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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:19:52 UTC
HMDB IDHMDB0015116
Secondary Accession Numbers
  • HMDB15116
Metabolite Identification
Common NamePhysostigmine
DescriptionPhysostigmine, 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. Physostigmine is a very strong basic compound (based on its pKa).
Structure
Data?1582753260
Synonyms
ValueSource
AntiliriumChEBI
EserineChEBI
PhysostolChEBI
ErserineHMDB
Eserine sulfateHMDB
Eserolein, methylcarbamateHMDB
Chemical FormulaC15H21N3O2
Average Molecular Weight275.3461
Monoisotopic Molecular Weight275.163376931
IUPAC Name(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
Traditional Namephysostigmine
CAS Registry Number57-47-6
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 KeyPIJVFDBKTWXHHD-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point105.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.99 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available167.899http://allccs.zhulab.cn/database/detail?ID=AllCCS00000978
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.99 g/LALOGPS
logP10(1.8) g/LALOGPS
logP10(2.23) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)14.77ChemAxon
pKa (Strongest Basic)6.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.81 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.4 m³·mol⁻¹ChemAxon
Polarizability30.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.431661259
DarkChem[M-H]-164.07531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Physostigmine[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C3403.6Standard polar33892256
Physostigmine[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C2214.4Standard non polar33892256
Physostigmine[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C2299.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Physostigmine,1TMS,isomer #1CN1CC[C@@]2(C)C3=CC(OC(=O)N(C)[Si](C)(C)C)=CC=C3N(C)[C@@H]122241.0Semi standard non polar33892256
Physostigmine,1TMS,isomer #1CN1CC[C@@]2(C)C3=CC(OC(=O)N(C)[Si](C)(C)C)=CC=C3N(C)[C@@H]122316.9Standard non polar33892256
Physostigmine,1TMS,isomer #1CN1CC[C@@]2(C)C3=CC(OC(=O)N(C)[Si](C)(C)C)=CC=C3N(C)[C@@H]122676.5Standard polar33892256
Physostigmine,1TBDMS,isomer #1CN1CC[C@@]2(C)C3=CC(OC(=O)N(C)[Si](C)(C)C(C)(C)C)=CC=C3N(C)[C@@H]122461.1Semi standard non polar33892256
Physostigmine,1TBDMS,isomer #1CN1CC[C@@]2(C)C3=CC(OC(=O)N(C)[Si](C)(C)C(C)(C)C)=CC=C3N(C)[C@@H]122536.4Standard non polar33892256
Physostigmine,1TBDMS,isomer #1CN1CC[C@@]2(C)C3=CC(OC(=O)N(C)[Si](C)(C)C(C)(C)C)=CC=C3N(C)[C@@H]122816.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Physostigmine GC-EI-TOF (Non-derivatized)splash10-001j-1590000000-508da23acfe2c8a2f5682017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Physostigmine GC-EI-TOF (Non-derivatized)splash10-00ea-6790000000-c7dad12610a8d73fb9152017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Physostigmine GC-EI-TOF (Non-derivatized)splash10-001j-1590000000-508da23acfe2c8a2f5682018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Physostigmine GC-EI-TOF (Non-derivatized)splash10-00ea-6790000000-c7dad12610a8d73fb9152018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Physostigmine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-3290000000-ff0ad85b80701aa566092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Physostigmine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Physostigmine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-qTof , Positive-QTOFsplash10-03dj-2900000000-b9d164a9a3afaf8a17cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-QQ , positive-QTOFsplash10-00or-0090000000-1f322550abc600bd72a92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-QQ , positive-QTOFsplash10-014i-0490000000-e4a06a93b3b18d7381572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-QQ , positive-QTOFsplash10-03di-0900000000-d9ddac609ada184032ac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-QQ , positive-QTOFsplash10-03di-0900000000-ef8f7c2ddbdba70fe1d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-QQ , positive-QTOFsplash10-01ot-0900000000-daf3030c2c85de1db72e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine LC-ESI-IT , positive-QTOFsplash10-014i-0090000000-8a9155530ad88f483e2e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine , positive-QTOFsplash10-03dj-2900000000-b9d164a9a3afaf8a17cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 6V, Positive-QTOFsplash10-03di-0900000000-d3eb59c5c9b1e38fcb052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 6V, Positive-QTOFsplash10-03xr-0960000000-5c126e885fa694d4eeac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 30V, Positive-QTOFsplash10-03di-0900000000-a1155e879f5d35d96bb72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 10V, Positive-QTOFsplash10-016r-0090000000-5864a0721423095f52ac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 6V, Positive-QTOFsplash10-016r-0090000000-5fdb9bd8096eedcd6a562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 50V, Positive-QTOFsplash10-0002-0900000000-d4927334d1d827874b422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 10V, Positive-QTOFsplash10-03xr-0960000000-11d52cd0d5583d0e2c272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 10V, Positive-QTOFsplash10-03xr-0950000000-e238974d00c6c1a74ff82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 35V, Positive-QTOFsplash10-03di-0910000000-f5b98a709049c6a598e02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 15V, Positive-QTOFsplash10-014i-0190000000-5bee8bebe8f73ca690752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Physostigmine 10V, Positive-QTOFsplash10-016r-0090000000-77bf45d5232f86cce3632021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physostigmine 10V, Positive-QTOFsplash10-00or-3090000000-4d4b520473a9f2047c892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physostigmine 20V, Positive-QTOFsplash10-0uxr-3090000000-a96a130ca2964214aa502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physostigmine 40V, Positive-QTOFsplash10-0pdi-9440000000-97f447b7b63d60cd222b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physostigmine 10V, Negative-QTOFsplash10-0ab9-8090000000-c4df4baeb1b2ed495e642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physostigmine 20V, Negative-QTOFsplash10-0a4i-6090000000-03d5fd62a0bf34c26c012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physostigmine 40V, Negative-QTOFsplash10-0pb9-9380000000-7df539c4225faf4944712016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00981 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00981 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00981
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001757
Chemspider ID5763
KEGG Compound IDC06535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhysostigmine
METLIN IDNot Available
PubChem Compound5983
PDB IDNot Available
ChEBI ID27953
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

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
  1. Nguyen PV, Aniksztejn L, Catarsi S, Drapeau P: Maturation of neuromuscular transmission during early development in zebrafish. J Neurophysiol. 1999 Jun;81(6):2852-61. [PubMed:10368402 ]
  2. Tuovinen K, Kaliste-Korhonen E, Raushel FM, Hanninen O: Success of pyridostigmine, physostigmine, eptastigmine and phosphotriesterase treatments in acute sarin intoxication. Toxicology. 1999 Jun 15;134(2-3):169-78. [PubMed:10403635 ]
  3. Blasina MF, Faria AC, Gardino PF, Hokoc JN, Almeida OM, de Mello FG, Arruti C, Dajas F: Evidence for a noncholinergic function of acetylcholinesterase during development of chicken retina as shown by fasciculin. Cell Tissue Res. 2000 Feb;299(2):173-84. [PubMed:10741458 ]
  4. Monnet-Tschudi F, Zurich MG, Schilter B, Costa LG, Honegger P: Maturation-dependent effects of chlorpyrifos and parathion and their oxygen analogs on acetylcholinesterase and neuronal and glial markers in aggregating brain cell cultures. Toxicol Appl Pharmacol. 2000 Jun 15;165(3):175-83. [PubMed:10873710 ]
  5. Bolognesi ML, Andrisano V, Bartolini M, Minarini A, Rosini M, Tumiatti V, Melchiorre C: Hexahydrochromeno[4,3-b]pyrrole derivatives as acetylcholinesterase inhibitors. J Med Chem. 2001 Jan 4;44(1):105-9. [PubMed:11141093 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]