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3-Aminopropanoic acid (FDB002253)

Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2020-09-17 15:38:14 UTC
Primary IDFDB002253
Secondary Accession Numbers
  • FDB031281
Chemical Information
FooDB Name3-Aminopropanoic acid
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 sweet and odorless tasting compound. Outside of the human body, beta-Alanine is found, on average, in the highest concentration within a few different foods, such as beers, blackcurrants, and garden tomato (var.). beta-Alanine has also been detected, but not quantified in, several different foods, such as apples, bitter gourds, carrots, and sour cherries. This could make beta-alanine a potential biomarker for the consumption of these foods. beta-Alanine is a potentially toxic compound. beta-Alanine, with regard to humans, has been found to be associated with several diseases such as methylmalonate semialdehyde dehydrogenase deficiency, lewy body disease, crohn's disease, and perillyl alcohol administration for cancer treatment; beta-alanine has also been linked to the inborn metabolic disorder dihydropyrimidine dehydrogenase deficiency. A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position.
CAS Number107-95-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H7NO2
IUPAC name3-aminopropanoic acid
InChI IdentifierInChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChI KeyUCMIRNVEIXFBKS-UHFFFAOYSA-N
Isomeric SMILESNCCC(O)=O
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Environmental role:

Industrial application:

Foods

Meats:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-be815b0a56f225da04d82014-09-20View Spectrum
GC-MS3-Aminopropanoic acid, 3 TMS, GC-MS Spectrumsplash10-007k-1920000000-9389ee061bd6e9ae3b22Spectrum
GC-MS3-Aminopropanoic acid, 3 TMS, GC-MS Spectrumsplash10-0fdt-2930000000-5799fddb7fac04d22372Spectrum
GC-MS3-Aminopropanoic acid, 3 TMS, GC-MS Spectrumsplash10-006t-1940000000-49f1b7c80f35cbcf102eSpectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-006t-2920000000-c701f2e5652fa4f35e50Spectrum
GC-MS3-Aminopropanoic acid, 3 TMS, GC-MS Spectrumsplash10-00di-8930000000-c4f8138d4cb7f1ea851aSpectrum
GC-MS3-Aminopropanoic acid, 1 TMS, GC-MS Spectrumsplash10-014i-2900000000-c54f1d5878600393dca7Spectrum
GC-MS3-Aminopropanoic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-1900000000-2f55a09bba074034dee7Spectrum
GC-MS3-Aminopropanoic acid, 3 TMS, GC-MS Spectrumsplash10-00ds-2940000000-4192453eaba2cbecf800Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-006t-1960000000-665868f9adaa275dbdb3Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-007k-1920000000-9389ee061bd6e9ae3b22Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0fdt-2930000000-5799fddb7fac04d22372Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-006t-1940000000-49f1b7c80f35cbcf102eSpectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-006t-2920000000-c701f2e5652fa4f35e50Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-00di-8930000000-c4f8138d4cb7f1ea851aSpectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-00ds-2940000000-4192453eaba2cbecf800Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-2900000000-c54f1d5878600393dca7Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-2f55a09bba074034dee7Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-efc0822e26bcf842e232Spectrum
GC-MS3-Aminopropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0072-2920000000-284cff207c712b6698d6Spectrum
Predicted GC-MS3-Aminopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9000000000-ad7f96b2c6a1f5183794Spectrum
Predicted GC-MS3-Aminopropanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-9700000000-d73baf312b8af27575b3Spectrum
Predicted GC-MS3-Aminopropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Aminopropanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Aminopropanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Aminopropanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-61740a52186a51b8543c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-1bdf967935160468d5502012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0ba5264cfc5ec108718b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-61740a52186a51b8543c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-1bdf967935160468d5502017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-0ba5264cfc5ec108718b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-1c44f6e35a8ed7d36b092021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-799cbaba87e33fa5afde2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-86d934e6151015ddb8102021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dl-9000000000-c30cc77c93e4ec09265a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000j-9000000000-540a52fcec629c0a06472012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000b-9000000000-531b17f8e168962251862012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-c6a2c78d3223284001272012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-d5f47100c42e7777802e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-e8f43be75c153e5be3cc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-1004-9000100000-ccb09493216d97165c8d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00l7-9230000000-644b1dbe52c5f07e285a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-9000000000-ff4a990aa1fb1b7cc33d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-c6a2c78d3223284001272017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-d5f47100c42e7777802e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-e8f43be75c153e5be3cc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-1004-9000100000-ccb09493216d97165c8d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00l7-9230000000-644b1dbe52c5f07e285a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9000000000-ff4a990aa1fb1b7cc33d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9000000000-363393d05fd6a4b823182021-09-20View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).