Cicutoxin
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Basic Info
| Common Name | Cicutoxin(F04791) |
| 2D Structure | |
| Description | Cicutoxin is a plant toxin found in several species, most notably water hemlock (Cicuta species). It is a cholinergic poison, causing death by disruption of the central nervous system. (L1232) |
| FRCD ID | F04791 |
| CAS Number | 505-75-9 |
| PubChem CID | 5281132 |
| Formula | C17H22O2 |
| IUPAC Name | (8E,10E,12E)-heptadeca-8,10,12-trien-4,6-diyne-1,14-diol |
| InChI Key | FQVNSJQTSOVRKZ-YNQQSWPQSA-N |
| InChI | InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10,12,15,17-19H,2,11,13-14,16H2,1H3/b6-4+,10-8+,15-12+ |
| Canonical SMILES | CCCC(C=CC=CC=CC#CC#CCCCO)O |
| Isomeric SMILES | CCCC(/C=C/C=C/C=C/C#CC#CCCCO)O |
| Synonyms |
HSDB 3472
trans-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
AC1NQY2Z
SCHEMBL166718
8,10,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-
CHEMBL453245
NSC606489
NSC-606489
LS-74188
8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty alcohols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Long-chain fatty alcohols |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Long chain fatty alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 258.361 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 8 |
| Complexity | 429 |
| Monoisotopic Mass | 258.162 |
| Exact Mass | 258.162 |
| XLogP | 3.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Water hemlock poisoning in cattle: Ingestion of immature Cicuta maculata seed as the probable cause. | Toxicon | 2011 Jan | 21094658 |
Targets
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
- Gene Name:
- GABRA1
- Uniprot ID:
- P14867
- Molecular Weight:
- 51801.395 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA2
- Uniprot ID:
- P47869
- Molecular Weight:
- 51325.85 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA3
- Uniprot ID:
- P34903
- Molecular Weight:
- 55164.055 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA4
- Uniprot ID:
- P48169
- Molecular Weight:
- 61622.645 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA6
- Uniprot ID:
- Q16445
- Molecular Weight:
- 51023.69 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
- Gene Name:
- GABRB1
- Uniprot ID:
- P18505
- Molecular Weight:
- 54234.085 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
- Gene Name:
- GABRB2
- Uniprot ID:
- P47870
- Molecular Weight:
- 59149.895 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Gaba-gated chloride ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
- Gene Name:
- GABRB3
- Uniprot ID:
- P28472
- Molecular Weight:
- 54115.04 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Gaba-a receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRD
- Uniprot ID:
- O14764
- Molecular Weight:
- 50707.835 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRE
- Uniprot ID:
- P78334
- Molecular Weight:
- 57971.175 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRG1
- Uniprot ID:
- Q8N1C3
- Molecular Weight:
- 53594.49 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
- Gene Name:
- GABRG2
- Uniprot ID:
- P18507
- Molecular Weight:
- 54161.78 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRG3
- Uniprot ID:
- Q99928
- Molecular Weight:
- 54288.16 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Gaba-a receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the uterus, the function of the receptor appears to be related to tissue contractility. The binding of this pI subunit with other GABA(A) receptor subunits alters the sensitivity of recombinant receptors to modulatory agents such as pregnanolone.
- Gene Name:
- GABRP
- Uniprot ID:
- O00591
- Molecular Weight:
- 50639.735 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Gaba-a receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRR3
- Uniprot ID:
- A8MPY1
- Molecular Weight:
- 54271.1 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRQ
- Uniprot ID:
- Q9UN88
- Molecular Weight:
- 72020.875 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Transporter activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA5
- Uniprot ID:
- P31644
- Molecular Weight:
- 52145.645 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Gaba-a receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA receptor could play a role in retinal neurotransmission.
- Gene Name:
- GABRR1
- Uniprot ID:
- P24046
- Molecular Weight:
- 55882.91 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin
- General Function:
- Gaba-a receptor activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission.
- Gene Name:
- GABRR2
- Uniprot ID:
- P28476
- Molecular Weight:
- 54150.41 Da
- Mechanism of Action:
- Cicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor.
References
- Wikipedia. Cicutoxin. Last Updated 19 July 2009. : http://en.wikipedia.org/wiki/Cicutoxin