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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015472

Secondary Accession Numbers

HMDB15472

Metabolite Identification

Common Name

Neostigmine

Description

Neostigmine is only found in individuals that have used or taken this drug. It is a cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier. [PubChem]Neostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. The drug inhibits acetylcholinesterase which is responsible for the degredation of acetylcholine. So, with acetylcholinesterase inhibited, more acetylcholine is present By interfering with the breakdown of acetylcholine, neostigmine indirectly stimulates both nicotinic and muscarinic receptors which are involved in muscle contraction. It does not cross the blood-brain barrier.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015472
     RDKit          3D
Neostigmine
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6104   -0.7720   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.3654    0.6580 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8651   -0.4785    1.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.1397    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    0.5178    1.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692    0.2415   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689    0.7279   -0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836    2.0714   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    2.5816   -0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    1.7260   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    0.3768   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8512   -0.4606   -0.1782 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6138   -1.4766    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0056    0.3188    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454   -1.0608   -1.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235   -0.1097   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0098    0.1340   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3844   -1.5598   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -1.2025   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0374   -1.5200    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660   -0.0425    1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    0.1425    2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452    2.7310   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    3.6462   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294    2.1714   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -1.7509    1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -2.3999    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246   -1.0721    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.0956    0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4745    0.8436   -0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065   -0.3814    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316   -1.1132   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -0.4239   -2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7261   -2.0958   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -1.1799   -0.1867 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  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  1  12   1
M  END

1400
  Mrv0541 02231215282D          

 16 16  0  0  0  0            999 V2000
   19.1051  -10.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8217   -9.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1086  -11.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921   -9.8782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5348  -10.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8217  -11.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6789  -10.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5348  -11.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2514   -9.8748    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.9623   -9.8816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6789  -11.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2317   -9.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8605   -9.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7348  -10.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2526  -10.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9623   -9.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
  6  8  1  0  0  0  0
M  CHG  1   9   1
M  END
> <DATABASE_ID>
HMDB0015472

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1

> <INCHI_KEY>
ALWKGYPQUAPLQC-UHFFFAOYSA-N

> <FORMULA>
C12H19N2O2

> <MOLECULAR_WEIGHT>
223.2915

> <EXACT_MASS>
223.144652862

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.084923818080448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-2.2459823888050785

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
75.2818

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neostigmine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015472
     RDKit          3D
Neostigmine
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6104   -0.7720   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.3654    0.6580 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8651   -0.4785    1.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.1397    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    0.5178    1.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692    0.2415   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689    0.7279   -0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836    2.0714   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    2.5816   -0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    1.7260   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    0.3768   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8512   -0.4606   -0.1782 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6138   -1.4766    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0056    0.3188    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454   -1.0608   -1.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235   -0.1097   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0098    0.1340   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3844   -1.5598   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -1.2025   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0374   -1.5200    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660   -0.0425    1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    0.1425    2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452    2.7310   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    3.6462   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294    2.1714   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -1.7509    1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -2.3999    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246   -1.0721    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.0956    0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4745    0.8436   -0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065   -0.3814    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316   -1.1132   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -0.4239   -2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7261   -2.0958   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -1.1799   -0.1867 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  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  1  12   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1400                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      35.663 -19.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      37.001 -18.433   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.669 -20.750   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      34.332 -18.439   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      38.332 -19.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.001 -21.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.001 -19.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.332 -20.743   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      39.669 -18.433   0.000  0.00  0.00           N+1
HETATM   10  N   UNK     0      31.663 -18.446   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      33.001 -20.756   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      41.499 -17.422   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.940 -17.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.572 -19.758   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.338 -19.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.663 -16.903   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    3    8                                                       
CONECT    7    4   10   11                                                  
CONECT    8    5    6                                                       
CONECT    9    5   12   13   14                                             
CONECT   10    7   15   16                                                  
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0015472
HETATM    1  C1  UNL     1       4.610  -0.772  -0.620  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.067  -0.365   0.658  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.865  -0.478   1.839  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.726   0.140   0.668  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.172   0.518   1.741  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.969   0.241  -0.486  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.669   0.728  -0.499  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.384   2.071  -0.677  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.874   2.582  -0.696  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.944   1.726  -0.528  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.718   0.377  -0.346  1.00  0.00           C  
HETATM   12  N2  UNL     1      -2.851  -0.461  -0.178  1.00  0.00           N1+
HETATM   13  C9  UNL     1      -2.614  -1.477   0.831  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.006   0.319   0.211  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.145  -1.061  -1.473  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.423  -0.110  -0.333  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.010   0.134  -1.154  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.384  -1.560  -0.527  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.793  -1.202  -1.248  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.037  -1.520   2.164  1.00  0.00           H  
HETATM   21  H5  UNL     1       5.866  -0.042   1.640  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.396   0.143   2.628  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.245   2.731  -0.808  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.990   3.646  -0.842  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.929   2.171  -0.549  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.588  -1.751   1.320  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.184  -2.400   0.434  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.925  -1.072   1.608  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.777   1.096   0.963  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.474   0.844  -0.656  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.806  -0.381   0.581  1.00  0.00           H  
HETATM   32  H16 UNL     1      -4.232  -1.113  -1.676  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.709  -0.424  -2.280  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.726  -2.096  -1.517  1.00  0.00           H  
HETATM   35  H19 UNL     1      -0.278  -1.180  -0.187  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    8   16
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   16   16
CONECT   12   13   14   15
CONECT   13   26   27   28
CONECT   14   29   30   31
CONECT   15   32   33   34
CONECT   16   35
END

HMDB0015472
     RDKit          3D
Neostigmine
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6104   -0.7720   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.3654    0.6580 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8651   -0.4785    1.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.1397    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    0.5178    1.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692    0.2415   -0.4855 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689    0.7279   -0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836    2.0714   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    2.5816   -0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442    1.7260   -0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    0.3768   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8512   -0.4606   -0.1782 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6138   -1.4766    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0056    0.3188    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1454   -1.0608   -1.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235   -0.1097   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0098    0.1340   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3844   -1.5598   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -1.2025   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0374   -1.5200    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660   -0.0425    1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    0.1425    2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452    2.7310   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900    3.6462   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294    2.1714   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -1.7509    1.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -2.3999    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246   -1.0721    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.0956    0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4745    0.8436   -0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065   -0.3814    0.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316   -1.1132   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -0.4239   -2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7261   -2.0958   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -1.1799   -0.1867 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  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  1  12   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(m-Hydroxyphenyl)trimethylammonium dimethylcarbamate	ChEBI
3-Trimethylammoniumphenyl N,N-dimethylcarbamate	ChEBI
Eustigmin	ChEBI
Eustigmine	ChEBI
m-Trimethylammoniumphenyldimethylcarbamate	ChEBI
Prostigmine	ChEBI
Vagostigmine	ChEBI
Prostigmin	Kegg
(m-Hydroxyphenyl)trimethylammonium dimethylcarbamic acid	Generator
3-Trimethylammoniumphenyl N,N-dimethylcarbamic acid	Generator
m-Trimethylammoniumphenyldimethylcarbamic acid	Generator
Proserine	HMDB
Neostigmine bromide	HMDB
Methylsulfate, neostigmine	HMDB
Polstigmine	HMDB
Syntostigmine	HMDB
Bromide, neostigmine	HMDB
Neostigmine methylsulfate	HMDB
Prozerin	HMDB
Synstigmin	HMDB

Chemical Formula

C₁₂H₁₉N₂O₂

Average Molecular Weight

223.2915

Monoisotopic Molecular Weight

223.144652862

IUPAC Name

3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium

Traditional Name

neostigmine

CAS Registry Number

59-99-4

SMILES

CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C

InChI Identifier

InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1

InChI Key

ALWKGYPQUAPLQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxy compounds

Direct Parent

Phenoxy compounds

Alternative Parents

Substituents

Phenoxy compound
Aniline or substituted anilines
Quaternary ammonium salt
Carbamic acid ester
Carbonic acid derivative
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic salt
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:7514 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015472)
Membrane (HMDB: HMDB0015472)

Source

Exogenous

Exogenous (HMDB: HMDB0015472)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.068 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.2	ChemAxon
logS	-3.6	ALOGPS
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.28 m³·mol⁻¹	ChemAxon
Polarizability	25.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	155.11	30932474
DeepCCS	[M-H]-	152.714	30932474
DeepCCS	[M-2H]-	185.761	30932474
DeepCCS	[M+Na]+	161.023	30932474
AllCCS	[M+H]+	150.7	32859911
AllCCS	[M+H-H2O]+	147.1	32859911
AllCCS	[M+NH4]+	154.0	32859911
AllCCS	[M+Na]+	154.9	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.91 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8303 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1947.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	292.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	106.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	437.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	511.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1228.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	336.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1405.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neostigmine	CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C	2163.6	Standard polar	33892256
Neostigmine	CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C	1385.0	Standard non polar	33892256
Neostigmine	CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C	1663.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Neostigmine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9720000000-c12a62c0ea57c3a5c3c0	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neostigmine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neostigmine LC-ESI-QQ , positive-QTOF	splash10-00di-0090000000-7feec7180feed2165741	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neostigmine LC-ESI-QQ , positive-QTOF	splash10-00di-0090000000-33ad4a0e0807f82bab39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neostigmine LC-ESI-QQ , positive-QTOF	splash10-0ab9-2090000000-285ee2bce4f4c2097510	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neostigmine LC-ESI-QQ , positive-QTOF	splash10-00di-9110000000-a2386202e9dc8c7c753f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neostigmine LC-ESI-QQ , positive-QTOF	splash10-00di-9100000000-b80120a3f55bb762fe51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neostigmine LC-ESI-IT , positive-QTOF	splash10-0a4i-0090000000-675c3ee4663579ce2125	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neostigmine 10V, Positive-QTOF	splash10-00di-3290000000-b986a6e34fcfb8d59d47	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neostigmine 20V, Positive-QTOF	splash10-00dr-5920000000-f27e9d56f2a899526aed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neostigmine 40V, Positive-QTOF	splash10-00di-9400000000-a34da59427598585aa1e	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01400	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01400	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01400

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4301

KEGG Compound ID

C07258

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Neostigmine

METLIN ID

Not Available

PubChem Compound

4456

PDB ID

Not Available

ChEBI ID

7514

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetylcholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:: ACHE
Uniprot ID:: P22303
Molecular weight:: 67795.525

References

Trevisani GT, Hyman NH, Church JM: Neostigmine: safe and effective treatment for acute colonic pseudo-obstruction. Dis Colon Rectum. 2000 May;43(5):599-603. [PubMed:10826417 ]
Naves LA, Van der Kloot W: Repetitive nerve stimulation decreases the acetylcholine content of quanta at the frog neuromuscular junction. J Physiol. 2001 May 1;532(Pt 3):637-47. [PubMed:11313435 ]
Takeuchi K, Kawauchi S, Araki H, Ueki S, Furukawa O: Stimulation by nizatidine, a histamine H(2)-receptor antagonist, of duodenal HCO(3)(-)secretion in rats:relation to anti-cholinesterase activity. World J Gastroenterol. 2000 Oct;6(5):651-658. [PubMed:11819669 ]
Minic J, Chatonnet A, Krejci E, Molgo J: Butyrylcholinesterase and acetylcholinesterase activity and quantal transmitter release at normal and acetylcholinesterase knockout mouse neuromuscular junctions. Br J Pharmacol. 2003 Jan;138(1):177-87. [PubMed:12522088 ]
Beck KD, Brennan FX, Moldow RL, Ottenweller JE, Zhu G, Servatius RJ: Stress interacts with peripheral cholinesterase inhibitors to cause central nervous system effects. Life Sci. 2003 May 23;73(1):41-51. [PubMed:12726885 ]
Zhang B, Hepner DL, Tran MH, Friedman M, Korn JR, Menzin J: Neuromuscular blockade, reversal agent use, and operating room time: retrospective analysis of US inpatient surgeries. Curr Med Res Opin. 2009 Apr;25(4):943-50. doi: 10.1185/03007990902769054 . [PubMed:19257799 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Saito S: Cholinesterase inhibitors induce growth cone collapse and inhibit neurite extension in primary cultured chick neurons. Neurotoxicol Teratol. 1998 Jul-Aug;20(4):411-9. [PubMed:9697967 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

Showing metabocard for Neostigmine (HMDB0015472)

MOL for HMDB0015472 (Neostigmine)

3D MOL for HMDB0015472 (Neostigmine)

3D SDF for HMDB0015472 (Neostigmine)

3D-SDF for HMDB0015472 (Neostigmine)

PDB for HMDB0015472 (Neostigmine)

3D PDB for HMDB0015472 (Neostigmine)

SMILES for HMDB0015472 (Neostigmine)

INCHI for HMDB0015472 (Neostigmine)

Structure for HMDB0015472 (Neostigmine)

3D Structure for HMDB0015472 (Neostigmine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

Transporters

References