Record Information
Version2.0
Creation Date2009-07-23 18:26:07 UTC
Update Date2014-12-24 20:25:57 UTC
Accession NumberT3D3082
Identification
Common Namebeta-Methylamino-L-alanine
ClassSmall Molecule
DescriptionMethylamino-L-alanine,КBMAA, is a non-proteinogenic amino acid produced by cyanobacteria. It is a plant toxin found in the seeds of the cycad (division Cycadophyta). It is produced by cyanobacteria of the genus Nostoc that live on the plant's roots and exibits neurotoxic effects. Acutely, BMAA can act as an excitotoxin on glutamate receptors such as NMDA, calcium dependent AMPA and kainite receptors. The activation of the metabotropic glutamate receptor 5 is believed to induce oxidative stress in the neuron by depletion of glutathione. BMAA is also suggested to misincorporate into nascent proteins in place of L-Serine, possibly causing protein misfolding and aggregation, both hallmarks of tangle diseases, including Alzheimer's, Parkinson's and ALS, PSP and Lewy Body Disease. In-vitro research has shown that protein association of L-BMAA can be inhibited in presence of excess L-Serine. (Wikipedia)
Compound Type
  • Amine
  • Bacterial Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
3-(Methylamino)-L-alanine
3-Methylamino-L-alanine
b-Methylamino-L-alanine
BMAA
L-bmaa
β-Methylamino-L-alanine
Chemical FormulaC4H10N2O2
Average Molecular Mass118.134 g/mol
Monoisotopic Mass118.074 g/mol
CAS Registry Number15920-93-1
IUPAC Name2-amino-3-(methylamino)propanoic acid
Traditional Name3-(methylamino)-(DL)-alanine
SMILESCNCC(N)C(O)=O
InChI IdentifierInChI=1S/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)
InChI KeyInChIKey=UJVHVMNGOZXSOZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Central Nervous System
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility275 g/LALOGPS
logP-3.2ALOGPS
logP-3.8ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.35 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.47 m³·mol⁻¹ChemAxon
Polarizability11.95 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-723c43f86fac93138d592021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rf-9300000000-e8cc67e99f8392f030792016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-2a99e5543703f59a60b42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-45a7801287a3f96b30d62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-f1d1f230db250f1667072016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9700000000-a72edffd3071d783a73e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007x-9000000000-0330bca304c61e32681b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-8900000000-47a4739a7db5fa52bfc12021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9000000000-0657b74281268f49b22e2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-942f1b1aaa14f67379b32021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-76f78092b136dbfaef3d2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-913082641e0856b80db92021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8b5a890d1e3276284ef92021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityBMAA may cause neurotoxic effects by damaging cells (such as neurons) in the motor cortex and spinal cord. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMethylamino-L-alanine, beta- is a plant toxin found in the seeds of the cycad (division Cycadophyta). (1)
Minimum Risk LevelNot Available
Health EffectsBMAA is considered a possible cause of the amyotrophic lateral sclerosis/parkinsonism-dementia complex (ALS/PDC). Its neurotoxic effects may include degenerative locomotor diseases resulting from damage to cells (such as neurons) in the motor cortex and spinal cord. (1)
SymptomsSymptoms of BMAA exposure may include limb muscle atrophy and behavioral dysfunction. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID105089
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC08291
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMethylamino-L-alanine, beta-
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wikipedia. beta-Methylamino-L-alanine. Last Updated 9 March 2009. [Link]
  2. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available