T3DB: beta-Methylamino-L-alanine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation XML

Record Information

Version

2.0

Creation Date

2009-07-23 18:26:07 UTC

Update Date

2014-12-24 20:25:57 UTC

Accession Number

T3D3082

Identification

Common Name

beta-Methylamino-L-alanine

Class

Small Molecule

Description

Methylamino-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

MOL SDF PDB SMILES InChI

Synonyms

Synonym
3-(Methylamino)-L-alanine
3-Methylamino-L-alanine
b-Methylamino-L-alanine
BMAA
L-bmaa
β-Methylamino-L-alanine

Chemical Formula

C₄H₁₀N₂O₂

Average Molecular Mass

118.134 g/mol

Monoisotopic Mass

118.074 g/mol

CAS Registry Number

15920-93-1

IUPAC Name

2-amino-3-(methylamino)propanoic acid

Traditional Name

3-(methylamino)-(DL)-alanine

SMILES

CNCC(N)C(O)=O

InChI Identifier

InChI=1S/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)

InChI Key

InChIKey=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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Central Nervous System

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	275 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.8	ChemAxon
logS	0.37	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.47 m³·mol⁻¹	ChemAxon
Polarizability	11.95 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-723c43f86fac93138d59	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00rf-9300000000-e8cc67e99f8392f03079	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-2a99e5543703f59a60b4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-45a7801287a3f96b30d6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-f1d1f230db250f166707	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9700000000-a72edffd3071d783a73e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007x-9000000000-0330bca304c61e32681b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-8900000000-47a4739a7db5fa52bfc1	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9000000000-0657b74281268f49b22e	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-942f1b1aaa14f67379b3	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-76f78092b136dbfaef3d	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-913082641e0856b80db9	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-8b5a890d1e3276284ef9	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-12	View Spectrum

Toxicity Profile

Route of Exposure

Oral (ingestion) (2) ; dermal (2)

Mechanism of Toxicity

BMAA may cause neurotoxic effects by damaging cells (such as neurons) in the motor cortex and spinal cord. (1)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Methylamino-L-alanine, beta- is a plant toxin found in the seeds of the cycad (division Cycadophyta). (1)

Minimum Risk Level

Not Available

Health Effects

BMAA 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)

Symptoms

Symptoms of BMAA exposure may include limb muscle atrophy and behavioral dysfunction. (1)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

105089

ChEMBL ID

Not Available

ChemSpider ID

Not Available

KEGG ID

C08291

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Methylamino-L-alanine, beta-

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Wikipedia. beta-Methylamino-L-alanine. Last Updated 9 March 2009. [Link]
Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

beta-Methylamino-L-alanine (T3D3082)

Structure for T3D3082: beta-Methylamino-L-alanine