Showing metabocard for beta-Alanine (MMDBc0000018)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:24:57 UTC
Update Date2022-08-30 23:03:38 UTC
Metabolite IDMMDBc0000018
Metabolite Identification
Common Namebeta-Alanine
Descriptionbeta-Alanine is the only naturally occurring beta-amino acid - an amino acid in which the amino group is at the beta-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. beta-Alanine can undergo a transanimation reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, beta-alanine may act as a false transmitter replacing gamma-aminobutyric acid. When present in sufficiently high levels, beta-alanine can act as a neurotoxin, a mitochondrial toxin, and a metabotoxin. A neurotoxin is a compound that damages the brain or nerve tissue. A mitochondrial toxin is a compound that damages mitochondria and reduces cellular respiration as well as oxidative phosphorylation. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of beta-alanine are associated with at least three inborn errors of metabolism, including GABA-transaminase deficiency, hyper-beta-alaninemia, and methylmalonate semialdehyde dehydrogenase deficiency. beta-Alanine is a central nervous system (CNS) depressant and is an inhibitor of GABA transaminase. The associated inhibition of GABA transaminase and displacement of GABA from CNS binding sites can also lead to GABAuria (high levels of GABA in the urine) and convulsions. In addition to its neurotoxicity, beta-alanine reduces cellular levels of taurine, which are required for normal respiratory chain function. Cellular taurine depletion is known to reduce respiratory function and elevate mitochondrial superoxide generation, which damages mitochondria and increases oxidative stress (PMID: 27023909 ). Individuals suffering from mitochondrial defects or mitochondrial toxicity typically develop neurotoxicity, hypotonia, respiratory distress, and cardiac failure. beta-Alanine is a biomarker for the consumption of meat, especially red meat.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000055d24adebc38>


  Mrv1652309272007332D          

  6  5  0  0  0  0            999 V2000
    1.1041    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041    1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.1874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  2  0  0  0  0
  3  1  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000055d24adebc38>

HMDB0000056
     RDKit          3D
beta-Alanine
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.7109    0.3637    0.5744 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0442   -0.5095   -0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -0.6359   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    0.6597   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876    1.6835   -0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914    0.7158   -0.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1262    0.7934    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.9479    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -1.5404   -0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617   -0.2503   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.1606    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -1.2717   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983    0.2043    0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  6 13  1  0
M  END
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3D SDF for #<Metabolite:0x000055d24adebc38>


  Mrv1652309272007332D          

  6  5  0  0  0  0            999 V2000
    1.1041    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041    1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.1874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  2  0  0  0  0
  3  1  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000018

> <DATABASE_NAME>
MIME

> <SMILES>
NCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)

> <INCHI_KEY>
UCMIRNVEIXFBKS-UHFFFAOYSA-N

> <FORMULA>
C3H7NO2

> <MOLECULAR_WEIGHT>
89.0932

> <EXACT_MASS>
89.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.617827871827803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-aminopropanoic acid

> <ALOGPS_LOGP>
-3.26

> <JCHEM_LOGP>
-3.173589452576714

> <ALOGPS_LOGS>
0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.084398800362644

> <JCHEM_PKA_STRONGEST_BASIC>
10.307201201262663

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
20.7028

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β alanine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x000055d24adebc38>

HMDB0000056
     RDKit          3D
beta-Alanine
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.7109    0.3637    0.5744 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0442   -0.5095   -0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -0.6359   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    0.6597   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876    1.6835   -0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914    0.7158   -0.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1262    0.7934    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.9479    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -1.5404   -0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617   -0.2503   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.1606    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -1.2717   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983    0.2043    0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  6 13  1  0
M  END
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PDB for #<Metabolite:0x000055d24adebc38>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       2.061   0.420   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.395  -0.350   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.727  -0.350   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.061   1.960   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.728   0.420   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.062  -0.350   0.000  0.00  0.00           N+0
CONECT    1    2    4    3                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for #<Metabolite:0x000055d24adebc38>

COMPND    HMDB0000056
HETATM    1  N1  UNL     1       1.711   0.364   0.574  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.044  -0.509  -0.333  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.441  -0.636  -0.087  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.134   0.660  -0.200  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.488   1.684  -0.470  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.491   0.716  -0.004  1.00  0.00           O  
HETATM    7  H1  UNL     1       1.126   0.793   1.302  1.00  0.00           H  
HETATM    8  H2  UNL     1       2.453   0.948   0.177  1.00  0.00           H  
HETATM    9  H3  UNL     1       1.474  -1.540  -0.180  1.00  0.00           H  
HETATM   10  H4  UNL     1       1.262  -0.250  -1.383  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.685  -1.161   0.834  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.832  -1.272  -0.935  1.00  0.00           H  
HETATM   13  H7  UNL     1      -2.998   0.204   0.704  1.00  0.00           H  
CONECT    1    2    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5    5    6
CONECT    6   13
END
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SMILES for #<Metabolite:0x000055d24adebc38>

NCCC(O)=O
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INCHI for #<Metabolite:0x000055d24adebc38>

InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
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Synonyms
ValueSource
3-Aminopropanoic acidChEBI
3-Aminopropionic acidChEBI
BAlaChEBI
beta-Aminopropionic acidChEBI
H-beta-Ala-OHChEBI
Omega-aminopropionic acidChEBI
3-AminopropanoateKegg
AbufeneKegg
3-AminopropionateGenerator
b-AminopropionateGenerator
b-Aminopropionic acidGenerator
beta-AminopropionateGenerator
Β-aminopropionateGenerator
Β-aminopropionic acidGenerator
H-b-Ala-OHGenerator
H-Β-ala-OHGenerator
Omega-aminopropionateGenerator
b-AlanineGenerator
Β-alanineGenerator
2-CarboxyethylamineHMDB
3-Amino-propanoateHMDB
3-Amino-propanoic acidHMDB
b-AminopropanoateHMDB
b-Aminopropanoic acidHMDB
beta AlanineHMDB
beta-AminopropanoateHMDB
beta-Aminopropanoic acidHMDB
3 Aminopropionic acidHMDB
β-Aminopropanoic acidPhytoBank
omega-Aminopropanoic acidPhytoBank
ω-Aminopropanoic acidPhytoBank
ω-Aminopropionic acidPhytoBank
beta-AlaninePhytoBank
Molecular FormulaC3H7NO2
Average Mass89.0932
Monoisotopic Mass89.047678473
IUPAC Name3-aminopropanoic acid
Traditional Nameβ alanine
CAS Registry Number107-95-9
SMILES
NCCC(O)=O
InChI Identifier
InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChI KeyUCMIRNVEIXFBKS-UHFFFAOYSA-N