ContaminantDB: Physostigmine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 01:30:59 UTC

Update Date

2016-11-09 01:09:15 UTC

Accession Number

CHEM003968

Identification

Common Name

Physostigmine

Class

Small Molecule

Description

A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₁₅H₂₁N₃O₂

Average Molecular Mass

275.346 g/mol

Monoisotopic Mass

275.163 g/mol

CAS Registry Number

57-47-6

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

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.99 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-1590000000-508da23acfe2c8a2f568	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ea-6790000000-c7dad12610a8d73fb915	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-1590000000-508da23acfe2c8a2f568	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ea-6790000000-c7dad12610a8d73fb915	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-3290000000-ff0ad85b80701aa56609	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03dj-2900000000-b9d164a9a3afaf8a17cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00or-0090000000-1f322550abc600bd72a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0490000000-e4a06a93b3b18d738157	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-d9ddac609ada184032ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-ef8f7c2ddbdba70fe1d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01ot-0900000000-daf3030c2c85de1db72e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-014i-0090000000-8a9155530ad88f483e2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03dj-2900000000-b9d164a9a3afaf8a17cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03di-0900000000-d3eb59c5c9b1e38fcb05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03xr-0960000000-5c126e885fa694d4eeac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-a1155e879f5d35d96bb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-016r-0090000000-5864a0721423095f52ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-016r-0090000000-5fdb9bd8096eedcd6a56	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0002-0900000000-d4927334d1d827874b42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-0960000000-11d52cd0d5583d0e2c27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-0950000000-e238974d00c6c1a74ff8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-0910000000-f5b98a709049c6a598e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0190000000-5bee8bebe8f73ca69075	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-016r-0090000000-77bf45d5232f86cce363	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-3090000000-4d4b520473a9f2047c89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-3090000000-a96a130ca2964214aa50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pdi-9440000000-97f447b7b63d60cd222b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-8090000000-c4df4baeb1b2ed495e64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-6090000000-03d5fd62a0bf34c26c01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9380000000-7df539c4225faf494471	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00981

HMDB ID

HMDB0015116

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001757

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Physostigmine (CHEM003968)

Structure for CHEM003968: Physostigmine