NP-MRD: Showing NP-Card for β-N-methylamino-L-alanine (NP0004982)

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Record Information

Version

1.0

Created at

2020-12-09 02:21:40 UTC

Updated at

2021-07-15 16:50:43 UTC

NP-MRD ID

NP0004982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-N-methylamino-L-alanine

Provided By

NPAtlas

Description

L-BMAA is also known as BMAA. L-BMAA is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. β-N-methylamino-L-alanine is found in Cycas micronesica, Cycas revoluta and Nostoc sp.. It was first documented in 2003 (PMID: 14612559). Based on a literature review a significant number of articles have been published on L-BMAA (PMID: 33190068) (PMID: 32922737) (PMID: 32585217) (PMID: 32380192).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118153D          

 18 17  0  0  0  0            999 V2000
    2.6824   -0.2062   -0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4538   -0.0493    0.5101 N   0  0  1  0  0  0  0  0  0  0  0  0
    0.3696    0.2929   -0.3938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9184    0.4497    0.4103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1977   -0.7972    1.0708 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0345    0.7678   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0088    1.8139   -1.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178   -0.0797   -0.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.6041    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5386   -0.1881   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1982   -1.1629    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309   -0.8523    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2390   -0.5236   -1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063    1.2118   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    1.2572    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347   -1.5945    0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -0.9397    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9509   -0.0038   -0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  4 15  1  1  0  0  0
  5 16  1  0  0  0  0
  5 17  1  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])N([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)/t3-/m0/s1

> <INCHI_KEY>
UJVHVMNGOZXSOZ-VKHMYHEASA-N

> <FORMULA>
C4H10N2O2

> <MOLECULAR_WEIGHT>
118.136

> <EXACT_MASS>
118.07422757

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.843856196443065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(methylamino)propanoic acid

> <ALOGPS_LOGP>
-3.18

> <JCHEM_LOGP>
-3.7745398217683204

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.956561175746038

> <JCHEM_PKA_STRONGEST_BASIC>
9.85849128456775

> <JCHEM_POLAR_SURFACE_AREA>
75.35

> <JCHEM_REFRACTIVITY>
28.473100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.75e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-methylamino-L-alanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.682  -0.206  -0.206  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.454  -0.049   0.510  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.370   0.293  -0.394  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.918   0.450   0.410  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.198  -0.797   1.071  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.034   0.768  -0.516  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.009   1.814  -1.203  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.118  -0.080  -0.638  0.00  0.00           O+0
HETATM    9  H   UNK     0       3.392   0.604   0.062  0.00  0.00           H+0
HETATM   10  H   UNK     0       2.539  -0.188  -1.305  0.00  0.00           H+0
HETATM   11  H   UNK     0       3.198  -1.163   0.094  0.00  0.00           H+0
HETATM   12  H   UNK     0       1.231  -0.852   1.116  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.239  -0.524  -1.130  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.606   1.212  -0.950  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.811   1.257   1.150  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.035  -1.595   0.435  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.638  -0.940   1.929  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.951  -0.004  -0.076  0.00  0.00           H+0
CONECT    1    2    9   10   11                                             
CONECT    2    1    3   12                                                  
CONECT    3    2    4   13   14                                             
CONECT    4    3    5    6   15                                             
CONECT    5    4   16   17                                                  
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   18                                                       
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    5                                                            
CONECT   17    5                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
beta-N-Methylamino-L-alanine	ChEBI
BMAA	ChEBI
L-alpha-Amino-beta-(methylamino)propanoic acid	ChEBI
L-alpha-Amino-beta-(methylamino)propionic acid	ChEBI
b-N-Methylamino-L-alanine	Generator
Β-N-methylamino-L-alanine	Generator
L-a-Amino-b-(methylamino)propanoate	Generator
L-a-Amino-b-(methylamino)propanoic acid	Generator
L-alpha-Amino-beta-(methylamino)propanoate	Generator
L-Α-amino-β-(methylamino)propanoate	Generator
L-Α-amino-β-(methylamino)propanoic acid	Generator
L-a-Amino-b-(methylamino)propionate	Generator
L-a-Amino-b-(methylamino)propionic acid	Generator
L-alpha-Amino-beta-(methylamino)propionate	Generator
L-Α-amino-β-(methylamino)propionate	Generator
L-Α-amino-β-(methylamino)propionic acid	Generator
2-Amino-3(methylamino)propionic acid	MeSH
alpha-Amino-beta-methylaminopropionate	MeSH
beta-Methylamino-L-alanine	MeSH
L-BMAA	MeSH

Chemical Formula

C₄H₁₀N₂O₂

Average Mass

118.1360 Da

Monoisotopic Mass

118.07423 Da

IUPAC Name

(2S)-2-amino-3-(methylamino)propanoic acid

Traditional Name

β-methylamino-L-alanine

CAS Registry Number

Not Available

SMILES

CNC[C@H](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)/t3-/m0/s1

InChI Key

UJVHVMNGOZXSOZ-VKHMYHEASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cycas circinalis	KNApSAcK Database	22123792
Cycas micronesica	Plant	KNApSAcK
Cycas revoluta	LOTUS Database	35616633
Nostoc sp.	NPAtlas	14612559

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
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	11.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA027398

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001380

Chemspider ID

94816

KEGG Compound ID

C08291

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

BMAA

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

73169

Good Scents ID

Not Available

References

General References

Cox PA, Banack SA, Murch SJ: Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam. Proc Natl Acad Sci U S A. 2003 Nov 11;100(23):13380-3. doi: 10.1073/pnas.2235808100. [PubMed:14612559 ]
Spencer PS, Palmer VS, Kisby GE: Western Pacific ALS-PDC: Evidence implicating cycad genotoxins. J Neurol Sci. 2020 Dec 15;419:117185. doi: 10.1016/j.jns.2020.117185. Epub 2020 Oct 15. [PubMed:33190068 ]
Nunn PB, Codd GA: Environmental distribution of the neurotoxin l-BMAA in Paenibacillus species. Toxicol Res (Camb). 2019 Oct 3;8(6):781-783. doi: 10.1039/c9tx00203k. eCollection 2019 Nov 1. [PubMed:32922737 ]
Schneider T, Simpson C, Desai P, Tucker M, Lobner D: Neurotoxicity of isomers of the environmental toxin L-BMAA. Toxicon. 2020 Sep;184:175-179. doi: 10.1016/j.toxicon.2020.06.014. Epub 2020 Jun 23. [PubMed:32585217 ]
Carion A, Markey A, Hetru J, Carpentier C, Suarez-Ulloa V, Denoel M, Earley RL, Silvestre F: Behavior and gene expression in the brain of adult self-fertilizing mangrove rivulus fish (Kryptolebias marmoratus) after early life exposure to the neurotoxin beta-N-methylamino-l-alanine (BMAA). Neurotoxicology. 2020 Jul;79:110-121. doi: 10.1016/j.neuro.2020.04.007. Epub 2020 May 5. [PubMed:32380192 ]

Showing NP-Card for β-N-methylamino-L-alanine (NP0004982)

MOL for NP0004982 (β-N-methylamino-L-alanine)

3D MOL for NP0004982 (β-N-methylamino-L-alanine)

3D SDF for NP0004982 (β-N-methylamino-L-alanine)

3D-SDF for NP0004982 (β-N-methylamino-L-alanine)

PDB for NP0004982 (β-N-methylamino-L-alanine)

3D PDB for NP0004982 (β-N-methylamino-L-alanine)

SMILES for NP0004982 (β-N-methylamino-L-alanine)

INCHI for NP0004982 (β-N-methylamino-L-alanine)

Structure for NP0004982 (β-N-methylamino-L-alanine)

3D Structure for NP0004982 (β-N-methylamino-L-alanine)