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Showing NP-Card for 1,1-Dimethylbiguanide (NP0000883)

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Record Information
Version1.0
Created at2006-05-18 08:29:34 UTC
Updated at2021-06-29 00:47:17 UTC
NP-MRD IDNP0000883
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,1-Dimethylbiguanide
Description1,1-Dimethylbiguanide, commonly known as metformin, is a member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1. It has a role as a hypoglycemic agent, a xenobiotic and an environmental contaminant. It derives from a biguanide. It is a conjugate base of a metformin(1+). Metformin is a biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. Metformin is the most popular anti-diabetic drug in the United States and one of the most prescribed drugs in the country overall, with nearly 35 million prescriptions filled in 2006 for generic metformin alone. It is also used in the treatment of polycystic ovary syndrome. It is not associated with weight gain and is taken by mouth. It is sometimes used as an off-label augment to attenuate the risk of weight gain in people who take antipsychotics as well as phenelzine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000883 (1,1-Dimethylbiguanide)


  Mrv1652305261923512D          

  9  8  0  0  0  0            999 V2000
   -3.1875    1.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    1.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    2.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3849    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  2  2  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  5  2  0  0  0  0
  6  8  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for NP0000883 (1,1-Dimethylbiguanide)

HMDB0001921
     RDKit          3D
1,1-Dimethylbiguanide
 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.9652   -1.0562    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153   -0.0724   -0.0484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5783    0.4386   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.3675   -0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    0.1960   -2.1821 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.9883   -0.4397 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    0.2893    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3888    0.7624    1.4579 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969   -0.9629   -0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046   -1.7762    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986   -1.6577    1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.5333    1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400    1.1348    0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    0.9775   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838   -0.4245   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.4827   -2.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357    1.9996   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0754    1.6679    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -1.8305    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061   -0.9911   -0.8171 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  2  3
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0000883 (1,1-Dimethylbiguanide)


  Mrv1652305261923512D          

  9  8  0  0  0  0            999 V2000
   -3.1875    1.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7586    1.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    2.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296    1.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3849    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  2  2  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  5  2  0  0  0  0
  6  8  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000883

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)C(=N)NC(N)=N

> <INCHI_IDENTIFIER>
InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)

> <INCHI_KEY>
XZWYZXLIPXDOLR-UHFFFAOYSA-N

> <FORMULA>
C4H11N5

> <MOLECULAR_WEIGHT>
129.1636

> <EXACT_MASS>
129.101445377

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.427402057500638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-carbamimidamido-N,N-dimethylmethanimidamide

> <ALOGPS_LOGP>
-1.83

> <JCHEM_LOGP>
-0.9184292649999999

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
12.325150598103365

> <JCHEM_POLAR_SURFACE_AREA>
88.99

> <JCHEM_REFRACTIVITY>
56.642700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metformin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000883 (1,1-Dimethylbiguanide)

HMDB0001921
     RDKit          3D
1,1-Dimethylbiguanide
 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.9652   -1.0562    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153   -0.0724   -0.0484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5783    0.4386   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.3675   -0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    0.1960   -2.1821 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.9883   -0.4397 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    0.2893    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3888    0.7624    1.4579 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969   -0.9629   -0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046   -1.7762    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986   -1.6577    1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.5333    1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8400    1.1348    0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    0.9775   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838   -0.4245   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.4827   -2.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357    1.9996   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0754    1.6679    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -1.8305    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061   -0.9911   -0.8171 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  2  3
  4  6  1  0
  6  7  1  0
  7  8  2  3
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
M  END
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PDB for NP0000883 (1,1-Dimethylbiguanide)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  N   UNK     0      -5.950   2.508   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      -4.616   0.198   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -4.616   1.738   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -3.283   2.508   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      -1.949   0.198   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.949   1.738   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.615   4.048   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.615   2.508   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.718   1.738   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    3                                                            
CONECT    3    1    2    4                                                  
CONECT    4    3    6                                                       
CONECT    5    6                                                            
CONECT    6    4    5    8                                                  
CONECT    7    8                                                            
CONECT    8    6    7    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000883 (1,1-Dimethylbiguanide)

COMPND    HMDB0001921
HETATM    1  C1  UNL     1      -0.965  -1.056   0.988  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.215  -0.072  -0.048  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.578   0.439  -0.156  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.179   0.367  -0.914  1.00  0.00           C  
HETATM    5  N2  UNL     1      -0.319   0.196  -2.182  1.00  0.00           N  
HETATM    6  N3  UNL     1       1.006   0.988  -0.440  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.967   0.289   0.345  1.00  0.00           C  
HETATM    8  N4  UNL     1       2.389   0.762   1.458  1.00  0.00           N  
HETATM    9  N5  UNL     1       2.497  -0.963  -0.076  1.00  0.00           N  
HETATM   10  H1  UNL     1      -0.205  -1.776   0.686  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.899  -1.658   1.198  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.732  -0.533   1.936  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.840   1.135   0.635  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.713   0.977  -1.128  1.00  0.00           H  
HETATM   15  H6  UNL     1      -3.284  -0.425  -0.178  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.380   0.483  -2.890  1.00  0.00           H  
HETATM   17  H8  UNL     1       1.236   2.000  -0.645  1.00  0.00           H  
HETATM   18  H9  UNL     1       2.075   1.668   1.869  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.173  -1.830   0.357  1.00  0.00           H  
HETATM   20  H11 UNL     1       3.206  -0.991  -0.817  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4
CONECT    3   13   14   15
CONECT    4    5    5    6
CONECT    5   16
CONECT    6    7   17
CONECT    7    8    8    9
CONECT    8   18
CONECT    9   19   20
END
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SMILES for NP0000883 (1,1-Dimethylbiguanide)

CN(C)C(=N)NC(N)=N
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INCHI for NP0000883 (1,1-Dimethylbiguanide)

InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
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View in JSmol
Synonyms
ValueSource
DimethylbiguanideChEBI
DimethyldiguanideChEBI
LA 6023ChEBI
LA-6023ChEBI
MetforminaChEBI
MetformineChEBI
MetforminumChEBI
N,N-DimethylbiguanideChEBI
N,N-DimethyldiguanideChEBI
N,N-DimethylguanylguanidineChEBI
N,N-Dimethylimidodicarbonimidic diamideChEBI
N(1),N(1)-DimethylbiguanideChEBI
1,1-Dimethyl biguanideHMDB
DiabefagosHMDB
DiabexHMDB
DiaforminHMDB
DianbenHMDB
DMBGHMDB
FortametHMDB
GlucophageHMDB
GlumetzaHMDB
MeguanHMDB
MetforminHMDB
MetiguanideHMDB
N1,N1-DimethylbiguanideHMDB
ObimetHMDB
RiometHMDB
DimethylbiguanidineHMDB
DimethylguanylguanidineHMDB
Metformin HCLHMDB
HCL, MetforminHMDB
Hydrochloride, metforminHMDB
Metformin hydrochlorideHMDB
1,1-DimethylbiguanideChEBI
Chemical FormulaC4H11N5
Average Mass129.1636 Da
Monoisotopic Mass129.10145 Da
IUPAC Name1-carbamimidamido-N,N-dimethylmethanimidamide
Traditional Namemetformin
CAS Registry Number1115-70-4
SMILES
CN(C)C(=N)NC(N)=N
InChI Identifier
InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
InChI KeyXZWYZXLIPXDOLR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)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
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biguanides. These are organic compounds containing two N-linked guanidines.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentBiguanides
Alternative Parents
Substituents
  • Biguanide
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point223 - 226 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP-1.8ALOGPS
logP-0.92ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)12.33ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area88.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.64 m³·mol⁻¹ChemAxon
Polarizability13.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001921
DrugBank IDDB00331
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022739
KNApSAcK IDNot Available
Chemspider ID3949
KEGG Compound IDC07151
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetformin
METLIN ID6390
PubChem Compound4091
PDB IDNot Available
ChEBI ID6801
Good Scents IDNot Available
References
General References
  1. Musi N, Hirshman MF, Nygren J, Svanfeldt M, Bavenholm P, Rooyackers O, Zhou G, Williamson JM, Ljunqvist O, Efendic S, Moller DE, Thorell A, Goodyear LJ: Metformin increases AMP-activated protein kinase activity in skeletal muscle of subjects with type 2 diabetes. Diabetes. 2002 Jul;51(7):2074-81. [PubMed:12086935 ]
  2. Bridger T, MacDonald S, Baltzer F, Rodd C: Randomized placebo-controlled trial of metformin for adolescents with polycystic ovary syndrome. Arch Pediatr Adolesc Med. 2006 Mar;160(3):241-6. [PubMed:16520442 ]
  3. Seale FG 4th, Robinson RD, Neal GS: Association of metformin and pregnancy in the polycystic ovary syndrome. A report of three cases. J Reprod Med. 2000 Jun;45(6):507-10. [PubMed:10900588 ]
  4. Briggs GG, Ambrose PJ, Nageotte MP, Padilla G, Wan S: Excretion of metformin into breast milk and the effect on nursing infants. Obstet Gynecol. 2005 Jun;105(6):1437-41. [PubMed:15932841 ]
  5. De Jager J, Kooy A, Lehert P, Bets D, Wulffele MG, Teerlink T, Scheffer PG, Schalkwijk CG, Donker AJ, Stehouwer CD: Effects of short-term treatment with metformin on markers of endothelial function and inflammatory activity in type 2 diabetes mellitus: a randomized, placebo-controlled trial. J Intern Med. 2005 Jan;257(1):100-9. [PubMed:15606381 ]
  6. Mughal MA, Jan M, Maheri WM, Memon MY, Ali M: The effect of metformin on glycemic control, serum lipids and lipoproteins in diet alone and sulfonylurea-treated type 2 diabetic patients with sub-optimal metabolic control. J Pak Med Assoc. 2000 Nov;50(11):381-6. [PubMed:11126815 ]
  7. Einhorn D, Rendell M, Rosenzweig J, Egan JW, Mathisen AL, Schneider RL: Pioglitazone hydrochloride in combination with metformin in the treatment of type 2 diabetes mellitus: a randomized, placebo-controlled study. The Pioglitazone 027 Study Group. Clin Ther. 2000 Dec;22(12):1395-409. [PubMed:11192132 ]
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