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

Details

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

SHOW SMILES / InChI
Structure of ALANINE

SMILES

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

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

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: 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
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
Structure and function of branched chain aminotransferases.
2001
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
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
Enantioseparation of chiral amino acids as the N(O,S)-ethoxycarbonylated diastereomeric esters by achiral dual-capillary column gas chromatography.
2001 Dec
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
Changes in the kinetic parameters of hepatic gamma-glutamyltransferase from streptozotocin-induced diabetic rats.
2001 Feb 9
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
Strong hydrogen-bonded amino acid dimers in L-alanine alaninium nitrate.
2001 Jul
Safinamide (Newron Pharmaceuticals).
2001 Jun
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
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue.
2001 Mar
Electrogenic Na(+)-dependent L-alanine transport in the lizard duodenum. Involvement of systems A and ASC.
2001 Mar
Characterization of the alanine racemases from two mycobacteria.
2001 Mar 15
Comparative functional study of clonal insulin-secreting cells cultured in five commercially available tissue culture media.
2001 Mar-Apr
Scaled quantum mechanical force field for alanyl-alanine peptide in solution.
2001 May
Molecular design and synthesis of artificial ion channels based on cyclic peptides containing unnatural amino acids.
2001 May 4
Effect of a meal feeding schedule on hepatic glycogen synthesis and gluconeogenesis in rats.
2001 May-Jun
pH and kinetic isotope effects in d-amino acid oxidase catalysis.
2001 Nov
Spider silk fibre extrusion: combined wide- and small-angle X-ray microdiffraction experiments.
2001 Oct 22
Degradation signals in ErbB-2 dictate proteasomal processing and immunogenicity and resist protection by cis glycine-alanine repeat.
2001 Sep 15
Possible involvement of amino acid transporters on S-nitroso-cysteine-induced inhibition of arachidonic acid release in PC12 cells.
2001 Sep 28
Targeting of EBNA1 for rapid intracellular degradation overrides the inhibitory effects of the Gly-Ala repeat domain and restores CD8+ T cell recognition.
2001 Sep 7
Physiological roles of free D- and L-alanine in the crayfish Procambarus clarkii with special reference to osmotic and anoxic stress responses.
2002 Apr
Dye-linked D-proline dehydrogenase from hyperthermophilic archaeon Pyrobaculum islandicum is a novel FAD-dependent amino acid dehydrogenase.
2002 Apr 12
Antitumour and toxic effects on Wistar rats of two new platinum complexes.
2002 Feb
Glycine and alanine dehydrogenase activities are catalyzed by the same protein in Mycobacterium smegmatis: upregulation of both activities under microaerophilic adaptation.
2002 Jan
Formation of D-alanyl-lipoteichoic acid is required for adhesion and virulence of Listeria monocytogenes.
2002 Jan
Highly selective molecularly imprinted overoxidized polypyrrole colloids: one-step preparation technique.
2002 Jan
The unique ribbon morphology of the major ampullate silk of spiders from the genus Loxosceles (recluse spiders).
2002 Jan-Feb
Nepenthes insignis uses a C2-portion of the carbon skeleton of L-alanine acquired via its carnivorous organs, to build up the allelochemical plumbagin.
2002 Mar
A Y2 receptor mimetic aptamer directed against neuropeptide Y.
2002 Mar 29
Mechanisms of the protective effect of L-alanine to D-galactosamine-induced hepatocellular injury: comparative studies of L-alanine and pyruvate.
2002 Mar 8
Structural characterization of the M* partly folded intermediate of wild type and P138A aspartate aminotransferase from Escherichia coli.
2002 May 17
Reaction mechanism of alanine racemase from Bacillus stearothermophilus: x-ray crystallographic studies of the enzyme bound with N-(5'-phosphopyridoxyl)alanine.
2002 May 24
3-Hydroxykynurenine transaminase identity with alanine glyoxylate transaminase. A probable detoxification protein in Aedes aegypti.
2002 May 3
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:58 UTC 2023
Edited
by admin
on Fri Dec 15 15:15:58 UTC 2023
Record UNII
OF5P57N2ZX
Record Status Validated (UNII)
Record Version
  • Download
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 IMPURITY]
Common Name English
SERINE IMPURITY A [EP IMPURITY]
Common Name English
ALANINE [MI]
Common Name English
VALINE IMPURITY A [EP IMPURITY]
Common Name English
ALANINE [VANDF]
Common Name English
ALANINE [USAN]
Common Name English
ALANINE [USP MONOGRAPH]
Common Name English
NSC-206315
Code English
L-ALANINE [USP-RS]
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
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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LOINC 32222-2
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LOINC 22657-1
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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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LOINC 25301-3
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CFR 21 CFR 172.320
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LOINC 25843-4
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CFR 21 CFR 310.532
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LOINC 57994-6
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LOINC 13704-2
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NDF-RT N0000175780
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LOINC 1735-0
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LOINC 16323-8
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LOINC 56671-1
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LOINC 53150-9
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LOINC 26795-5
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DSLD 2407 (Number of products:622)
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LOINC 15137-3
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LOINC 50167-6
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LOINC 1738-4
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LOINC 22698-5
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LOINC 20636-7
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Code System Code Type Description
DAILYMED
OF5P57N2ZX
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
PRIMARY
MERCK INDEX
m1467
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PRIMARY Merck Index
CHEBI
16449
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
PRIMARY
FDA UNII
OF5P57N2ZX
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
PRIMARY
RS_ITEM_NUM
1012509
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
PRIMARY
HSDB
1801
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-273-8
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PRIMARY
CAS
56-41-7
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PRIMARY
SMS_ID
100000092328
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PRIMARY
DRUG BANK
DB00160
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
PRIMARY
MESH
D000409
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PRIMARY
CHEBI
57972
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PRIMARY
NCI_THESAURUS
C29605
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PRIMARY
DRUG CENTRAL
4255
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PRIMARY
CHEBI
16977
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PRIMARY
ChEMBL
CHEMBL12198
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PRIMARY
EPA CompTox
DTXSID20873899
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PRIMARY
CHEBI
46217
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PRIMARY
WIKIPEDIA
ALANINE
Created by admin on Fri Dec 15 15:15:58 UTC 2023 , Edited by admin on Fri Dec 15 15:15:58 UTC 2023
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
NSC
206315
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PRIMARY
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