Toxiferine
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Basic Info
| Common Name | Toxiferine(F04811) |
| 2D Structure | |
| Description | Toxiferine is a type of curare, a plant toxin known for its use as paralyzing arrow poison by South American indigenous people. It can be extracted from a variety of plants, including Strychnos toxifera and Chondrodendron tomentosum. Curares are active only by an injection. They are harmless if taken orally because curare compounds are too large and too highly charged to pass through the lining of the digestive tract to be absorbed into the blood. (L1256) |
| FRCD ID | F04811 |
| CAS Number | 6888-23-9 |
| PubChem CID | 5281411 |
| Formula | C40H46N4O2+2 |
| IUPAC Name | None |
| InChI Key | IIYHWTVUYIYKKG-QQRSFBQTSA-N |
| InChI | InChI=1S/C40H46N4O2/c1-43-15-13-39-31-7-3-5-9-33(31)41-22-30-28-20-36-40(14-16-44(36,2)24-26(28)12-18-46)32-8-4-6-10-34(32)42(38(30)40)21-29(37(39)41)27(19-35(39)43)25(23-43)11-17-45/h3-12,21-22,27-28,35-38,45-46H,13-20,23-24H2,1-2H3/q+2/b25-11-,26-12-,29-21-,30-22-/t27-,28-,35-,36-,37-,38-,39+,40+,43-,44-/m0/s1 |
| Canonical SMILES | C[N+]12CCC34C1CC(C(=CCO)C2)C5=CN6C7C(=CN(C53)C8=CC=CC=C48)C9CC1C7(CC[N+]1(CC9=CCO)C)C1=CC=CC=C16 |
| Isomeric SMILES | C[N@@+]12[C@@H]3[C@]4(C5=CC=CC=C5N/6[C@H]4/C(=C\N7[C@H]8/C(=C6)/[C@@H]9/C(=C\CO)/C[N@+]4([C@H]([C@]8(C5=CC=CC=C75)CC4)C9)C)/[C@@H](C3)/C(=C\CO)/C1)CC2 |
| Wikipedia | Toxiferine |
| Synonyms |
TOXIFERINE
UNII-9M7D9K3OJI
Toxiferine I
9M7D9K3OJI
CHEBI:9644
Toxiferine I, 2,2',16,16'-tetradehydro-16,16',17,17'-tetrahydro-
C-Toxiferine I
302-30-7
C40H46N4O2
D0M8JZ
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Strychnos alkaloids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Strychnos alkaloids |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Strychnan skeleton - Akuammicine-skeleton - Curan skeleton - Stemmadenine-skeleton - Carbazole - Indole or derivatives - Indolizidine - Tertiary aliphatic/aromatic amine - Aralkylamine - Benzenoid - Piperidine - N-alkylpyrrolidine - Tetraalkylammonium salt - Pyrrolidine - Quaternary ammonium salt - Tertiary amine - Organoheterocyclic compound - Enamine - Azacycle - Allylamine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic salt - Organopnictogen compound - Amine - Organic oxygen compound - Alcohol - Organic nitrogen compound - Hydrocarbon derivative - Organic cation - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 614.834 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 1390 |
| Monoisotopic Mass | 614.362 |
| Exact Mass | 614.362 |
| XLogP | 1.8 |
| Formal Charge | 2 |
| Heavy Atom Count | 46 |
| Defined Atom Stereocenter Count | 10 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 4 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
Targets
- 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:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Receptor binding
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
- Gene Name:
- CHRNA10
- Uniprot ID:
- Q9GZZ6
- Molecular Weight:
- 49704.295 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Drug binding
- 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:
- CHRNA2
- Uniprot ID:
- Q15822
- Molecular Weight:
- 59764.82 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- CHRNA3
- Uniprot ID:
- P32297
- Molecular Weight:
- 57479.54 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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 permeable to sodium ions.
- Gene Name:
- CHRNA4
- Uniprot ID:
- P43681
- Molecular Weight:
- 69956.47 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- CHRNA5
- Uniprot ID:
- P30532
- Molecular Weight:
- 53053.965 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- CHRNA6
- Uniprot ID:
- Q15825
- Molecular Weight:
- 56897.745 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Toxic substance binding
- 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. The channel is blocked by alpha-bungarotoxin.
- Gene Name:
- CHRNA7
- Uniprot ID:
- P36544
- Molecular Weight:
- 56448.925 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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 permeable to sodiun ions.
- Gene Name:
- CHRNB2
- Uniprot ID:
- P17787
- Molecular Weight:
- 57018.575 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Drug binding
- 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:
- CHRNB3
- Uniprot ID:
- Q05901
- Molecular Weight:
- 52728.215 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- 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:
- CHRNB4
- Uniprot ID:
- P30926
- Molecular Weight:
- 56378.985 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Calcium channel activity
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
- Gene Name:
- CHRNA9
- Uniprot ID:
- Q9UGM1
- Molecular Weight:
- 54806.63 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare