
ALANINE [USAN]
Common Name English
ALANINE [USP]
Common Name English
NSC-206315
Code English
L-ALANINE [USP-RS]
Common Name English
VALINE IMPURITY A [EP]
Common Name English
ALANINE [WHO-DD]
Common Name English
ALANINE [INN]
Common Name English
(2S)-2-AMINOPROPANOIC ACID
Common Name English
ALANINE [HSDB]
Common Name English
L-ALANINE
FCC   JAN   USP-RS  
Systematic Name English
ALANINE [EP MONOGRAPH]
Common Name English
ALANINE [II]
Common Name English
L-ALANINE [JAN]
Common Name English
ALANINE, L-
Systematic Name English
SERINE IMPURITY A [EP]
Common Name English
L-ALANINE [FCC]
Common Name English
L-2-AMINOPROPANOIC ACID
Common Name English
Classification Tree Code System Code
LOINC 88018-7
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DSLD 256 (Number of products:46)
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LOINC 44291-3
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FDA ORPHAN DRUG 342911
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LOINC 47555-8
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CFR 21 CFR 172.320
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CFR 21 CFR 310.532
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NDF-RT N0000175780
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LOINC 1735-0
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DSLD 2407 (Number of products:622)
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LOINC 15137-3
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Code System Code Type Description
MERCK INDEX
M1467
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY Merck Index
FDA UNII
OF5P57N2ZX
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
HSDB
1801
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-273-8
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
CAS
56-41-7
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
USP_CATALOG
1012509
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00160
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
MESH
D000409
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
NCI_THESAURUS
C29605
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PRIMARY
DRUG CENTRAL
4255
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PRIMARY
ChEMBL
CHEMBL12198
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
WIKIPEDIA
ALANINE
Created by admin on Fri Jun 25 21:17:25 UTC 2021 , Edited by admin on Fri Jun 25 21:17:25 UTC 2021
PRIMARY
PUBCHEM
5950
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PRIMARY
INN
6161
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PRIMARY
EVMPD
SUB41388
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PRIMARY
EVMPD
SUB05290MIG
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PRIMARY
RXCUI
426
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PRIMARY RxNorm