Np mrd loader

Showing NP-Card for Betaine (NP0001442)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-04-19 09:49:47 UTC
NP-MRD IDNP0001442
Secondary Accession NumbersNone
Natural Product Identification
Common NameBetaine
DescriptionBetaine (or 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001442 (Betaine)


  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
Download

3D MOL for NP0001442 (Betaine)

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
Download

3D SDF for NP0001442 (Betaine)


  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>
NP0001442

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001442 (Betaine)

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
Download

PDB for NP0001442 (Betaine)

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
Download

3D PDB for NP0001442 (Betaine)

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
Download

SMILES for NP0001442 (Betaine)

C[N+](C)(C)CC(O)=O
Download

INCHI for NP0001442 (Betaine)

InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3/p+1
Download
View in JSmol
Synonyms
ValueSource
TRIMETHYL glycineChEBI
Trimethylammonioacetic acidGenerator, HMDB
AcidinPepsinMeSH, HMDB
Betaine hydrochlorideMeSH, HMDB
Betaine orphan brandMeSH, HMDB
C.B.B.MeSH, HMDB
scorbo-BétaïneMeSH, HMDB
Stea-16MeSH, HMDB
Acidin-pepsinMeSH, HMDB
Byk brand OF betaine phosphateMeSH, HMDB
Citrate de bétaïne beaufourMeSH, HMDB
Citrate de bétaïne upsaMeSH, HMDB
CystadaneMeSH, HMDB
Fournier brand OF betaine ascorbate and hydrateMeSH, HMDB
LycineMeSH, HMDB
Stea16MeSH, HMDB
Beaufour brand OF betaine citrateMeSH, HMDB
Betaine, glycineMeSH, HMDB
Boizot brand OF betaine aspartateMeSH, HMDB
Glycine betaineMeSH, HMDB
HepastylMeSH, HMDB
Logeais brand OF betaine cyclobutyrateMeSH, HMDB
NovobetaineMeSH, HMDB
ScorbobétaïneMeSH, HMDB
UPSA brand OF betaine citrateMeSH, HMDB
Acidin pepsinMeSH, HMDB
BetaineMeSH, HMDB
Hydrochloride, betaineMeSH, HMDB
Orphan brand OF betaineMeSH, HMDB
OxyneurineMeSH, HMDB
scorbo BétaïneMeSH, HMDB
Stea 16MeSH
N,N,N-TrimethylglycineHMDB
TrimethylaminoacetateHMDB
TrimethylammonioacetateHMDB
Chemical FormulaC5H11NO2
Average Mass117.1463 Da
Monoisotopic Mass117.07898 Da
IUPAC Name(carboxymethyl)trimethylazanium
Traditional Nametrimethyl glycine
CAS Registry Number107-43-7
SMILES
C[N+](C)(C)CC([O-])=O
InChI Identifier
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
InChI KeyKWIUHFFTVRNATP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-19View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-01-19View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)V.dorna832021-09-06View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-12View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Achillea alpinaLOTUS Database
Achillea millefoliumLOTUS Database
Achyranthes asperaPlant
Achyranthes bidentataPlant
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Ailuropoda melanoleucaLOTUS Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amaranthus hypochondriacusLOTUS Database
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Atriplex halimusLOTUS Database
Atriplex spongiosaPlant
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Avicennia marinaPlant
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Blepharis linariifoliaLOTUS Database
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaPlant
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium botrysLOTUS Database
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cistanche salsaLOTUS Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Cola acuminataPlant
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Combretum micranthumLOTUS Database
Corchorus olitoriusFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Delesseria sanguineaLOTUS Database
Desmarestia viridisLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eranthemum pulchellumLOTUS Database
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Homo sapiens (Serum)Animalia
Homo sapiens (Urine)Animalia
Hordeum vulgareFooDB
Hylocereus ocamponisPlant
Hylocereus purpusiiPlant
Hylocereus undatusPlant
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Justicia pectoralisLOTUS Database
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lates calcariferLOTUS Database
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lycium chinenseLOTUS Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus bombycisLOTUS Database
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Neptunea antiquaLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Pseudo-nitzschia multistriataLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Ramalina fraxineaLOTUS Database
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salicornia bigeloviiLOTUS Database
Salicornia rubraLOTUS Database
Salix pulchraFooDB
Salmo salarFooDB
Salsola collinaLOTUS Database
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sida spinosaPlant
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stenodus leucichthysFooDB
Struthio camelusFooDB
Suaeda maritimaLOTUS Database
Suaeda vermiculataLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Synechococcus elongatusLOTUS Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
Thalassiosira pseudonanaLOTUS Database
ThelespermaFooDB
Thunbergia mysorensisLOTUS Database
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Torilis japonicaLOTUS Database
Tragopogon porrifoliusFooDB
Trametes VersicolorLOTUS Database
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point293 - 301 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility611 mg/mL at 19 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.86 g/LALOGPS
logP-2.1ALOGPS
logP-4.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.99 m³·mol⁻¹ChemAxon
Polarizability12.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059606
DrugBank IDDB04455
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID243
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID41139
Good Scents IDNot Available
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Surtees R, Bowron A, Leonard J: Cerebrospinal fluid and plasma total homocysteine and related metabolites in children with cystathionine beta-synthase deficiency: the effect of treatment. Pediatr Res. 1997 Nov;42(5):577-82. [PubMed:9357926 ]
  3. Holm PI, Ueland PM, Kvalheim G, Lien EA: Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry. Clin Chem. 2003 Feb;49(2):286-94. [PubMed:12560353 ]
  4. Knopman D, Patterson M: An open-label, 24-week pilot study of the methyl donor betaine in Alzheimer disease patients. Alzheimer Dis Assoc Disord. 2001 Jul-Sep;15(3):162-5. [PubMed:11522934 ]
  5. Schwahn BC, Chen Z, Laryea MD, Wendel U, Lussier-Cacan S, Genest J Jr, Mar MH, Zeisel SH, Castro C, Garrow T, Rozen R: Homocysteine-betaine interactions in a murine model of 5,10-methylenetetrahydrofolate reductase deficiency. FASEB J. 2003 Mar;17(3):512-4. Epub 2003 Jan 22. [PubMed:12551843 ]
  6. Abdelmalek MF, Angulo P, Jorgensen RA, Sylvestre PB, Lindor KD: Betaine, a promising new agent for patients with nonalcoholic steatohepatitis: results of a pilot study. Am J Gastroenterol. 2001 Sep;96(9):2711-7. [PubMed:11569700 ]
  7. Abu Al-Soud W, Radstrom P: Effects of amplification facilitators on diagnostic PCR in the presence of blood, feces, and meat. J Clin Microbiol. 2000 Dec;38(12):4463-70. [PubMed:11101581 ]
  8. Sakamoto A, Ono H, Mizoguchi N, Sakura N: Betaine and homocysteine concentrations in infant formulae and breast milk. Pediatr Int. 2001 Dec;43(6):637-40. [PubMed:11737741 ]
  9. Schwab U, Torronen A, Toppinen L, Alfthan G, Saarinen M, Aro A, Uusitupa M: Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects. Am J Clin Nutr. 2002 Nov;76(5):961-7. [PubMed:12399266 ]
  10. Chambers ST, Kunin CM: Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731-7. [PubMed:3546377 ]
  11. Laryea MD, Steinhagen F, Pawliczek S, Wendel U: Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine. Clin Chem. 1998 Sep;44(9):1937-41. [PubMed:9732980 ]
  12. Chung YL, Rider LG, Bell JD, Summers RM, Zemel LS, Rennebohm RM, Passo MH, Hicks J, Miller FW, Scott DL: Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies. Arthritis Rheum. 2005 Aug 15;53(4):565-70. [PubMed:16082628 ]
  13. Go EK, Jung KJ, Kim JY, Yu BP, Chung HY: Betaine suppresses proinflammatory signaling during aging: the involvement of nuclear factor-kappaB via nuclear factor-inducing kinase/IkappaB kinase and mitogen-activated protein kinases. J Gerontol A Biol Sci Med Sci. 2005 Oct;60(10):1252-64. [PubMed:16282556 ]
  14. Lever M, Slow S: The clinical significance of betaine, an osmolyte with a key role in methyl group metabolism. Clin Biochem. 2010 Jun;43(9):732-44. doi: 10.1016/j.clinbiochem.2010.03.009. Epub 2010 Mar 25. [PubMed:20346934 ]
  15. Amiraslani B, Sabouni F, Abbasi S, Nazem H, Sabet M: Recognition of betaine as an inhibitor of lipopolysaccharide-induced nitric oxide production in activated microglial cells. Iran Biomed J. 2012;16(2):84-9. [PubMed:22801281 ]
  16. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
  17. Chen X, Gu M, Li T, Sun Y: Metabolite reanalysis revealed potential biomarkers for COVID-19: a potential link with immune response. Future Microbiol. 2021 May;16:577-588. doi: 10.2217/fmb-2021-0047. Epub 2021 May 11. [PubMed:33973485 ]