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Beta-Alanine (YMDB00195)

Identification
YMDB IDYMDB00195
NameBeta-Alanine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionbeta-Alanine, also known as 3-aminopropanoate or bala, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. beta-Alanine is a very strong basic compound (based on its pKa). beta-Alanine exists in all living species, ranging from bacteria to humans. beta-Alanine is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 2-Carboxyethylamine
  • 3-amino-Propanoate
  • 3-amino-Propanoic acid
  • 3-Aminopropanoate
  • 3-Aminopropanoic acid
  • 3-Aminopropionate
  • 3-Aminopropionic acid
  • Abufene
  • B-Alanine
  • b-Aminopropanoate
  • b-Aminopropanoic acid
  • b-Aminopropionate
  • b-Aminopropionic acid
  • beta Alanine
  • beta-Alanine
  • beta-Aminopropanoate
  • beta-Aminopropanoic acid
  • beta-Aminopropionate
  • beta-Aminopropionic acid
  • omega-Aminopropionate
  • omega-Aminopropionic acid
  • BAla
  • H-beta-Ala-OH
  • Β-aminopropionate
  • Β-aminopropionic acid
  • H-b-Ala-OH
  • H-Β-ala-OH
  • Β-alanine
  • 3 Aminopropionic acid
  • β-Aminopropanoic acid
  • omega-Aminopropanoic acid
  • ω-Aminopropanoic acid
  • ω-Aminopropionic acid
CAS number107-95-9
WeightAverage: 89.0932
Monoisotopic: 89.047678473
InChI KeyUCMIRNVEIXFBKS-UHFFFAOYSA-N
InChIInChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
IUPAC Name3-aminopropanoic acid
Traditional IUPAC Nameβ alanine
Chemical FormulaC3H7NO2
SMILES[H]OC(=O)C([H])([H])C([H])([H])N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point200 °C
Experimental Properties
PropertyValueReference
Water Solubility545 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.05 [TSAI,RS ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility494 g/LALOGPS
logP-3.3ALOGPS
logP-3.2ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.7 m³·mol⁻¹ChemAxon
Polarizability8.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB002253
SweetFDB002253
SMPDB Pathways
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pantothenate and CoA biosynthesisec00770 Map00770
Propanoate metabolismec00640 Map00640
Pyrimidine metabolismec00240 Map00240
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
3-Aminopropionaldehyde + water + NADP → Beta-Alanine + hydron + NADPH
Beta-Alanine + (R)-Pantoate + Adenosine triphosphate → Pantothenic acid + Adenosine monophosphate + Pyrophosphate + hydron
L-Aspartic acid + hydron Carbon dioxide + Beta-Alanine
Beta-Alanine + Adenosine triphosphate + (R)-Pantoate → Adenosine monophosphate + Pyrophosphate + hydron + Pantothenic acid
KEGG Reactions
NAD + 3-Aminopropionaldehyde + water → NADH + Beta-Alanine + hydron
Adenosine triphosphate + (R)-Pantoic acid + Beta-Alanine → Adenosine monophosphate + Pyrophosphate + (R)-Pantothenic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-007k-1920000000-9389ee061bd6e9ae3b22JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fdt-2930000000-5799fddb7fac04d22372JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-006t-1940000000-49f1b7c80f35cbcf102eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-006t-2920000000-c701f2e5652fa4f35e50JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-8930000000-c4f8138d4cb7f1ea851aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-014i-2900000000-c54f1d5878600393dca7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1900000000-2f55a09bba074034dee7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00ds-2940000000-4192453eaba2cbecf800JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-1960000000-665868f9adaa275dbdb3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-007k-1920000000-9389ee061bd6e9ae3b22JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fdt-2930000000-5799fddb7fac04d22372JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-1940000000-49f1b7c80f35cbcf102eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-2920000000-c701f2e5652fa4f35e50JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8930000000-c4f8138d4cb7f1ea851aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ds-2940000000-4192453eaba2cbecf800JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2900000000-c54f1d5878600393dca7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1900000000-2f55a09bba074034dee7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-efc0822e26bcf842e232JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0072-2920000000-284cff207c712b6698d6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-ad7f96b2c6a1f5183794JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9700000000-d73baf312b8af27575b3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-61740a52186a51b8543cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-1bdf967935160468d550JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0ba5264cfc5ec108718bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-61740a52186a51b8543cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-1bdf967935160468d550JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-0ba5264cfc5ec108718bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-1c44f6e35a8ed7d36b09JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-799cbaba87e33fa5afdeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-86d934e6151015ddb810JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dl-9000000000-c30cc77c93e4ec09265aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000j-9000000000-540a52fcec629c0a0647JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000b-9000000000-531b17f8e16896225186JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-c6a2c78d322328400127JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-d5f47100c42e7777802eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-e8f43be75c153e5be3ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-1004-9000100000-ccb09493216d97165c8dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00l7-9230000000-644b1dbe52c5f07e285aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-9000000000-ff4a990aa1fb1b7cc33dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-c6a2c78d322328400127JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-d5f47100c42e7777802eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-e8f43be75c153e5be3ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-1004-9000100000-ccb09493216d97165c8dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00l7-9230000000-644b1dbe52c5f07e285aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9000000000-ff4a990aa1fb1b7cc33dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9000000000-363393d05fd6a4b82318JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-be815b0a56f225da04d8JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • White, W. H., Skatrud, P. L., Xue, Z., Toyn, J. H. (2003). "Specialization of function among aldehyde dehydrogenases: the ALD2 and ALD3 genes are required for beta-alanine biosynthesis in Saccharomyces cerevisiae." Genetics 163:69-77.12586697
  • White, W. H., Gunyuzlu, P. L., Toyn, J. H. (2001). "Saccharomyces cerevisiae is capable of de Novo pantothenic acid biosynthesis involving a novel pathway of beta-alanine production from spermine." J Biol Chem 276:10794-10800.11154694
Synthesis Reference:Buc, Saul R.; Ford, Jared H.; Wise, E. C. Improved synthesis of b-alanine. Journal of the American Chemical Society (1945), 67 92-4.
External Links:
ResourceLink
CHEBI ID16958
HMDB IDHMDB00056
Pubchem Compound ID239
Kegg IDC00099
ChemSpider ID234
FOODB IDFDB002253
WikipediaBeta-Alanine
BioCyc IDB-ALANINE

Enzymes

Protein Details
1. Aldehyde dehydrogenase [NAD(P)+] 1
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD2
Uniprot ID:
P47771
Molecular weight:
55187.39844
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
Protein Details
2. Aldehyde dehydrogenase [NAD(P)+] 2
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD3
Uniprot ID:
P54114
Molecular weight:
55384.80078
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
Protein Details
3. Glutamate decarboxylase
General function:
Involved in glutamate decarboxylase activity
Specific function:
L-glutamate = 4-aminobutanoate + CO(2)
Gene Name:
GAD1
Uniprot ID:
Q04792
Molecular weight:
65989.5
Reactions
L-glutamate → 4-aminobutanoate + CO(2).
Protein Details
4. Pantoate--beta-alanine ligase
General function:
Involved in pantoate-beta-alanine ligase activity
Specific function:
Required for pantothenic acid biosynthesis
Gene Name:
PAN6
Uniprot ID:
P40459
Molecular weight:
35031.89844
Reactions
ATP + (R)-pantoate + beta-alanine → AMP + diphosphate + (R)-pantothenate.