T3DB: (2S,4R,5S)-Muscarine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (8)XML

Targets (8)

Record Information

Version

2.0

Creation Date

2009-07-03 20:53:35 UTC

Update Date

2014-12-24 20:25:31 UTC

Accession Number

T3D2452

Identification

Common Name

(2S,4R,5S)-Muscarine

Class

Small Molecule

Description

Main toxic constituent of the fly fungus Amanita muscaria and various Inocybe species (2S,4R,5S)-Muscarine belongs to the family of Oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Compound Type

Ether
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
(+)-(2S,4R,5S)-Muscarine
(+)-muscarine
L-(+)-Muscarine
Muscarin
Muscarine
Muscarine (alkaloid)
Muscarine (the alkaloid)
Muscarine chloride
Muscarine II
Muskarin
Trimethyl(tetrahydro-4-hydroxy-5-methylfurfuryl)-Ammonium

Chemical Formula

C₉H₂₀NO₂

Average Molecular Mass

174.260 g/mol

Monoisotopic Mass

174.149 g/mol

CAS Registry Number

300-54-9

IUPAC Name

{[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium

Traditional Name

(+)-muscarine

SMILES

[H][C@@]1(C)O[C@]([H])(C[N+](C)(C)C)C[C@@]1([H])O

InChI Identifier

InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1

InChI Key

InChIKey=UQOFGTXDASPNLL-XHNCKOQMSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Quaternary ammonium salt
Tetraalkylammonium salt
Tetrahydrofuran
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organic salt
Alcohol
Organic cation
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monosaccharide (CHEBI:7034 )
Alkaloids (C07473 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

Solid

Appearance

White powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.3	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.11	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.89 m³·mol⁻¹	ChemAxon
Polarizability	20.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-0f9y-6900000000-79763ab7b63262ffe2c2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00di-0900000000-c226ed17dd770fa6c411	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-00di-2900000000-67eb26beea6d618ebb7d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-00di-5900000000-4e0964583deb72b35ef6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-05fr-9500000000-a0a0c909b980bb4769c2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0a4i-9200000000-be98c82a4035b83f8750	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0a4i-9100000000-e8830a6e2498d5ca0b6f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0a4i-9000000000-19f49df6db6e4b92cf3d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0a4l-9000000000-0755c01a97b2a22de481	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0a4l-9000000000-b0b62b0c3630f7342703	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-052f-9000000000-0a2f7b3f7e5bf0ef5ed3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-052f-9000000000-24069c492c822c8073ed	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00di-0900000000-e02b9884b570bdfc5d5c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00di-2900000000-1be2813c25bfaa5cb10c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-05fr-9600000000-cb4c5b9dc39c97a63239	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0c00-9100000000-2e0e0d8c33dd5405906b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0bt9-9000000000-1c66632fe3ec85e7e9b7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-0bt9-9000000000-b821cc1b0c3b1409a2a4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, positive	splash10-0a4i-9000000000-4556237f549b235f4c6e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, positive	splash10-014i-4900000000-2e898bb2167bdd163be9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, positive	splash10-0a4i-9000000000-e58e4ee62799955c0939	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0900000000-a0080208160655ea0b73	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-2900000000-9edf94eafe412073184c	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9100000000-c8c1131f5df11bfdcd19	2019-02-22	View Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

Mechanism of Toxicity

Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (3)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. (3)

Minimum Risk Level

Not Available

Health Effects

Intoxication generally subsides within 2 hours. Death is rare, but may result from cardiac or respiratory failure in severe cases. (3)

Symptoms

Muscarine poisoning is characterized by increased salivation, sweating (perspiration), and tearflow (lacrimation) within 15 to 30 minutes after ingestion of the mushroom. With large doses, these symptoms may be followed by abdominal pain, severe nausea, diarrhea, blurred vision, and labored breathing. (3)

Treatment

The specific antidote is atropine. (3)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB29936

PubChem Compound ID

5079496

ChEMBL ID

Not Available

ChemSpider ID

4255959

KEGG ID

C07473

UniProt ID

Not Available

OMIM ID

ChEBI ID

522933

BioCyc ID

Not Available

CTD ID

D009116

Stitch ID

Muscarine

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Muscarine

References

Synthesis Reference

Not Available

MSDS

T3D2452.pdf

General References

Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Wikipedia. Muscarine. Last Updated 3 July 2009. [Link]
Wikipedia. Mushroom poisoning. Last Updated 10 August 2009. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Muscarinic acetylcholine receptor M2

General Function:: G-protein coupled acetylcholine receptor activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular Weight:: 51714.605 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	0.025 uM	Not Available	BindingDB 50008066
Inhibitory	0.072 uM	Not Available	BindingDB 50008066
Inhibitory	0.075 uM	Not Available	BindingDB 50008066
IC50	0.49 uM	Not Available	BindingDB 50008066
IC50	3.9 uM	Not Available	BindingDB 50008066

References

Pei XF, Gupta TH, Badio B, Padgett WL, Daly JW: 6beta-Acetoxynortropane: a potent muscarinic agonist with apparent selectivity toward M2-receptors. J Med Chem. 1998 Jun 4;41(12):2047-55. [9622546 ]
Daly JW, Gupta TH, Padgett WL, Pei XF: 6beta-Acyloxy(nor)tropanes: affinities for antagonist/agonist binding sites on transfected and native muscarinic receptors. J Med Chem. 2000 Jun 29;43(13):2514-22. [10891110 ]

Target Details

2. Muscarinic acetylcholine receptor M4

General Function:: Guanyl-nucleotide exchange factor activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:: CHRM4
Uniprot ID:: P08173
Molecular Weight:: 53048.65 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	0.023 uM	Not Available	BindingDB 50008066
Inhibitory	1.4 uM	Not Available	BindingDB 50008066
Inhibitory	28 uM	Not Available	BindingDB 50008066

References

Daly JW, Gupta TH, Padgett WL, Pei XF: 6beta-Acyloxy(nor)tropanes: affinities for antagonist/agonist binding sites on transfected and native muscarinic receptors. J Med Chem. 2000 Jun 29;43(13):2514-22. [10891110 ]
Pei XF, Gupta TH, Badio B, Padgett WL, Daly JW: 6beta-Acetoxynortropane: a potent muscarinic agonist with apparent selectivity toward M2-receptors. J Med Chem. 1998 Jun 4;41(12):2047-55. [9622546 ]

Target Details

3. Acetylcholine receptor subunit alpha

General Function:: Ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNA1
Uniprot ID:: P02708
Molecular Weight:: 54545.235 Da

References

Wikipedia. Muscarine. Last Updated 3 July 2009. [Link]

Target Details

4. Acetylcholine receptor subunit beta

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNB1
Uniprot ID:: P11230
Molecular Weight:: 56697.9 Da

References

Wikipedia. Muscarine. Last Updated 3 July 2009. [Link]

Target Details

5. Acetylcholine receptor subunit delta

General Function:: Acetylcholine-activated cation-selective channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRND
Uniprot ID:: Q07001
Molecular Weight:: 58894.55 Da

References

Wikipedia. Muscarine. Last Updated 3 July 2009. [Link]

Target Details

6. Acetylcholine receptor subunit epsilon

General Function:: Cation transmembrane transporter activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNE
Uniprot ID:: Q04844
Molecular Weight:: 54696.54 Da

References

Wikipedia. Muscarine. Last Updated 3 July 2009. [Link]

Target Details

7. Acetylcholine receptor subunit gamma

General Function:: Channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNG
Uniprot ID:: P07510
Molecular Weight:: 57882.8 Da

References

Wikipedia. Muscarine. Last Updated 3 July 2009. [Link]

Target Details

8. Muscarinic acetylcholine receptor M1

General Function:: Phosphatidylinositol phospholipase c activity
Specific Function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular Weight:: 51420.375 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	0.056 uM	Not Available	BindingDB 50008066

References

Daly JW, Gupta TH, Padgett WL, Pei XF: 6beta-Acyloxy(nor)tropanes: affinities for antagonist/agonist binding sites on transfected and native muscarinic receptors. J Med Chem. 2000 Jun 29;43(13):2514-22. [10891110 ]

(2S,4R,5S)-Muscarine (T3D2452)

Structure for T3D2452: (2S,4R,5S)-Muscarine

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

References

References

References

References

References

Binding/Activity Constants

References