NP-MRD: Showing NP-Card for Eserine (NP0050894)

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Record Information

Version

1.0

Created at

2022-04-27 22:22:02 UTC

Updated at

2022-04-27 22:22:02 UTC

NP-MRD ID

NP0050894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eserine

Description

Physostigmine, also known as eserine or antilirium, belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Physostigmine is a drug which is used for the treatment of glaucoma, and in the treatment of severe anticholinergic toxicity. Eserine is found in Chimonanthus fragrans, Physostigma venenosum and Streptomyces albospinus. Physostigmine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    6.5240    0.4282   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052    0.8503    0.3516 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.2536    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -0.6258   -0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.6855    0.9770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8495    0.1120    0.8040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.0162    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102   -1.5794    1.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323   -1.0491    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287    0.0818   -0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353    0.6533   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776    0.4370   -1.1047 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2367    0.1161   -2.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539    1.8539   -0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382    1.6103   -0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    0.3693    0.1398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9966    0.6436    1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -0.4697   -0.6049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9461   -1.4903    0.1735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5423   -2.7361    0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3163    0.0787    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8236    1.2929   -1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2082   -0.3844   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009    1.5756    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -1.4440    2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007   -2.4700    1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    1.5404   -0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.3529   -3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -1.0057   -2.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720    0.6167   -2.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176    2.4957   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689    2.2781   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260    1.4720   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460    2.4647   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1810   -0.1913    2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    0.9319    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.5160    1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -0.8684   -1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1535   -3.2001   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616   -3.5182    0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -2.6618    1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  6
 12 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  6 11  2  0
  9 19  1  0
 19 20  1  0
 12 18  1  0
 11 10  1  0
 19 18  1  0
 18 38  1  6
 17 35  1  0
 17 36  1  0
 17 37  1  0
 15 33  1  0
 15 34  1  0
 14 31  1  0
 14 32  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
  8 26  1  0
  7 25  1  0
  2 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 11 27  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
M  END

981
  Mrv0541 02231215092D          

 21 23  0  0  1  0            999 V2000
    3.5651    0.0678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    1.4644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863   -0.6839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8691    0.5845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2044    0.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4566   -0.6851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1240   -0.2001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7121   -1.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7891   -0.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5322   -1.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7891   -1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5714   -0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3540    1.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3715    0.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    0.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6586    0.1871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1 19  1  0  0  0  0
  2 19  2  0  0  0  0
  3  7  1  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  6  0  0  0
  7 21  1  6  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 14  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1

> <INCHI_KEY>
PIJVFDBKTWXHHD-HIFRSBDPSA-N

> <FORMULA>
C15H21N3O2

> <MOLECULAR_WEIGHT>
275.3461

> <EXACT_MASS>
275.163376931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.618093581107985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
2.2325330733333337

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.772488335318307

> <JCHEM_PKA_STRONGEST_BASIC>
6.585999039777742

> <JCHEM_POLAR_SURFACE_AREA>
44.81

> <JCHEM_REFRACTIVITY>
78.39679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
physostigmine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 981                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.655   0.127   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.090   2.734   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      14.534  -1.277   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      12.822   1.091   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.115   0.941   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.052  -1.279   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.298  -0.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.529  -2.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.806  -0.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.060  -2.732   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.282   1.091   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.806  -2.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.000  -0.803   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.243  -0.731   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.727   2.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.227   2.300   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.160   0.453   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.656   1.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.620   1.267   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   2.082   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      14.296   0.349   0.000  0.00  0.00           H+0
CONECT    1   17   19                                                       
CONECT    2   19                                                            
CONECT    3    7   10   13                                                  
CONECT    4    7   11   15                                                  
CONECT    5   19   20                                                       
CONECT    6    7    8    9   12                                             
CONECT    7    3    4    6   21                                             
CONECT    8    6   10                                                       
CONECT    9    6   11   14                                                  
CONECT   10    3    8                                                       
CONECT   11    4    9   16                                                  
CONECT   12    6                                                            
CONECT   13    3                                                            
CONECT   14    9   17                                                       
CONECT   15    4                                                            
CONECT   16   11   18                                                       
CONECT   17    1   14   18                                                  
CONECT   18   16   17                                                       
CONECT   19    1    2    5                                                  
CONECT   20    5                                                            
CONECT   21    7                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Antilirium	ChEBI
Eserine	ChEBI
Physostol	ChEBI
Erserine	HMDB
Eserine sulfate	HMDB
Eserolein, methylcarbamate	HMDB

Chemical Formula

C₁₅H₂₁N₃O₂

Average Mass

275.3461 Da

Monoisotopic Mass

275.16338 Da

IUPAC Name

(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate

Traditional Name

physostigmine

CAS Registry Number

Not Available

SMILES

[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C

InChI Identifier

InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1

InChI Key

PIJVFDBKTWXHHD-HIFRSBDPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chimonanthus fragrans	Plant	KNApSAcK
Physostigma venenosum	Plant	KNApSAcK
Streptomyces albospinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Indole
Dialkylarylamine
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Carbamic acid ester
Carbonic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:27953 )
indole alkaloid (CHEBI:27953 )
Alkaloids (C06535 )
Pyrroloindole alkaloids (C06535 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.8	ALOGPS
logP	2.23	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	6.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.4 m³·mol⁻¹	ChemAxon
Polarizability	30.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon