Showing NP-Card for Dimethylglycine (NP0000814)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:40:59 UTC
NP-MRD IDNP0000814
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethylglycine
DescriptionDimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into Glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N, N-dimethylglycine by betaine-homocysteine methyltransferase. Dimethylglycine in the urine is a biomarker for the consumption of legumes.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000814 (Dimethylglycine)

  Mrv1652306051920022D          

  7  6  0  0  0  0            999 V2000
   -1.6069   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924   -0.7473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    0.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358   -1.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for NP0000814 (Dimethylglycine)

HMDB0000092
     RDKit          3D
Dimethylglycine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.7842    0.6357   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    0.0011    0.4783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7991   -1.4137    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245    0.5872   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142    0.2420    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399   -0.5887    1.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400    0.9123    0.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    0.0041   -0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    0.7445   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388    1.6661    0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054   -1.7686    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811   -2.0087    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0968   -1.4503   -0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575    0.2699   -1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    1.6896   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8389    0.4776   -0.1164 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
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3D SDF for NP0000814 (Dimethylglycine)

  Mrv1652306051920022D          

  7  6  0  0  0  0            999 V2000
   -1.6069   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924   -0.7473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    0.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214   -0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358   -1.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
FFDGPVCHZBVARC-UHFFFAOYSA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.470047738620533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(dimethylamino)acetic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-3.0607825071662678

> <ALOGPS_LOGS>
0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8808127451470078

> <JCHEM_PKA_STRONGEST_BASIC>
9.691600277978429

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
26.0727

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.39e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000814 (Dimethylglycine)

HMDB0000092
     RDKit          3D
Dimethylglycine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.7842    0.6357   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    0.0011    0.4783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7991   -1.4137    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245    0.5872   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142    0.2420    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399   -0.5887    1.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400    0.9123    0.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    0.0041   -0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880    0.7445   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388    1.6661    0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054   -1.7686    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811   -2.0087    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0968   -1.4503   -0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575    0.2699   -1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    1.6896   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8389    0.4776   -0.1164 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
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PDB for NP0000814 (Dimethylglycine)

HEADER    PROTEIN                                 05-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.000  -2.165   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.666  -1.395   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.332  -2.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.666   0.145   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.333  -1.395   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.333   0.145   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -5.667  -2.165   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0000814 (Dimethylglycine)

COMPND    HMDB0000092
HETATM    1  C1  UNL     1      -1.784   0.636  -0.201  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.635   0.001   0.478  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.799  -1.414   0.122  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.524   0.587  -0.137  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.814   0.242   0.515  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.940  -0.589   1.429  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.940   0.912   0.053  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.685   0.004  -0.157  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.488   0.745  -1.257  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.939   1.666   0.187  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.705  -1.769   0.691  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.081  -2.009   0.346  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.097  -1.450  -0.940  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.558   0.270  -1.230  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.436   1.690  -0.158  1.00  0.00           H  
HETATM   16  H9  UNL     1       3.839   0.478  -0.116  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4
CONECT    3   11   12   13
CONECT    4    5   14   15
CONECT    5    6    6    7
CONECT    7   16
END
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SMILES for NP0000814 (Dimethylglycine)

CN(C)CC(O)=O
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INCHI for NP0000814 (Dimethylglycine)

InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
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Synonyms
ValueSource
(Dimethylamino)acetic acidChEBI
2-(Dimethylamino)acetic acidChEBI
N,N-Dimethylaminoacetic acidChEBI
N-MethylsarcosineChEBI
(Dimethylamino)acetateGenerator
2-(Dimethylamino)acetateGenerator
N,N-DimethylaminoacetateGenerator
N,N-DimethylglycineHMDB
N-Methylsarcosine N,N-dimethyl-glycineHMDB
Dimethylglycine, monopotassium saltHMDB
Dimethylglycine, sodium saltHMDB
Dimethylglycine, calcium saltHMDB
Dimethylglycine monohydrochlorideHMDB
2-(N,N-Dimethylamino)acetic acidHMDB
DMGHMDB
DimethylglycineHMDB
Chemical FormulaC4H9NO2
Average Mass103.1198 Da
Monoisotopic Mass103.06333 Da
IUPAC Name2-(dimethylamino)acetic acid
Traditional Namedimethylglycine
CAS Registry Number1118-68-9
SMILES
CN(C)CC(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
InChI KeyFFDGPVCHZBVARC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-02View Spectrum
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.91Tsai, R. S., Testa, B., El Tayar, N., & Carrupt, P. A. (1991). Structure-lipophilicity relationships of zwitterionic amino acids. Journal of the Chemical Society, Perkin Transactions 2, (11), 1797-1802.
Predicted Properties
PropertyValueSource
Water Solubility939 g/LALOGPS
logP-1.7ALOGPS
logP-3.1ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.07 m³·mol⁻¹ChemAxon
Polarizability10.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000092
DrugBank IDDB02083
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021893
KNApSAcK IDC00052266
Chemspider ID653
KEGG Compound IDC01026
BioCyc IDDIMETHYL-GLYCINE
BiGG ID36652
Wikipedia LinkDimethylglycine
METLIN ID277
PubChem Compound673
PDB IDNot Available
ChEBI ID17724
Good Scents IDNot Available
References
General References