(2S,4R,5S)-Muscarine
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Basic Info
| Common Name | (2S,4R,5S)-Muscarine(F04683) |
| 2D Structure | |
| 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. |
| FRCD ID | F04683 |
| CAS Number | 300-54-9 |
| PubChem CID | 5079496 |
| Formula | C9H20NO2+ |
| IUPAC Name | (4-hydroxy-5-methyloxolan-2-yl)methyl-trimethylazanium |
| InChI Key | UQOFGTXDASPNLL-UHFFFAOYSA-N |
| InChI | 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 |
| Canonical SMILES | CC1C(CC(O1)C[N+](C)(C)C)O |
| Isomeric SMILES | CC1C(CC(O1)C[N+](C)(C)C)O |
| Wikipedia | (2S,4R,5S)-Muscarine |
| Synonyms |
(4-hydroxy-5-methyloxolan-2-yl)methyl-trimethylazanium
(2S,4R,5S)-Muscarine
Muscarine II
AC1NNZ0F
CHEMBL404094
SCHEMBL17428402
[(4-hydroxy-5-methyloxolan-2-yl)methyl]trimethylazanium
Trimethyl(tetrahydro-4-hydroxy-5-methylfurfuryl)-Ammonium
Tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-2-furanmethanaminium
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Monosaccharides |
| Direct Parent | Pentoses |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 174.264 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 153 |
| Monoisotopic Mass | 174.149 |
| Exact Mass | 174.149 |
| XLogP | 0.1 |
| Formal Charge | 1 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 3 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
Targets
- 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
- Mechanism of Action:
- Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors.
References
- Wikipedia. Muscarine. Last Updated 3 July 2009. : http://en.wikipedia.org/wiki/Muscarine
- 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
- Mechanism of Action:
- Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors.
References
- Wikipedia. Muscarine. Last Updated 3 July 2009. : http://en.wikipedia.org/wiki/Muscarine
- 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
- Mechanism of Action:
- Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors.
References
- Wikipedia. Muscarine. Last Updated 3 July 2009. : http://en.wikipedia.org/wiki/Muscarine
- 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
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 ]
- 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
- Mechanism of Action:
- Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors.
References
- Wikipedia. Muscarine. Last Updated 3 July 2009. : http://en.wikipedia.org/wiki/Muscarine
- 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
- Mechanism of Action:
- Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors.
References
- Wikipedia. Muscarine. Last Updated 3 July 2009. : http://en.wikipedia.org/wiki/Muscarine
- 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
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 ]
- 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
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 ]