Showing metabocard for Betaine (MMDBc0000012)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:24:43 UTC
Update Date2024-10-13 09:10:19 UTC
Metabolite IDMMDBc0000012
Metabolite Identification
Common NameBetaine
DescriptionBetaine (CAS: 107-43-7), also known as N,N,N-trimethylglycine, was named after its discovery in sugar beet (Beta vulgaris) in the 19th century. It is a small N-trimethylated amino acid, existing in zwitterionic form at neutral pH. It is now often called glycine betaine to distinguish it from other betaines that are widely distributed in microorganisms, plants, and animals. Many naturally occurring betaines serve as organic osmolytes, substances synthesized or taken up from the environment by cells for protection against osmotic stress, drought, high salinity, or high temperature. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration (Wikipedia). Betaine functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. In particular, it methylates homocysteine to methionine, also producing N,N-dimethylglycine. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine comes from either the diet or by the oxidation of choline. Betaine insufficiency is associated with metabolic syndrome, lipid disorders, and diabetes, and may have a role in vascular and other diseases (PMID: 20346934 ). Betaine is important in development, from the pre-implantation embryo to infancy. Betaine is also widely regarded as an anti-oxidant. Betaine has been shown to have an inhibitory effect on NO release in activated microglial cells and may be an effective therapeutic component to control neurological disorders (PMID: 22801281 ). As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances (Martindale, The Extra Pharmacopoeia, 30th Ed, p1341).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5380de14c8>

  Mrv1652307172023112D          

  8  7  0  0  0  0            999 V2000
    1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
M  CHG  1   2   1
M  END
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3D MOL for #<Metabolite:0x00007f5380de14c8>

HMDB0000043
     RDKit          3D
Betaine
 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.2244   -1.4792   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5044   -0.0854   -0.0967 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6546    0.2771   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093    0.2771    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740    0.6588   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508    0.2029    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.6824    1.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763    0.7946   -0.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830   -1.6593   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -1.9448    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.9751   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5369   -0.2407   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976    1.3738   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.1447   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625    1.1142    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.6391    1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -0.5480    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.4025   -1.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    1.7512   -0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6302    1.2684    0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  CHG  1   2   1
M  END
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3D SDF for #<Metabolite:0x00007f5380de14c8>

  Mrv1652307172023112D          

  8  7  0  0  0  0            999 V2000
    1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
MMDBc0000012

> <DATABASE_NAME>
MIME

> <SMILES>
C[N+](C)(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1

> <INCHI_KEY>
KWIUHFFTVRNATP-UHFFFAOYSA-O

> <FORMULA>
C5H12NO2

> <MOLECULAR_WEIGHT>
118.1543

> <EXACT_MASS>
118.086803633

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
12.522298635930067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(carboxymethyl)trimethylazanium

> <ALOGPS_LOGP>
-2.12

> <JCHEM_LOGP>
-4.494183842471745

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2595637800263866

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
41.9863

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl glycine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f5380de14c8>

HMDB0000043
     RDKit          3D
Betaine
 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.2244   -1.4792   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5044   -0.0854   -0.0967 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6546    0.2771   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093    0.2771    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740    0.6588   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508    0.2029    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.6824    1.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763    0.7946   -0.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830   -1.6593   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -1.9448    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.9751   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5369   -0.2407   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976    1.3738   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.1447   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625    1.1142    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.6391    1.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -0.5480    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.4025   -1.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    1.7512   -0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6302    1.2684    0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
M  CHG  1   2   1
M  END
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PDB for #<Metabolite:0x00007f5380de14c8>

HEADER    PROTEIN                                 17-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-20         0                                  
HETATM    1  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      -1.334   0.000   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.104   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.564  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4    5    6                                             
CONECT    3    2    7                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    1    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x00007f5380de14c8>

COMPND    HMDB0000043
HETATM    1  C1  UNL     1      -0.224  -1.479  -0.278  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.504  -0.085  -0.097  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.655   0.277  -0.916  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.809   0.277   1.261  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.674   0.659  -0.539  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.851   0.203   0.218  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.819  -0.682   1.095  1.00  0.00           O  
HETATM    8  O2  UNL     1       3.076   0.795  -0.060  1.00  0.00           O  
HETATM    9  H1  UNL     1       0.683  -1.659  -0.903  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.118  -1.945   0.743  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.069  -1.975  -0.837  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.537  -0.241  -0.446  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.798   1.374  -0.966  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.576  -0.145  -1.939  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.563   1.114   1.254  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.041   0.639   1.842  1.00  0.00           H  
HETATM   17  H9  UNL     1      -1.302  -0.548   1.826  1.00  0.00           H  
HETATM   18  H10 UNL     1       0.866   0.402  -1.619  1.00  0.00           H  
HETATM   19  H11 UNL     1       0.513   1.751  -0.504  1.00  0.00           H  
HETATM   20  H12 UNL     1       3.630   1.268   0.637  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    4    5
CONECT    3   12   13   14
CONECT    4   15   16   17
CONECT    5    6   18   19
CONECT    6    7    7    8
CONECT    8   20
END
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SMILES for #<Metabolite:0x00007f5380de14c8>

C[N+](C)(C)CC(O)=O
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INCHI for #<Metabolite:0x00007f5380de14c8>

InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1
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Synonyms
Molecular FormulaC5H12NO2
Average Mass118.1543
Monoisotopic Mass118.086803633
IUPAC Name(carboxymethyl)trimethylazanium
Traditional Nametrimethyl glycine
CAS Registry Number6915-17-9
SMILES
C[N+](C)(C)CC(O)=O
InChI Identifier
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1
InChI KeyKWIUHFFTVRNATP-UHFFFAOYSA-O