NP-MRD: Showing NP-Card for Neostigmine (NP0002901)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-11-23 19:43:11 UTC

Updated at

2021-08-19 23:59:31 UTC

NP-MRD ID

NP0002901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neostigmine

Provided By

BMRB

Description

Neostigmine, also known as proserine or synstigmin, belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. Neostigmine was first documented in 1982 (PMID: 7200780). Based on a literature review a small amount of articles have been published on Neostigmine (PMID: 8584207) (PMID: 34601981) (PMID: 34599343).

Structure

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


     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -5.7936    0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5085   -0.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5359   -1.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1960    0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1685    1.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9108   -0.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709    1.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267    1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844   -0.4382    0.0000 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.0581    0.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108   -1.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -0.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5672   -0.8073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200    1.7629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0787    1.2514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0356   -1.7681    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0361   -1.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -3.2953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8560    2.6562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7690    4.1085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018    2.2639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669    0.4860    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323    1.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    2.1320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083   -2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -1.2837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -3.0084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -2.0207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1155   -0.5143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8547   -1.9854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594   -1.8905    0.0000 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
 12 11  1  6
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  1
  1 18  1  0
  1 19  1  0
  3 20  1  6
  3 21  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  1
 13 27  1  0
 13 28  1  0
 14 29  1  6
 14 30  1  0
 14 31  1  0
 15 32  1  1
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  1  12   1
M  END

NP0002901
     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    4.4337    0.6736    1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -0.2004    0.2278 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230   -1.1471   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446   -0.0872   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089   -0.8463   -1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454    0.8175    0.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544    0.9825   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3081    1.8724   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    2.0625   -1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    1.3562   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.4572   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -0.2938    0.2676 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1136   -0.1144   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112   -1.7264    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.0196    1.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189    0.2741    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344    0.4203    2.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    1.7337    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    0.4717    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -1.7613    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8919   -0.5818   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6418   -1.8064   -1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.4348   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    2.7611   -2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553    1.4793   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -0.2600   -1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723   -0.8254    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115    0.9049   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094   -1.9768   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2681   -2.3245    0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.9652    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -0.1495    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.5624    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6913    1.1083    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -0.4148    0.9976 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


     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -5.7936    0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5085   -0.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5359   -1.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1960    0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1685    1.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9108   -0.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709    1.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267    1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844   -0.4382    0.0000 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.0581    0.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108   -1.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -0.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5672   -0.8073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200    1.7629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0787    1.2514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0356   -1.7681    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0361   -1.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -3.2953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8560    2.6562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7690    4.1085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018    2.2639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669    0.4860    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323    1.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    2.1320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083   -2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -1.2837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -3.0084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -2.0207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1155   -0.5143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8547   -1.9854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594   -1.8905    0.0000 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
 12 11  1  6
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  1
  1 18  1  0
  1 19  1  0
  3 20  1  6
  3 21  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  1
 13 27  1  0
 13 28  1  0
 14 29  1  6
 14 30  1  0
 14 31  1  0
 15 32  1  1
 15 33  1  0
 15 34  1  0
 16 35  1  0
M  CHG  1  12   1
M  END
> <DATABASE_ID>
NP0002901

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0002901
     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    4.4337    0.6736    1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -0.2004    0.2278 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230   -1.1471   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446   -0.0872   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089   -0.8463   -1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454    0.8175    0.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544    0.9825   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3081    1.8724   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    2.0625   -1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    1.3562   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.4572   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -0.2938    0.2676 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1136   -0.1144   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112   -1.7264    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.0196    1.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189    0.2741    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344    0.4203    2.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    1.7337    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    0.4717    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -1.7613    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8919   -0.5818   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6418   -1.8064   -1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.4348   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    2.7611   -2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553    1.4793   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -0.2600   -1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723   -0.8254    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115    0.9049   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094   -1.9768   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2681   -2.3245    0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.9652    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -0.1495    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.5624    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6913    1.1083    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -0.4148    0.9976 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    NP0002901
HETATM    1  C1  UNL     1       4.434   0.674   1.328  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.047  -0.200   0.228  1.00  0.00           N  
HETATM    3  C2  UNL     1       5.023  -1.147  -0.257  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.745  -0.087  -0.314  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.409  -0.846  -1.269  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.845   0.818   0.167  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.554   0.982  -0.316  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.308   1.872  -1.338  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.977   2.062  -1.846  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.047   1.356  -1.334  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.801   0.457  -0.303  1.00  0.00           C  
HETATM   12  N2  UNL     1      -2.828  -0.294   0.268  1.00  0.00           N1+
HETATM   13  C9  UNL     1      -4.114  -0.114  -0.359  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.511  -1.726   0.141  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.956   0.020   1.675  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.519   0.274   0.197  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.734   0.420   2.174  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.320   1.734   1.022  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.471   0.472   1.662  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.474  -1.761   0.552  1.00  0.00           H  
HETATM   21  H5  UNL     1       5.892  -0.582  -0.703  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.642  -1.806  -1.034  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.113   2.435  -1.756  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.175   2.761  -2.649  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.055   1.479  -1.705  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.088  -0.260  -1.455  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.872  -0.825   0.027  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.511   0.905  -0.175  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.609  -1.977  -0.937  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.268  -2.324   0.712  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.504  -1.965   0.472  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.977  -0.149   2.066  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.217  -0.562   2.284  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.691   1.108   1.778  1.00  0.00           H  
HETATM   35  H19 UNL     1      -0.289  -0.415   0.998  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

NP0002901
     RDKit          3D

35 35  0  0  0  0  0  0  0  0999 V2000
    4.4337    0.6736    1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -0.2004    0.2278 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230   -1.1471   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446   -0.0872   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089   -0.8463   -1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454    0.8175    0.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544    0.9825   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3081    1.8724   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    2.0625   -1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    1.3562   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.4572   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -0.2938    0.2676 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1136   -0.1144   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112   -1.7264    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.0196    1.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189    0.2741    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344    0.4203    2.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    1.7337    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    0.4717    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4739   -1.7613    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8919   -0.5818   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6418   -1.8064   -1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    2.4348   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    2.7611   -2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553    1.4793   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -0.2600   -1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8723   -0.8254    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115    0.9049   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094   -1.9768   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2681   -2.3245    0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.9652    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -0.1495    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.5624    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6913    1.1083    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -0.4148    0.9976 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

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 Mass

223.2915 Da

Monoisotopic Mass

223.14465 Da

IUPAC Name

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

Traditional Name

neostigmine

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	296.00 to 298.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.24 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.523 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015472

DrugBank ID

DB01400

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1020451

References

General References

Sobek V: The effect of calcium, neostigmine and 4-aminopyridine upon respiratory arrest and depression of cardiovascular functions after aminoglycosidic antibiotics. Arzneimittelforschung. 1982;32(3):222-4. [PubMed:7200780 ]
Shen E, Sun X: Endogenous acetylcholine-induced Fos expression in magnocellular neurosecretory neurons in the supraoptic nucleus of the rat hypothalamus. Neurosci Lett. 1995 Aug 11;195(3):191-4. doi: 10.1016/0304-3940(95)11816-f. [PubMed:8584207 ]
Hile GB, Healy KJ, Almassalkhi LR: Rocuronium Reversal in the Emergency Department: Retrospective Evaluation of Hemodynamic Instability Following Administration of Sugammadex Versus Neostigmine With Glycopyrrolate. J Pharm Pract. 2021 Oct 2:8971900211048747. doi: 10.1177/08971900211048747. [PubMed:34601981 ]
Deng J, Balouch M, Albrink M, Camporesi EM: Sugammadex Reduces PACU Recovery Time after Abdominal Surgery Compared with Neostigmine. South Med J. 2021 Oct;114(10):644-648. doi: 10.14423/SMJ.0000000000001304. [PubMed:34599343 ]

Showing NP-Card for Neostigmine (NP0002901)

MOL for NP0002901 (Neostigmine)

3D MOL for NP0002901 (Neostigmine)

3D SDF for NP0002901 (Neostigmine)

3D-SDF for NP0002901 (Neostigmine)

PDB for NP0002901 (Neostigmine)

3D PDB for NP0002901 (Neostigmine)

SMILES for NP0002901 (Neostigmine)

INCHI for NP0002901 (Neostigmine)

Structure for NP0002901 (Neostigmine)

3D Structure for NP0002901 (Neostigmine)