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T3D0060 - Dibromochloropropane

Record Information
Version 1.0
Creation Date 2009-03-06 18:58:00 UTC
Update Date 2013-04-25 08:32:39 UTC
Accession Number T3D0060
Identification
Common Name Dibromochloropropane
Description Dibromochloropropane is a manufactured chemical and the active ingredient in the nematicide Nemagon, also known as Fumazone. Nemagon is a soil fumigant formerly used in agriculture but banned to most areas today. (R237)
Compound Type
  • Organic Compound
  • Organochloride
  • Pesticide
  • Organobromide
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. 1,2-Dibrom-3-chlor-propan [German]
  2. 1,2-Dibromo-3-chloropropane
  3. 1,2-Dibromo-3-chloropropane (DBCP)
  4. 1,2-Dibromo-3-cloro-propano [Italian]
  5. 1,2-Dibromochloropropane
  6. 1,2-Dibroom-3-chloorpropaan [Dutch]
  7. 1,3-Dibromo-3-chloropropane
  8. 1-Chloro-2,3-dibromopropane
  9. 2,3-Dibromo-1-chloropropane
  10. 3-Chloro-1,2-dibromopropane
  11. Dibromchlorpropan [german]
  12. Dibromochloropropane
  13. Gro-tone nematode granular
  14. Nemabrom
  15. Nemafume
  16. Nemagon soil fumigant
  17. Nemagone
  18. Nemanax
  19. Nemanex
  20. Nemapaz
  21. Nemaset
  22. Nematocide
  23. Nematox
  24. Nemazon
Chemical Formula C3H5Br2Cl
Average Molecular Weight 236.333
Monoisotopic Molecular Weight 233.844653161
Chemical IUPAC Name
1,2-dibromo-3-chloropropane
CAS Registry Number 67708-83-2
SMILES
ClCC(Br)CBr
InChI Identifier
InChI=1S/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2
InChI Key InChIKey=WBEJYOJJBDISQU-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Halides
Class Organochlorides
Sub Class Alkyl Chlorides
Direct Parent Alkyl Chlorides
Alternative Parents
  • Alkyl Bromides
Molecular Framework Aliphatic Acyclic Compounds
Substituents Not Available
External Descriptors Not Available
DrugBank ID Not Available
PubChem Compound ID 7280 Link_out
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
CTD ID Not Available
Stitch ID Dibromochloropropane Link_out
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link Not Available
Physical Properties
Appearance Colorless liquid.
Melting Point Not Available
Solubility Not Available
Predicted LogP 2.5957520706666664
Toxicity Profile
Route of Exposure Oral (R236) ; inhalation (R236) ; dermal (R236)
Mechanism of Action The initial metabolism of dibromochloropropane to reactive epoxide metabolites that bind to DNA and other macromolecules may be responsible for its hepatotoxicity and nephrotoxicity. The mechanism of dibromochloropropane's testicular toxicity is believed to be due to either the inhibition of sperm carbohydrate metabolism, probably at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain, or direct DNA damage caused by its metabolites. (R236, R043)
Metabolism Dibromochloropropane is absorbed via oral, inhalation, and dermal routes. It accumulates mainly in the kidney, liver, and adipose tissues. Dibromochloropropane is initially converted to epoxy derivatives, which are further hydrolyzed and debrominated. Glutathione (GSH) conjugation of epoxide intermediates in the liver is believed to produce precursors to toxic intermediates. The metabolites are excreted mainly in the urine. (R236)
Toxicity Values LD50: 100 mg/kg (Oral, Rabbit) (R292) LC50: 1480 mg/m3 over 1 hour (Inhalation, Rat) (R292)
Lethal Dose Not Available
Carcinogenicity (IARC Classification) 2B, possibly carcinogenic to humans. (R264)
Uses/Sources Dibromochloropropane is the active ingredient in the nematicide Nemagon, also known as Fumazone. Nemagon is a soil fumigant formerly used in agriculture. (R236)
Minimum Risk Level Intermediate Inhalation: 0.0002 ppm (R260) Intermediate Oral: 0.002 mg/kg/day (R260)
Health Effects Breathing high levels of dibromochloropropane causes reproductive damage, including reduced sperm counts, birth defects, and infertility. It may also damage the stomach, liver, kidneys, brain, spleen, blood, and lungs, and cause skin and eye damage from direct contact. (R236)
Symptoms Symptoms of dibromochloropropane exposure include headaches, nausea, lightheadedness, and weakness. (R236)
Treatment Not Available
References
General References
  • R237 — Wikipedia. 1,2-Dibromo-3-chloropropane. Last Updated 25 April 2009. [Link]
  • R236 — ATSDR - Agency for Toxic Substances and Disease Registry (1992). Toxicological profile for 1,2-dibromo-3-chloropropane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  • R292 — USEPA (1985). Drinking Water Criteria Document (Draft) 1,2-Dibromo-3-chloropropane.
  • R264 — International Agency for Research on Cancer (2009). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  • R260 — ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

Targets

1. NADH-ubiquinone oxidoreductase chain 1

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03886 Link_out
Gene: MT-ND1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

2. NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P49821 Link_out
Gene: NDUFV1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

3. NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P19404 Link_out
Gene: NDUFV2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

4. NADH dehydrogenase [ubiquinone] flavoprotein 3, mitochondrial

Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone.

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P56181 Link_out
Gene: NDUFV3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

5. NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O75306 Link_out
Gene: NDUFS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

6. NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O75489 Link_out
Gene: NDUFS3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

7. NADH dehydrogenase [ubiquinone] iron-sulfur protein 4, mitochondrial

Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone.

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O43181 Link_out
Gene: NDUFS4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

8. NADH dehydrogenase [ubiquinone] iron-sulfur protein 5

Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone.

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O43920 Link_out
Gene: NDUFS5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

9. NADH dehydrogenase [ubiquinone] iron-sulfur protein 6, mitochondrial

Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone.

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O75380 Link_out
Gene: NDUFS6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

10. NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O75251 Link_out
Gene: NDUFS7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

11. NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). May donate electrons to ubiquinone.

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: O00217 Link_out
Gene: NDUFS8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

12. NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). This is the largest subunit of complex I and it is a component of the iron-sulfur (IP) fragment of the enzyme. It may form part of the active site crevice where NADH is oxidized.

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P28331 Link_out
Gene: NDUFS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

13. NADH-ubiquinone oxidoreductase chain 2

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03891 Link_out
Gene: MT-ND2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

14. NADH-ubiquinone oxidoreductase chain 3

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03897 Link_out
Gene: MT-ND3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

15. NADH-ubiquinone oxidoreductase chain 4

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03905 Link_out
Gene: MT-ND4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

16. NADH-ubiquinone oxidoreductase chain 4L

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03901 Link_out
Gene: MT-ND4L Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

17. NADH-ubiquinone oxidoreductase chain 5

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03915 Link_out
Gene: MT-ND5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

18. NADH-ubiquinone oxidoreductase chain 6

Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).

Inhibition of sperm carbohydrate metabolism at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain is a factor of 1,2-dibromo-3-chloropropane's testicular toxicity. (R238)
UniProt ID: P03923 Link_out
Gene: MT-ND6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R043 — Greenwell A, Tomaszewski KE, Melnick RL: A biochemical basis for 1,2-dibromo-3-chloropropane-induced male infertility: inhibition of sperm mitochondrial electron transport activity. Toxicol Appl Pharmacol. 1987 Nov;91(2):274-80. [3672526 Link_out]

19. Estrogen receptor

Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Isoform 3 can bind to ERE and inhibit isoform 1.

Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (S301)
UniProt ID: P03372 Link_out
Gene: ESR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • S301 — Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors ? and ?: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.

20. Estrogen receptor beta

Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.

Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (S301)
UniProt ID: Q92731 Link_out
Gene: ESR2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • S301 — Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors ? and ?: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.