Np mrd loader

Showing NP-Card for N,N-Dimethylglycine (NP0331777)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2023-08-23 16:02:05 UTC
Updated at2024-09-03 04:16:53 UTC
NP-MRD IDNP0331777
Natural Product DOIhttps://doi.org/10.57994/0844
Secondary Accession NumbersNone
Natural Product Identification
Common NameN,N-Dimethylglycine
DescriptionDimethylglycine, also known as N-methylsarcosine or DMG, 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). Dimethylglycine exists in all living organisms, ranging from bacteria to humans. In humans, dimethylglycine is involved in the sarcosine oncometabolite pathway. Dimethylglycine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2021 (PMID: 34491083). Based on a literature review a significant number of articles have been published on Dimethylglycine (PMID: 34392174) (PMID: 34400248) (PMID: 34240265) (PMID: 34224573).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0331777 (N,N-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
Download

3D MOL for NP0331777 (N,N-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
Download

3D SDF for NP0331777 (N,N-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>
NP0331777

> <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

$$$$
Download

3D-SDF for NP0331777 (N,N-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
Download

PDB for NP0331777 (N,N-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
Download

3D PDB for NP0331777 (N,N-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
Download

SMILES for NP0331777 (N,N-Dimethylglycine)

CN(C)CC(O)=O
Download

INCHI for NP0331777 (N,N-Dimethylglycine)

InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
Download
View in JSmol
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 NumberNot Available
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, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2024-05-09View Spectrum
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 NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
Species
Species of OriginNot Available
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
  1. Avraham Y, Mankuta D, Lipsker L, Vorobiev L, Patael S, Hassid G, Berry EM, Albeck A: Beta-Carotene derivatives as novel therapy for the prevention and treatment of autistic symptoms. Bioorg Chem. 2021 Aug 3;115:105224. doi: 10.1016/j.bioorg.2021.105224. [PubMed:34392174 ]
  2. Li L, Zhang W, Zhang S, Song L, Sun Q, Zhang H, Xiang H, Dong X: Bacteria and Archaea Synergistically Convert Glycine Betaine to Biogenic Methane in the Formosa Cold Seep of the South China Sea. mSystems. 2021 Oct 26;6(5):e0070321. doi: 10.1128/mSystems.00703-21. Epub 2021 Sep 7. [PubMed:34491083 ]
  3. Hsieh CP, Chen ST, Lee MY, Huang CM, Chen HH, Chan MH: N, N-dimethylglycine Protects Behavioral Disturbances and Synaptic Deficits Induced by Repeated Ketamine Exposure in Mice. Neuroscience. 2021 Sep 15;472:128-137. doi: 10.1016/j.neuroscience.2021.08.004. Epub 2021 Aug 13. [PubMed:34400248 ]
  4. Gillies NA, Franzke B, Wessner B, Schober-Halper B, Hofmann M, Oesen S, Tosevska A, Strasser EM, Roy NC, Milan AM, Cameron-Smith D, Wagner KH: Nutritional supplementation alters associations between one-carbon metabolites and cardiometabolic risk profiles in older adults: a secondary analysis of the Vienna Active Ageing Study. Eur J Nutr. 2022 Feb;61(1):169-182. doi: 10.1007/s00394-021-02607-y. Epub 2021 Jul 8. [PubMed:34240265 ]
  5. Allaway D, Harrison M, Haydock R, Watson P: Adaptations Supporting Plasma Methionine on a Limited-Methionine, High-Cystine Diet Alter the Canine Plasma Metabolome Consistent with Interventions that Extend Life Span in Other Species. J Nutr. 2021 Oct 1;151(10):3125-3136. doi: 10.1093/jn/nxab204. [PubMed:34224573 ]