cis-Chlordane (T3D0059)
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2009-03-06 18:58:00 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2014-12-24 20:21:00 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Accession Number | T3D0059 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common Name | cis-Chlordane | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Small Molecule | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | cis-Chlordane, also known as alpha-chlordane, is one of two isomers of chlordane. Chlordane is a manufactured chemical that was used as a pesticide in the United States from 1948 to 1988. (9) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Compound Type |
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| Chemical Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| 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 | InChIKey=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 |
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| Molecular Framework | Aliphatic homopolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Status | Detected and Not Quantified | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Origin | Exogenous | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Biofluid Locations | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Tissue Locations | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Pathways |
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| Applications | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Roles | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Roles | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Liquid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Appearance | Colorless to amber liquid. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra |
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| Toxicity Profile | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Route of Exposure | Oral (5) ; inhalation (5) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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. (10, 1, 2, 3, 4) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolism | Chlordane is highly lipophilic and is thus easily absorbed by ingestion, inhalation, and dermal exposure, then stored mainly in the fat. Chlordane is metabolized mainly in the liver and kidney. Metabolism is slow, and is believed to occur by multiple pathways involving cytochrome P-450 enzymes, glutathione-S-transferase type enzymes, and microsomal mixed-function oxidase systems. The metabolites are generally less toxic and include chlordene chlorohydrin, monohydroxylated dihydrochlordene, and oxychlordane. They are excreted in the urine and faeces. (10) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Toxicity Values | LD50: 200 mg/kg (Oral, Rat) (6) LD50: 343 mg/kg (Intraperitoneal, Rat) (6) LD50: 10 mg/kg (Intravenous, Mouse) (7) LD50: 780 mg/kg (Dermal, Rat) (7) LC50: 100 mg/m3 over 4 hours (Inhalation, Cat) (7) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Lethal Dose | 100 mg/kg for an adult human. (8) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Carcinogenicity (IARC Classification) | Chlordane is possibly carcinogenic to humans (Group 2B). (12) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Uses/Sources | Chlordane was used as a pesticide. (9) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Minimum Risk Level | Intermediate Inhalation: 0.0002 mg/m3 (11) Chronic Inhalation: 0.00002 mg/m3 (11) Acute Oral: 0.001 mg/kg/day (11) Intermediate Oral: 0.0006 mg/kg/day (11) Chronic Oral: 0.0006 mg/kg/day (11) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Health Effects | Chlordane is a central nervous system stimulant, and can also damage the digestive system and the liver. Large doses have been known to cause convulsions, respiratory failure, and death. Chlordane is also known to have adverse reproductive and developmental effects. (10) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Symptoms | Ingestion and inhalation of chlordane cause headaches, irritability, confusion, weakness, vision problems, vomiting, stomach cramps, diarrhea, and jaundice. (10) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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. (13) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| HMDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound ID | 12303021 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEMBL ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChemSpider ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| UniProt ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| OMIM ID | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 39068 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CTD ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Stitch ID | Chlordane, cis- | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ACToR ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| MSDS | T3D0059.pdf | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| General References |
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| Gene Regulation | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Up-Regulated Genes | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Down-Regulated Genes | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Nims RW, Lubet RA: Induction of cytochrome P-450 in the Norway rat, Rattus norvegicus, following exposure to potential environmental contaminants. J Toxicol Environ Health. 1995 Nov;46(3):271-92. [7473857 ]
- ATSDR - Agency for Toxic Substances and Disease Registry (1994). Toxicological profile for chlordane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Nims RW, Lubet RA: Induction of cytochrome P-450 in the Norway rat, Rattus norvegicus, following exposure to potential environmental contaminants. J Toxicol Environ Health. 1995 Nov;46(3):271-92. [7473857 ]
- ATSDR - Agency for Toxic Substances and Disease Registry (1994). Toxicological profile for chlordane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- General Function:
- Monooxygenase activity
- Specific Function:
- Exhibits low testosterone 6-beta-hydroxylase activity.
- Gene Name:
- CYP3A43
- Uniprot ID:
- Q9HB55
- Molecular Weight:
- 57669.21 Da
References
- Nims RW, Lubet RA: Induction of cytochrome P-450 in the Norway rat, Rattus norvegicus, following exposure to potential environmental contaminants. J Toxicol Environ Health. 1995 Nov;46(3):271-92. [7473857 ]
- ATSDR - Agency for Toxic Substances and Disease Registry (1994). Toxicological profile for chlordane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- General Function:
- Oxygen binding
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP3A5
- Uniprot ID:
- P20815
- Molecular Weight:
- 57108.065 Da
References
- Nims RW, Lubet RA: Induction of cytochrome P-450 in the Norway rat, Rattus norvegicus, following exposure to potential environmental contaminants. J Toxicol Environ Health. 1995 Nov;46(3):271-92. [7473857 ]
- ATSDR - Agency for Toxic Substances and Disease Registry (1994). Toxicological profile for chlordane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- General Function:
- Oxygen binding
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP3A7
- Uniprot ID:
- P24462
- Molecular Weight:
- 57525.03 Da
References
- Nims RW, Lubet RA: Induction of cytochrome P-450 in the Norway rat, Rattus norvegicus, following exposure to potential environmental contaminants. J Toxicol Environ Health. 1995 Nov;46(3):271-92. [7473857 ]
- ATSDR - Agency for Toxic Substances and Disease Registry (1994). Toxicological profile for chlordane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- General Function:
- Zinc ion binding
- Specific Function:
- 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. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
- General Function:
- Zinc ion binding
- Specific Function:
- 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 (PubMed:20074560). 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.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
- General Function:
- Pyrophosphatase activity
- Specific Function:
- This isozyme may play a role in skeletal mineralization.
- Gene Name:
- ALPL
- Uniprot ID:
- P05186
- Molecular Weight:
- 57304.435 Da
References
- Chatterjee K, Banerjee SK, Tiwari R, Mazumdar K, Bhattacharyya A, Chatterjee GC: Studies on the protective effects of L-ascorbic acid in chronic chlordane toxicity. Int J Vitam Nutr Res. 1981;51(3):254-65. [7319725 ]
9. DNA
- General Function:
- Used for biological information storage.
- Specific Function:
- DNA contains the instructions needed for an organism to develop, survive and reproduce.
- Molecular Weight:
- 2.15 x 1012 Da
References
- ATSDR - Agency for Toxic Substances and Disease Registry (1994). Toxicological profile for chlordane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- General Function:
- Zinc ion binding
- Specific Function:
- Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRG
- Uniprot ID:
- P62508
- Molecular Weight:
- 51305.485 Da
References
- Ariazi EA, Jordan VC: Estrogen-related receptors as emerging targets in cancer and metabolic disorders. Curr Top Med Chem. 2006;6(3):203-15. [16515477 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of hormone ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function.
- Gene Name:
- RARB
- Uniprot ID:
- P10826
- Molecular Weight:
- 50488.63 Da
References
- Lemaire G, Balaguer P, Michel S, Rahmani R: Activation of retinoic acid receptor-dependent transcription by organochlorine pesticides. Toxicol Appl Pharmacol. 2005 Jan 1;202(1):38-49. [15589975 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity).
- Gene Name:
- RARG
- Uniprot ID:
- P13631
- Molecular Weight:
- 50341.405 Da
References
- Lemaire G, Balaguer P, Michel S, Rahmani R: Activation of retinoic acid receptor-dependent transcription by organochlorine pesticides. Toxicol Appl Pharmacol. 2005 Jan 1;202(1):38-49. [15589975 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRA
- Uniprot ID:
- P11474
- Molecular Weight:
- 45509.11 Da
References
- Ariazi EA, Jordan VC: Estrogen-related receptors as emerging targets in cancer and metabolic disorders. Curr Top Med Chem. 2006;6(3):203-15. [16515477 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor, may regulate ESR1 transcriptional activity. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRB
- Uniprot ID:
- O95718
- Molecular Weight:
- 56207.085 Da
References
- Ariazi EA, Jordan VC: Estrogen-related receptors as emerging targets in cancer and metabolic disorders. Curr Top Med Chem. 2006;6(3):203-15. [16515477 ]