Cicutoxin (T3D3076)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (19)XML
Targets (19)
Record Information
Version2.0
Creation Date2009-07-23 18:26:05 UTC
Update Date2014-12-24 20:25:57 UTC
Accession NumberT3D3076
Identification
Common NameCicutoxin
ClassSmall Molecule
DescriptionCicutoxin 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. (2)
Compound Type
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
trans-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
Chemical FormulaC17H22O2
Average Molecular Mass258.355 g/mol
Monoisotopic Mass258.162 g/mol
CAS Registry Number505-75-9
IUPAC Nameheptadeca-8,10,12-trien-4,6-diyne-1,14-diol
Traditional Nameheptadeca-8,10,12-trien-4,6-diyne-1,14-diol
SMILESCCCC(O)C=CC=CC=CC#CC#CCCCO
InChI IdentifierInChI=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+
InChI KeyInChIKey=FQVNSJQTSOVRKZ-YNQQSWPQSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Long chain fatty alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point54°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.09ALOGPS
logP3.44ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity85.54 m³·mol⁻¹ChemAxon
Polarizability32.95 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0190000000-ea02c74c769eb20be5eb2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-5980000000-9ec364c80ce3a45dd34e2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9800000000-4d7d20aae89589467c202019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-d613262099df5ce837172019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2090000000-13a9b9be811e93243e2a2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9320000000-e3e5a8bd713a1a0c295d2019-02-23View Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (3) ; dermal (3)
Mechanism of ToxicityCicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor. (2)
MetabolismNot Available
Toxicity ValuesLD50: 48.3 mg/kg (Intraperitoneal, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCicutoxin is a plant toxin found in several species, most notably water hemlock (Cicuta species). (2)
Minimum Risk LevelNot Available
Health EffectsCicutoxin is a cholinergic poison and disrupts the central nervous system, leading to tremors, seizures, and death. (2)
SymptomsCicutoxin produces nausea, emesis and abdominal pain, typically within 60 minutes of ingestion. (2)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5281132
ChEMBL IDCHEMBL453245
ChemSpider ID4444576
KEGG IDC08402
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDCicutoxin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Lewis RJ Sr. (ed) (2004). Sax's Dangerous Properties of Industrial Materials. 11th Edition. Hoboken, NJ: Wiley-Interscience, Wiley & Sons, Inc.
  2. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
  3. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Gamma-aminobutyric acid receptor subunit alpha-1
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
2. Gamma-aminobutyric acid receptor subunit alpha-2
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
3. Gamma-aminobutyric acid receptor subunit alpha-3
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
4. Gamma-aminobutyric acid receptor subunit alpha-4
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
5. Gamma-aminobutyric acid receptor subunit alpha-5
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
6. Gamma-aminobutyric acid receptor subunit alpha-6
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
7. Gamma-aminobutyric acid receptor subunit beta-1
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
8. Gamma-aminobutyric acid receptor subunit beta-2
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
9. Gamma-aminobutyric acid receptor subunit beta-3
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
10. Gamma-aminobutyric acid receptor subunit delta
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
11. Gamma-aminobutyric acid receptor subunit epsilon
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
12. Gamma-aminobutyric acid receptor subunit gamma-1
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
13. Gamma-aminobutyric acid receptor subunit gamma-2
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
14. Gamma-aminobutyric acid receptor subunit gamma-3
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
15. Gamma-aminobutyric acid receptor subunit pi
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
16. Gamma-aminobutyric acid receptor subunit rho-1
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
17. Gamma-aminobutyric acid receptor subunit rho-2
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
18. Gamma-aminobutyric acid receptor subunit rho-3
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]
Target Details
19. Gamma-aminobutyric acid receptor subunit theta
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
References
  1. Wikipedia. Cicutoxin. Last Updated 19 July 2009. [Link]