CHEBI:16598 - DDE

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ChEBI Name DDE
ChEBI ID CHEBI:16598
Definition A chlorophenylethylene that is ethylene substituted by two 4-chlorophenyl groups at position 1 and two chlorine atoms at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Doug Howe
Secondary ChEBI IDs CHEBI:474, CHEBI:195494, CHEBI:11130, CHEBI:18851
Supplier Information ChemicalBook:CB9776968, eMolecules:479705, ZINC000001530006
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Dichlorodiphenyldichloroethylene (DDE) is a chemical compound formed by the loss of hydrogen chloride (dehydrohalogenation) from DDT, of which it is one of the more common breakdown products. Due to DDT's massive prevalence in society and agriculture during the mid 20th century, DDT and DDE are still widely seen in animal tissue samples. DDE is particularly dangerous because it is fat-soluble like other organochlorines; thus, it is rarely excreted from the body, and concentrations tend to increase throughout life. The major exception is the excretion of DDE in breast milk, which transfers a substantial portion of the mother's DDE burden to the young animal or child. Along with accumulation over an organism's lifetime, this stability leads to bioaccumulation in the environment, which amplifies DDE's negative effects.
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Formula C14H8Cl4
Net Charge 0
Average Mass 318.020
Monoisotopic Mass 315.93801
InChI InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H
InChIKey UCNVFOCBFJOQAL-UHFFFAOYSA-N
SMILES ClC(Cl)=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1
Roles Classification
Chemical Role(s): persistent organic pollutant
Any environmental contaminant that is resistant to environmental degradation through photolytic, biological or chemical processes. Such substances can have significant impact on health and the environment, as they persist in the environment, bioaccumulate in animal tissue and so biomagnify in food chains.
Biological Role(s): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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ChEBI Ontology
Outgoing DDE (CHEBI:16598) has role human xenobiotic metabolite (CHEBI:76967)
DDE (CHEBI:16598) has role persistent organic pollutant (CHEBI:77853)
DDE (CHEBI:16598) is a chlorophenylethylene (CHEBI:23155)
DDE (CHEBI:16598) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name
1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene
Synonyms Sources
1,1'-(2,2-dichloroethene-1,1-diyl)bis(4-chlorobenzene) IUPAC
1,1-bis-(4-chlorophenyl)-2,2-dichloroethene ChEBI
1,1-dichloro-2,2-bis(4'-chlorophenyl)ethylene ChEBI
1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethylene KEGG COMPOUND
1,1-Dichloro-2,2-bis(4-chlorophenyl)ethylene KEGG COMPOUND
1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene UniProt
2,2'-bis(4-chlorophenyl)-1,1-dichloroethylene SUBMITTER
4,4'-DDE ChemIDplus
DDE KEGG COMPOUND
p,p'-(Dichlorodiphenyl)-2,2-dichloroethylene ChemIDplus
p,p'-DDE ChemIDplus
Manual Xrefs Databases
6WS PDBeChem
c0406 UM-BBD
C04596 KEGG COMPOUND
DICHLOROBIS-CPD MetaCyc
Dichlorodiphenyldichloroethylene Wikipedia
FDB097419 FooDB
HMDB0304759 HMDB
View more database links
Registry Numbers Types Sources
1913355 Reaxys Registry Number Reaxys
72-55-9 CAS Registry Number KEGG COMPOUND
72-55-9 CAS Registry Number NIST Chemistry WebBook
72-55-9 CAS Registry Number ChemIDplus
Citations
Cortés-Montoya V, Ortiz-Robles CD, Rivera-Maya OB, Palacios-Valladares JR, Ramirez-Gutierrez EF, Calderón-Aranda ES (2023)
The p,p'-DDE disturbs the M1 function without affecting the M2 phenotype nor unstimulated bone marrow-derived macrophages from BALB/c mice.
Toxicology 493, 153554 [PubMed:37236336]
[show Abstract]
Jiang J, He B, Wei Y, Cui J, Zhang Q, Liu X, Liu D, Wang P, Zhou Z (2022)
The toxic effects of combined exposure of chlorpyrifos and p, p'-DDE to zebrafish (Danio rerio) and tissue bioaccumulation.
Aquatic toxicology (Amsterdam, Netherlands) 248, 106194 [PubMed:35623197]
[show Abstract]
Li S, Shao W, Wang C, Wang L, Xia R, Yao S, Du M, Ji X, Chu H, Zhang Z, Wang M, Wang SL (2021)
Identification of common genetic variants associated with serum concentrations of p, p'-DDE in non-occupational populations in eastern China.
Environment international 152, 106507 [PubMed:33756427]
[show Abstract]
Plouffe L, Bosson-Rieutort D, Madaniyazi L, Iwai-Shimada M, Nakai K, Tatsuta N, Nakayama SF, Verner MA (2020)
Estimated postnatal p,p'-DDT and p,p'-DDE levels and body mass index at 42 months of age in a longitudinal study of Japanese children.
Environmental health : a global access science source 19, 49 [PubMed:32393266]
[show Abstract]
Jugan J, Lind P, Salihovic S, Stubleski J, Kärrman A, Lind L, Merrill M (2020)
SUN-571 The Associations Between p,p’-DDE Levels and Serum Levels of Lipoproteins and Their Subclasses in an Elderly Population Determined by Lipidomics Analysis
Journal of the Endocrine Society 4, [PubMed Central:PMC7208238]
[show Abstract]
Jugan J, Lind PM, Salihovic S, Stubleski J, Kärrman A, Lind L, La Merrill MA (2020)
The associations between p,p'-DDE levels and plasma levels of lipoproteins and their subclasses in an elderly population determined by analysis of lipoprotein content.
Lipids in health and disease 19, 249 [PubMed:33287856]
[show Abstract]
Pavlíková N, Daniel P, Šrámek J, Jelínek M, Šrámková V, Němcová V, Balušíková K, Halada P, Kovář J (2019)
Upregulation of vitamin D-binding protein is associated with changes in insulin production in pancreatic beta-cells exposed to p,p'-DDT and p,p'-DDE.
Scientific reports 9, 18026 [PubMed:31792309]
[show Abstract]
Nwachukwu JC, Srinivasan S, Bruno NE, Nowak J, Wright NJ, Minutolo F, Rangarajan ES, Izard T, Yao XQ, Grant BJ, Kojetin DJ, Elemento O, Katzenellenbogen JA, Nettles KW (2017)
Systems Structural Biology Analysis of Ligand Effects on ERα Predicts Cellular Response to Environmental Estrogens and Anti-hormone Therapies.
Cell chemical biology 24, 35-45 [PubMed:28042045]
[show Abstract]
Pérez-Maldonado IN, Trejo-Acevedo A, Orta-García ST, Ochoa-Martinez AC, Varela-Silva JA, Pérez-Vázquez FJ (2014)
DDT and DDE concentrations in the blood of Mexican children residing in the southeastern region of Mexico.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 49, 87-93 [PubMed:24328540]
[show Abstract]
Nguyen PA, Trinh TH, Fukumitsu Y, Shimodaira J, Miyauchi K, Tokuda M, Kasai D, Masai E, Fukuda M (2013)
Gene cluster and regulation system for 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene (DDE) degradation in Janibacter sp. TYM3221.
Journal of bioscience and bioengineering 116, 91-100 [PubMed:23415487]
[show Abstract]
Nguyen AT, Sato Y, Iwasaki T, Miyauchi K, Tokuda M, Kasai D, Masai E, Fukuda M (2011)
Characterization of the 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene (DDE) degradation system in Janibacter sp. TYM3221.
Enzyme and microbial technology 49, 532-539 [PubMed:22142728]
[show Abstract]
Tiedeken JA, Ramsdell JS (2010)
Zebrafish seizure model identifies p,p -DDE as the dominant contaminant of fetal California sea lions that accounts for synergistic activity with domoic acid.
Environmental health perspectives 118, 545-551 (Source: SUBMITTER) [PubMed:20368122]
[show Abstract]
Shabbir A, DiStasio S, Zhao J, Cardozo CP, Wolff MS, Caplan AJ (2005)
Differential effects of the organochlorine pesticide DDT and its metabolite p,p'-DDE on p-glycoprotein activity and expression.
Toxicology and applied pharmacology 203, 91-98 [PubMed:15710169]
[show Abstract]
Younglai EV, Holloway AC, Lim GE, Foster WG (2004)
Synergistic effects between FSH and 1,1-dichloro-2,2-bis(P-chlorophenyl)ethylene (P,P'-DDE) on human granulosa cell aromatase activity.
Human reproduction (Oxford, England) 19, 1089-1093 [PubMed:15070871]
[show Abstract]
Smeds A, Saukko P (2001)
Identification and quantification of polychlorinated biphenyls and some endocrine disrupting pesticides in human adipose tissue from Finland.
Chemosphere 44, 1463-1471 [PubMed:11513126]
[show Abstract]
Last Modified
04 August 2023