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Identification
YMDB IDYMDB00154
NameL-Alanine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAlanine (abbreviated as Ala or A) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is often classified as a nonpolar amino acid. Alanine can be biosynthesized from pyruvate and branched chain amino acids such as valine, leucine, and isoleucine. It is most commonly produced by reductive amination of pyruvate. Alanine is tightly coupled to metabolic pathways such as glycolysis, gluconeogenesis, and the citric acid cycle. It also arises together with lactate and generates glucose from protein degradation via the alanine cycle. Alanine's catabolic pathway involves a simple aminotransferase reaction that directly produces pyruvate. Generally pyruvate produced by this pathway will result in the formation of oxaloacetate, although when the energy charge of a cell is low the pyruvate will be oxidized to CO2 and H2O via the pyruvate dehydrogenase complex and the citric acid cycle. This makes alanine a glucogenic amino acid.
Structure
Thumb
Synonyms
  • (2S)-2-Aminopropanoate
  • (2S)-2-Aminopropanoic acid
  • (S)-(+)-Alanine
  • (S)-2-amino-Propanoate
  • (S)-2-amino-Propanoic acid
  • (S)-2-Aminopropanoate
  • (S)-2-Aminopropanoic acid
  • (S)-Alanine
  • 2-Aminopropanoate
  • 2-Aminopropanoic acid
  • 2-Aminopropionate
  • 2-Aminopropionic acid
  • 2-Ammoniopropanoate
  • 2-Ammoniopropanoic acid
  • a-Alanine
  • a-Aminopropionate
  • a-Aminopropionic acid
  • Ala
  • Alanine
  • alpha-Alanine
  • alpha-Aminopropanoate
  • alpha-Aminopropanoic acid
  • alpha-Aminopropionate
  • alpha-Aminopropionic acid
  • L-(+)-Alanine
  • L-2-Aminopropanoate
  • L-2-Aminopropanoic acid
  • L-2-Aminopropionate
  • L-2-Aminopropionic acid
  • L-a-Alanine
  • L-a-Aminopropionate
  • L-a-Aminopropionic acid
  • L-alpha-Alanine
  • L-alpha-Aminopropionate
  • L-alpha-Aminopropionic acid
  • A
  • L-Alanin
  • L-Α-alanine
  • Abufène
  • Alanine doms-adrian brand
  • Alanine, L-isomer
  • Doms-adrian brand OF alanine
  • Doms adrian brand OF alanine
  • L-Isomer alanine
  • Alanine, L isomer
  • L Alanine
CAS number56-41-7
WeightAverage: 89.0932
Monoisotopic: 89.047678473
InChI KeyQNAYBMKLOCPYGJ-REOHCLBHSA-N
InChIInChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
IUPAC Name(2S)-2-aminopropanoic acid
Traditional IUPAC NameL-alanine
Chemical FormulaC3H7NO2
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlanine and derivatives
Alternative Parents
Substituents
  • Alanine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point300 °C
Experimental Properties
PropertyValueReference
Water Solubility164 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-2.85 [SANGSTER (1994)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility447 g/LALOGPS
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m³·mol⁻¹ChemAxon
Polarizability8.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB000556
SMPDB Pathways
L-alanine metabolismPW002373 ThumbThumb?image type=greyscaleThumb?image type=simple
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
Selenocompound metabolismPW002472 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Cysteine and methionine metabolismec00270 Map00270
Phenylalanine metabolismec00360 Map00360
Selenocompound metabolismec00450 Map00450
Taurine and hypotaurine metabolismec00430 Map00430
SMPDB Reactions
L-AlanineD-Alanine
Pyruvic acid + L-Glutamic acidOxoglutaric acid + L-Alanine
L-Valine + Pyruvic acidL-Alanine + Alpha-Ketoisovaleric acid
L-Cysteine + an [L-cysteine desulfurase] L-cysteine persulfide → an [L-cysteine desulfurase] L-cysteine persulfide + L-Alanine
L-Alanine + Oxoglutaric acidPyruvic acid + L-Glutamic acid
KEGG Reactions
L-3-Hydroxykynurenine + water3-Hydroxyanthranilic acid + L-Alanine
pimeloyl-CoA + L-Alaninehydron + 8-Amino-7-oxononanoic acid + Carbon dioxide + Coenzyme A
Glyoxylic acid + L-AlaninePyruvic acid + Glycine
Adenosine triphosphate + L-Alanine + tRNA(Ala) → Adenosine monophosphate + Pyrophosphate + Ala-tRNA(Ala)
Glutathione + L-AlanineL-cysteinylglycine + L-gamma-Glutamyl-L-alanine
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
15426 ± 308 µM YPD mediaaerobicBaker's yeastPMID: 7654310
18995 ± 380 µM YPG mediaaerobicBaker's yeastPMID: 7654310
7253 ± 145 µM SD mediaaerobicBaker's yeastPMID: 7654310
13699 ± 274 µM SG mediaaerobicBaker's yeastPMID: 7654310
9325 ± 186 µM M (molasses)aerobicBaker's yeastPMID: 7654310
18995 ± 380 µM MA (molasses)aerobicBaker's yeastPMID: 7654310
6677 ± 134 µM MB (molasses)aerobicBaker's yeastPMID: 7654310
12778 ± 255 µM MAB (molasses)aerobicBaker's yeastPMID: 7654310
6407 ± 320 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
16220 ± 3082 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
10000 ± 0 µM Minimal medium supplemented with glucoseaerobic;resting cellsBaker's yeastPMID: 4578278
16000 ± 9000 µM Minimal medium supplemented with ammonium and glucoseaerobic;growing cellsBaker's yeastPMID: 4578278
Conversion Details Here
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1347 ± 0 µM hops, malted barleyanaerobicBaker's yeastAlcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
Spectra
References
References:
  • Martinez-Force, E., Benitez, T. (1995). "Effects of varying media, temperature, and growth rates on the intracellular concentrations of yeast amino acids." Biotechnol Prog 11:386-392.7654310
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
  • Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Chibata I; Kakimoto T; Kato J Enzymatic production of L-alanine by Pseudomonas dacunhae. Applied microbiology (1965), 13(5), 638-45.
External Links:
ResourceLink
CHEBI ID16977
HMDB IDHMDB00161
Pubchem Compound ID5950
Kegg IDC00041
ChemSpider ID5735
FOODB IDFDB000556
WikipediaAlanine
BioCyc IDL-ALPHA-ALANINE

Enzymes

General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L- tryptophan metabolite L-kynurenine to form kynurenic acid (KA)
Gene Name:
BNA3
Uniprot ID:
P47039
Molecular weight:
50081.89844
Reactions
L-kynurenine + 2-oxoglutarate → 4-(2-aminophenyl)-2,4-dioxobutanoate + L-glutamate.
General function:
Involved in metabolic process
Specific function:
Has alanine:glyoxylate aminotransferase activity
Gene Name:
AGX1
Uniprot ID:
P43567
Molecular weight:
41906.80078
Reactions
L-alanine + glyoxylate → pyruvate + glycine.
General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur from cysteine to produce alanine. It supplies the inorganic sulfur for iron- sulfur (Fe-S) clusters. Involved in both tRNA-processing and mitochondrial metabolism
Gene Name:
NFS1
Uniprot ID:
P25374
Molecular weight:
54466.5
Reactions
L-cysteine + [enzyme]-cysteine → L-alanine + [enzyme]-S-sulfanylcysteine.
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the attachment of alanine to tRNA(Ala) in a two-step reaction:alanine is first activated by ATP to form Ala- AMP and then transferred to the acceptor end of tRNA(Ala). Also edits incorrectly charged tRNA(Ala) via its editing domain
Gene Name:
ALA1
Uniprot ID:
P40825
Molecular weight:
107276.0
Reactions
ATP + L-alanine + tRNA(Ala) → AMP + diphosphate + L-alanyl-tRNA(Ala).
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3- hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3- hydroxyanthranilic acid (3-OHAA), respectively
Gene Name:
BNA5
Uniprot ID:
Q05979
Molecular weight:
51031.60156
Reactions
L-kynurenine + H(2)O → anthranilate + L-alanine.
L-3-hydroxykynurenine + H(2)O → 3-hydroxyanthranilate + L-alanine.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
ARO9
Uniprot ID:
P38840
Molecular weight:
58527.0
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
L-alanine + 2-oxoglutarate = pyruvate + L- glutamate
Gene Name:
ALT2
Uniprot ID:
P52892
Molecular weight:
56769.30078
Reactions
L-alanine + 2-oxoglutarate → pyruvate + L-glutamate.
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
L-alanine + 2-oxoglutarate = pyruvate + L- glutamate
Gene Name:
ALT1
Uniprot ID:
P52893
Molecular weight:
66421.10156
Reactions
L-alanine + 2-oxoglutarate → pyruvate + L-glutamate.
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Plays a role in the turnover of the vacuolar glutathione and in the supply of growth requirements during nitrogen starvation
Gene Name:
ECM38
Uniprot ID:
Q05902
Molecular weight:
73179.79688
Reactions
(5-L-glutamyl)-peptide + an amino acid → peptide + 5-L-glutamyl amino acid.

Transporters

General function:
Involved in transport
Specific function:
Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:
GAP1
Uniprot ID:
P19145
Molecular weight:
65654.89844
General function:
Involved in transport
Specific function:
Can transport glutamate, aspartate, glutamine, asparagine, serine, alanine and glycine
Gene Name:
DIP5
Uniprot ID:
P53388
Molecular weight:
68096.70313
General function:
Involved in transport
Specific function:
Required for high-affinity proline transport. May be responsible for proline recognition and probably also for proline translocation across the plasma membrane. Also function as non- specific GABA permease. Can also transport alanine and glycine
Gene Name:
PUT4
Uniprot ID:
P15380
Molecular weight:
68786.79688
General function:
Involved in transport
Specific function:
Required for high-affinity tryptophan transport. Also transports cysteine, phenyalanine and tyrosine
Gene Name:
TAT2
Uniprot ID:
P38967
Molecular weight:
65403.80078
General function:
Involved in transport
Specific function:
Permease for leucine, valine and isoleucine. Also transports cysteine, methionine, phenyalanine, tyrosine and tryptophan
Gene Name:
BAP2
Uniprot ID:
P38084
Molecular weight:
67669.60156
General function:
Involved in transport
Specific function:
Involved in transport of isoleucine, leucine, valine, cysteine, methionine, phenylalanine, tyrosine and tryptophan
Gene Name:
BAP3
Uniprot ID:
P41815
Molecular weight:
67364.39844
General function:
Involved in transport
Specific function:
Broad substrate range permease which transports asparagine and glutamine with intermediate specificity. Also transports Ala, Cys, Gly, Ile, Leu, Met, Phe, Ser, Thr, Tyr and Val. Important for the utilization of amino acids as a nitrogen source
Gene Name:
AGP1
Uniprot ID:
P25376
Molecular weight:
69670.70313