Endrin ketone (CED0000045)

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:00 UTC

Update Date

2026-08-18 21:38:07 UTC

Accession Number

CHEM000059

Identification

Common Name

Endrin ketone

Class

Small Molecule

Description

Endrin ketone is an exogenous solid with the chemical formula C12H8Cl6O and an average molecular weight of 380.91 g/mol. Endrin ketone belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. This compound is used in Low-Density Polyethylene. The compound interacts with 32 recorded protein targets. It inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, including Calcium-transporting ATPase type 2C member 1 (ATP2C1), Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (ATP2A1), Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (ATP2A2), and Sodium/potassium-transporting ATPase subunit gamma (FXYD2), among seven other proteins. This inhibition disrupts the transport of calcium across membranes, leading to the accumulation of intracellular free calcium ions, which promotes the release of neurotransmitters from storage vesicles, the depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Additionally, endrin ketone antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) at GABA-A receptors, involving Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), subunit alpha-2 (GABRA2), subunit alpha-3 (GABRA3), subunit alpha-4 (GABRA4), and 15 other proteins. This action blocks the GABA-induced uptake of chloride ions, resulting in hyperexcitability of the central nervous system. Endrin ketone also causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor, specifically the Estrogen receptor (ESR1) and Estrogen receptor beta (ESR2).

Contaminant Type

Ketone
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₂H₈Cl₆O

Average Molecular Mass

380.909 g/mol

Monoisotopic Mass

377.871 g/mol

CAS Registry Number

53494-70-5

IUPAC Name

1,2,2,3,10,11-hexachloropentacyclo[5.4.1.0³,¹⁰.0⁴,¹².0⁵,⁹]dodecan-8-one

Traditional Name

endrin ketone

SMILES

ClC1C2(Cl)C3C4CC5C3C(Cl)(C2(Cl)Cl)C1(Cl)C5C4=O

InChI Identifier

InChI=1S/C12H8Cl6O/c13-8-9(14)6-2-1-3(7(6)19)4-5(2)11(9,16)12(17,18)10(4,8)15/h2-6,8H,1H2

InChI Key

IZHZFAQWVKBTSL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Norbornane monoterpenoid
Monoterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	4.81	ALOGPS
logP	4.32	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	16.21	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.56 m³·mol⁻¹	ChemAxon
Polarizability	31.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-1009000000-ced2237af233142259e1	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-8e613083c8c5c9d9096c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-1ecb77c0bc1a680f738e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-074i-0009000000-8ee6f9e70d69653aee90	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-9f55adbc187a907df215	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-0009000000-cd445e23a1615eaabd05	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-94646193439a2afd5885	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-bbc098baf89f49ef5fc5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-bbc098baf89f49ef5fc5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-8639ead38b1f2cd8f1ff	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-e47142fe4621b138f5c3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9004000000-c00711d39b2dff01c12c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0059-4009000000-891aea2a3319a25fee84	Not Available	View Spectrum
MS	MS Spectrum	splash10-014i-6953000000-47ad59acadbfa012d499	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. Endrin also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Endrin also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (4, 2)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Symptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (2)

Treatment

Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (3)

Toxicity Values

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	histidine kinase	O32393	Arthrospira platensis	Predicted (SEA)	101.671
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	7170.77
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	7714.86
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	7679.51
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	7684.03
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	7725.21
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	7737.36
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-4	P28471	Rattus norvegicus	Predicted (SEA)	105.486
Click to view 3D structure	A disintegrin and metalloproteinase with thrombospondin motifs 5	Q9UNA0	Humans	Predicted (SEA)	7445.89
Click to view 3D structure	Disintegrin and metalloproteinase domain-containing protein 17	P78536	Humans	Predicted (SEA)	7653.36
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	7665.03
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	7771.53
Click to view 3D structure	Mitochondrial sodium/calcium exchanger protein	Q6J4K2	Humans	Predicted (SEA)	1488.48
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	7768.26
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	7763.9
Click to view 3D structure	Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform	Q76MZ3	Mus musculus	Predicted (SEA)	101.905
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	7296.18
Click to view 3D structure	A disintegrin and metalloproteinase with thrombospondin motifs 4	O75173	Humans	Predicted (SEA)	7533.78
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	1790.45
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	935.203
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	7768.96
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	7774.02
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	6791.25
Click to view 3D structure	Thymidine kinase 2	D3ZGQ2	Rattus norvegicus	Predicted (SEA)	3324.47
Click to view 3D structure	Prolyl endopeptidase	P48147	Humans	Predicted (SEA)	6784.56
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Known	Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Click to view 3D structure	Calcium-transporting ATPase type 2C member 1	P98194	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-1	P14867	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-2	P47869	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-3	P34903	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-4	P48169	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-5	P31644	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-6	Q16445	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-1	P18505	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-2	P47870	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-3	P28472	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit delta	O14764	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit epsilon	P78334	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit gamma-1	Q8N1C3	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit gamma-2	P18507	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit gamma-3	Q99928	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit pi	O00591	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-1	P24046	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-2	P28476	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-3	A8MPY1	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit theta	Q9UN88	Humans	Known	Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	O14983	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2	P16615	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-1	P05023	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-2	P50993	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-3	P13637	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-4	Q13733	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit beta-1	P05026	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit beta-2	P14415	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit beta-3	P54709	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit gamma	P54710	Humans	Known	Endrin inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)