cis-Chlordane (CED0000042)

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:00 UTC

Update Date

2026-04-05 10:22:18 UTC

Accession Number

CHEM000055

Identification

Common Name

cis-Chlordane

Class

Small Molecule

Description

cis-Chlordane is an exogenous organic compound with the formula C10H6Cl8 and an average molecular weight of 409.78 g/mol. It exists as a liquid at room temperature. cis-Chlordane belongs to the vinyl chlorides, a subclass of vinyl halides within the organic compounds. The compound has been found in or released from food, food processing, and cookware food contact materials, with recorded exposure routes including inhalation, oral, and touch. cis-Chlordane interacts with thirteen recorded protein targets. It inhibits alkaline phosphatases in renal and hepatic tissues, specifically targeting the tissue-nonspecific isozyme of alkaline phosphatase (ALPL). It induces hepatic cytochrome P-450, including CYP2B6, CYP3A4, CYP3A43, and CYP3A5, which causes hepatocellular hypertrophy and a large increase in the volume of the smooth endoplasmic reticulum. Furthermore, cis-Chlordane causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor (ESR1 and ESR2). It antagonizes estrogen-related receptors, affecting transcription through ESRRG, ESRRA, and ESRRB. Developmental defects are caused by the binding and activation of retinoic acid receptor beta (RARB) and retinoic acid receptor gamma (RARG). Additionally, cis-Chlordane is believed to bind irreversibly to DNA, which leads to altered cellular function or cell death.

Contaminant Type

Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₀H₆Cl₈

Average Molecular Mass

409.779 g/mol

Monoisotopic Mass

405.798 g/mol

CAS Registry Number

5103-71-9

IUPAC Name

(1R,3R,4S,7S)-1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0²,⁶]dec-8-ene

Traditional Name

(1R,3R,4S,7S)-1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0²,⁶]dec-8-ene

SMILES

[H][C@]1(Cl)CC2([H])C([H])([C@@]1([H])Cl)[C@@]1(Cl)C(Cl)=C(Cl)[C@]2(Cl)C1(Cl)Cl

InChI Identifier

InChI=1S/C10H6Cl8/c11-3-1-2-4(5(3)12)9(16)7(14)6(13)8(2,15)10(9,17)18/h2-5H,1H2/t2?,3-,4?,5-,8-,9+/m0/s1

InChI Key

BIWJNBZANLAXMG-MRAITHJBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Vinyl halides

Sub Class

Vinyl chlorides

Direct Parent

Vinyl chlorides

Alternative Parents

Substituents

Chloroalkene
Haloalkene
Vinyl chloride
Hydrocarbon derivative
Organochloride
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

Extracellular
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

Liquid

Appearance

Colorless to amber liquid.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	5.6e-05 mg/mL at 25 °C [MABEY,WR et al. (1981)]

Predicted Properties

Property	Value	Source
Water Solubility	6.9e-05 g/L	ALOGPS
logP	6.02	ALOGPS
logP	5.27	ChemAxon
logS	-6.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.38 m³·mol⁻¹	ChemAxon
Polarizability	32.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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 LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0001900000-cbe0d008d48efeebddc7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0004900000-b9d20b4f44fa679d7984	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-2119000000-8e3e670086348c43ae15	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0001900000-11a7620b8bbb40ee8c05	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gb9-0009400000-73bfd1e73d846959f213	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0159-1009000000-3ce6dcfd1ccf213fc417	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Chlordane is believed to bind irreversibly to DNA, leading to cell death or altered cellular function. It also affects transcription by antagonizing estrogen-related receptors. Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. Chlordane has also been shown to bind and activate retinoic acid receptor, causing various developmental defects, and inhibit alkaline phosphatases in hepatic and renal tissues. (7, 1, 2, 3, 4)

Carcinogenicity (IARC Classification)

Chlordane is possibly carcinogenic to humans (Group 2B). (9)

Minimum Risk Level

Intermediate Inhalation: 0.0002 mg/m3 (8) Chronic Inhalation: 0.00002 mg/m3 (8) Acute Oral: 0.001 mg/kg/day (8) Intermediate Oral: 0.0006 mg/kg/day (8) Chronic Oral: 0.0006 mg/kg/day (8)

Symptoms

Ingestion and inhalation of chlordane cause headaches, irritability, confusion, weakness, vision problems, vomiting, stomach cramps, diarrhea, and jaundice. (7)

Treatment

Treatment is symptomatic. It is aimed at controlling convulsions, coma, and respiratory depression. Gastric lavage, followed by the administration of activated charcoal, may be performed following ingestion. (10)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
200.0	mg/kg	Not Available	Rat	LD50	Oral	experimental	T13
343.0	mg/kg	Not Available	Rat	LD50	Intraperitoneal	experimental	T13
10.0	mg/kg	Not Available	Mouse	LD50	Intravenous	experimental	T14
780.0	mg/kg	Not Available	Rat	LD50	Dermal	experimental	T14
100.0	mg/m3	Not Available	Cat	LC50	Inhalation (4 hours)	experimental	T14

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
494	Food contact materials	Food, food processing & cookware	Not Available

Pathways

1 pathway

Degradation Of Aromatic Compounds

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	histidine kinase	O32393	Arthrospira platensis	Predicted (SEA)	0.233548
Click to view 3D structure	GABA receptor subunit	Q75NA5	Musca domestica	Predicted (SEA)	0.0778492
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-3	P28472	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-1	P24046	Humans	Predicted (SEA)	98.3236
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	7767.09
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	7677.72
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	7676.48
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	7578.7
Click to view 3D structure	WD repeat-containing protein 91	A4D1P6	Humans	Predicted (SEA)	2591.44
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	7767.33
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	7713.85
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	7772.31
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	7770.91
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	7777.68
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	7778.93
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	7772.47
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	7778.69
Click to view 3D structure	Kynurenine 3-monooxygenase	P38169	Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)	Predicted (SEA)	1755.42
Click to view 3D structure	Lysine-specific histone demethylase 1A	O60341	Humans	Predicted (SEA)	7664.41
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	7716.96
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	7770.83
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	7776.83
Click to view 3D structure	Transporter	Q63380	Rattus norvegicus	Predicted (SEA)	7318.45
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	7754.41
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	7780.02
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Known	Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. (L91, A68)
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. (L91, A68)
Click to view 3D structure	Cytochrome P450 3A43	Q9HB55	Humans	Known	Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. (L91, A68)
Click to view 3D structure	Cytochrome P450 3A5	P20815	Humans	Known	Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. (L91, A68)
Click to view 3D structure	Cytochrome P450 3A7	P24462	Humans	Known	Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. (L91, A68)
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	Alkaline phosphatase, tissue-nonspecific isozyme	P05186	Humans	Known	Chlordane inhibit alkaline phosphatases in hepatic and renal tissues. (A69)
Click to view 3D structure	Estrogen-related receptor gamma	P62508	Humans	Known	Chlordane affects transcription by antagonizing estrogen-related receptors. (A52)
Click to view 3D structure	Retinoic acid receptor beta	P10826	Humans	Known	Chlordane has been shown to bind and activate retinoic acid receptor, causing various developmental defects. (A53)
Click to view 3D structure	Retinoic acid receptor gamma	P13631	Humans	Known	Chlordane has been shown to bind and activate retinoic acid receptor, causing various developmental defects. (A53)
Click to view 3D structure	Steroid hormone receptor ERR1	P11474	Humans	Known	Chlordane affects transcription by antagonizing estrogen-related receptors. (A52)
Click to view 3D structure	Steroid hormone receptor ERR2	O95718	Humans	Known	Chlordane affects transcription by antagonizing estrogen-related receptors. (A52)