Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2017-10-04 21:59:32 UTC
Primary IDFDB002253
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Aminopropanoic acid
DescriptionWidely distributed in plants including algae, fungi and many higher plants. Flavouring ingredient Beta-alanine is the only naturally occurring beta-amino acid - the amino group is at the β-position from the carboxylate group. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (Vitamin B-5) which itself is a component of coenzyme A. Under normal conditions, beta-alanine is metabolized into acetic acid. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, the compound may be a false transmitter replacing gamma-aminobutyric acid. A rare genetic disorder, hyper-beta-alaninemia, has been reported.; Even though much weaker than glycine (and thus with a debated role as a physiological transmitter), ?-alanine is an agonist next in activity to the cognate ligant glycine itself, for strychnine-sensitive inhibitory glycine receptors (GlyRs) (the agonist order: glycine >> ?-alanine > taurine >> alanine, L-serine > proline).; L-Histidine, with a pKa of 6.1 is a relatively weak buffer over the physiological intramuscular pH range. However, when bound to other amino acids this increases nearer to 6.8-7.0. In particular, when bound to ?-alanine the pKa value is 6.83, making this a very efficient intramuscular buffer. Furthermore, because of the position of the beta amino group, ?-alanine dipeptides are not incorporated proteins and thus can be stored at relatively high concentrations (millimolar). Occurring at 17-25 mmol/kg (dry muscle), carnosine (?-alanyl-L-histidine) is an important intramuscular buffer, constituting 10-20% of the total buffering capacity in type I and II muscle fibres.; ?-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which are amino acids in which the amino group is at the ?-position from the carboxylate group (i.e., two atoms away, see Figure 1). The IUPAC name for ?-alanine would be 3-aminopropanoic acid. Unlike its normal counterpart, L-?-alanine, ?-alanine has no chiral center.; ?-Alanine is not used in the biosynthesis of any major proteins or enzymes. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B5) which itself is a component of coenzyme A. Under normal conditions, ?-alanine is metabolized into acetic acid. Beta-alanine is a biomarker for the consumption of meat, especially red meat.
CAS Number107-95-9
Structure
Thumb
Synonyms
SynonymSource
β-alaninebiospider
β-aminopropionic acidbiospider
«omega»-aminopropionic acidbiospider
2-Carboxyethylaminebiospider
3-amino-Propanoatebiospider
3-amino-Propanoic acidbiospider
3-Aminopropanoatebiospider
3-Aminopropionatebiospider
3-Aminopropionic acidbiospider
Abufenebiospider
Abufene (TN)biospider
Alanine, βbiospider
Alanine, betabiospider
Alanine, beta-biospider
B-alaninebiospider
b-Alanine, 9CIdb_source
B-aminopropanoatebiospider
B-aminopropanoic acidbiospider
B-aminopropionatebiospider
B-aminopropionic acidbiospider
BALbiospider
BAlaChEBI
Beta alaninebiospider
Beta-alabiospider
Beta-alaninebiospider
beta-Alanine (6CI,8CI,9CI)biospider
beta-Alanine-beta-14Cbiospider
Beta-aminopropanoatebiospider
Beta-aminopropanoic acidbiospider
Beta-aminopropionatebiospider
Beta-aminopropionic acidbiospider
FEMA 3252db_source
H-b-Ala-OHGenerator
H-beta-Ala-OHChEBI
H-β-ala-OHGenerator
H2NCH2CH2COOHbiospider
Omega-aminopropionatebiospider
Omega-aminopropionic acidbiospider
Propanoic acid, 3-amino-biospider
β-alanineGenerator
β-aminopropionateGenerator
β-aminopropionic acidGenerator
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
Chemical FormulaC3H7NO2
IUPAC name3-aminopropanoic acid
InChI IdentifierInChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChI KeyInChIKey=UCMIRNVEIXFBKS-UHFFFAOYSA-N
Isomeric SMILESNCCC(O)=O
Average Molecular Weight89
Monoisotopic Molecular Weight89
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.44%; H 7.92%; N 15.72%; O 35.92%DFC
Melting PointMp 200° (197-198°)DFC
Boiling PointNot Available
Experimental Water Solubility545 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.05TSAI,RS ET AL. (1991)
Experimental pKapKa2 10.1 (30°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-007k-1920000000-9389ee061bd6e9ae3b22View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fdt-2930000000-5799fddb7fac04d22372View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-006t-1940000000-49f1b7c80f35cbcf102eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-006t-2920000000-c701f2e5652fa4f35e50View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-8930000000-c4f8138d4cb7f1ea851aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-014i-2900000000-c54f1d5878600393dca7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1900000000-2f55a09bba074034dee7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00ds-2940000000-4192453eaba2cbecf800View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-1960000000-665868f9adaa275dbdb3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-007k-1920000000-9389ee061bd6e9ae3b22View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fdt-2930000000-5799fddb7fac04d22372View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-1940000000-49f1b7c80f35cbcf102eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-2920000000-c701f2e5652fa4f35e50View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8930000000-c4f8138d4cb7f1ea851aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ds-2940000000-4192453eaba2cbecf800View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2900000000-c54f1d5878600393dca7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1900000000-2f55a09bba074034dee7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-efc0822e26bcf842e232View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0072-2920000000-284cff207c712b6698d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-ad7f96b2c6a1f5183794View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9700000000-d73baf312b8af27575b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dl-9000000000-c30cc77c93e4ec09265aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000j-9000000000-540a52fcec629c0a0647View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000b-9000000000-531b17f8e16896225186View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-61740a52186a51b8543cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-1bdf967935160468d550View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0ba5264cfc5ec108718bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-c6a2c78d322328400127View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-d5f47100c42e7777802eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-e8f43be75c153e5be3ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-1004-9000100000-ccb09493216d97165c8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00l7-9230000000-644b1dbe52c5f07e285aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-9000000000-ff4a990aa1fb1b7cc33dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-61740a52186a51b8543cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-3ac278f3f0cfc3d50ebfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-6d6e140cf4317b214296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-9000000000-ead5967d7f21631b6fc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-91312dd333b1413fa045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007c-9000000000-caef7f2a75815a584747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdo-9000000000-5642be49ea98b530ff09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-3ac278f3f0cfc3d50ebfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-6d6e140cf4317b214296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-9000000000-ead5967d7f21631b6fc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-91312dd333b1413fa045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007c-9000000000-caef7f2a75815a584747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdo-9000000000-5642be49ea98b530ff09View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-be815b0a56f225da04d8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID234
ChEMBL IDCHEMBL297569
KEGG Compound IDC00099
Pubchem Compound ID239
Pubchem Substance IDNot Available
ChEBI ID16958
Phenol-Explorer IDNot Available
DrugBank IDDB03107
HMDB IDHMDB00056
CRC / DFC (Dictionary of Food Compounds) IDCHQ52-J:CHQ52-J
EAFUS ID68
Dr. Duke IDBETA-ALANINE
BIGG ID33848
KNApSAcK IDC00001333
HET IDBAL
Flavornet IDNot Available
GoodScent IDrw1002211
SuperScent ID239
Wikipedia IDbeta-Alanine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
avicide33289 A substance used to destroy bird pests (class Aves).DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
Enzymes
NameGene NameUniProt ID
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Glutamate decarboxylase 2GAD2Q05329
Glutamate decarboxylase 1GAD1Q99259
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067 map00250
Beta-Alanine MetabolismSMP00007 map00410
Propanoate MetabolismSMP00016 map00640
Pyrimidine MetabolismSMP00046 map00240
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).