Page last updated: 2024-10-24

halogenated hydrocarbon metabolic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways involving halogenated hydrocarbons, compounds derived from hydrocarbons by replacing one or more hydrogen atoms with halogen atoms. Halogens include fluorine, chlorine, bromine and iodine. [GOC:ai, GOC:krc]

Halogenated hydrocarbon metabolic process involves the enzymatic transformation of organic compounds containing halogens (fluorine, chlorine, bromine, or iodine). This process is crucial for the biodegradation and detoxification of various halogenated hydrocarbons that can be found in the environment, including industrial byproducts, pesticides, and pollutants. The enzymes responsible for these reactions vary depending on the specific halogen and the structure of the hydrocarbon.

**Key Steps in Halogenated Hydrocarbon Metabolism:**

* **Hydroxylation:** Initial oxidation of the hydrocarbon molecule by enzymes like cytochrome P450 monooxygenases, introducing a hydroxyl group. This step increases the molecule's polarity, making it more susceptible to further degradation.
* **Dehalogenation:** Removal of halogen atoms from the molecule, which can occur through various enzymatic reactions, including reductive dehalogenation and oxidative dehalogenation.
* **Conjugation:** Attachment of polar functional groups, such as glucuronic acid or glutathione, to the halogenated compound, further increasing its water solubility and promoting its excretion.

**Examples of Halogenated Hydrocarbon Metabolic Pathways:**

* **Metabolism of Chlorinated Aliphatics:** Compounds like trichloroethylene and tetrachloroethylene undergo hydroxylation and dehalogenation reactions, ultimately leading to their conversion to less toxic products.
* **Metabolism of Chlorinated Aromatics:** Compounds like polychlorinated biphenyls (PCBs) are metabolized through a series of oxidation and dechlorination reactions, resulting in the production of water-soluble metabolites that can be excreted.
* **Metabolism of Brominated Flame Retardants:** Compounds like polybrominated diphenyl ethers (PBDEs) are subject to hydroxylation, dehalogenation, and conjugation reactions, aiming to reduce their toxicity and facilitate their elimination from the body.

**Significance:**

* **Environmental Remediation:** Microorganisms with the ability to degrade halogenated hydrocarbons play a vital role in cleaning up contaminated environments.
* **Human Health:** Understanding halogenated hydrocarbon metabolism is crucial for assessing their toxicological effects and developing strategies to mitigate their potential health risks.
* **Industrial Applications:** Metabolic pathways involving halogenated hydrocarbons are utilized in various industrial processes, such as the production of pharmaceuticals and agricultural chemicals.
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Proteins (2)

ProteinDefinitionTaxonomy
Cytochrome P450 2E1A cytochrome P450 2E1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P05181]Homo sapiens (human)
Cytochrome P450 2E1A cytochrome P450 2E1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P05181]Homo sapiens (human)

Compounds (25)

CompoundDefinitionClassesRoles
tacrinetacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.

Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.
acridines;
aromatic amine
EC 3.1.1.7 (acetylcholinesterase) inhibitor
carbon tetrachlorideCarbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed)

tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.
chlorocarbon;
chloromethanes
hepatotoxic agent;
refrigerant
3-hydroxyacetanilidemetacetamol : A derivative of phenol which has an acetamido substituent located meta to the phenolic -OH group. It is a non-toxic regioisomer of paracetamol with analgesic properties, but has never been marketed as a drug.acetamides;
phenols
non-narcotic analgesic
phenethyl isothiocyanatephenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.

phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma
isothiocyanateantineoplastic agent;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
metabolite
tranylcypromine(1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.

tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).

Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311)
2-phenylcyclopropan-1-amine
proadifen hydrochloride
pirlindolepirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812carbazoles
hexyl nicotinate
6-paradol6-paradol: induces apoptosis; structure in first sourceketone;
monomethoxybenzene;
phenols
cp-55,940
gefitinibaromatic ether;
monochlorobenzenes;
monofluorobenzenes;
morpholines;
quinazolines;
secondary amino compound;
tertiary amino compound
antineoplastic agent;
epidermal growth factor receptor antagonist
oky 0251-carboxyheptylimidazole: RN given refers to parent cpd
tariquidarbenzamides
(3r)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanoneWIN 55212-2 : A organic heterotricyclic compound that is 5-methyl-3-(morpholin-4-ylmethyl)-2,3-dihydro[1,4]oxazino[2,3,4-hi]indole substituted at position 6 by a 1-naphthylcarbonyl group.morpholines;
naphthyl ketone;
organic heterotricyclic compound;
synthetic cannabinoid
analgesic;
apoptosis inhibitor;
neuroprotective agent
bergamottinbergamottin: constituent of bergamot oil; structure given in first sourcefuranocoumarinmetabolite
pai 039tiplaxtinin: inhibitor of plasminogen activator inhibitor-1indole-3-acetic acids
orteronelorteronel: non-steroidal 17,20-lyase inhibitor; structure in first source
CB-13naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: has antihyperalgesic activity; structure in first sourcebenzophenones
bibw 2992aromatic ether;
enamide;
furans;
monochlorobenzenes;
organofluorine compound;
quinazolines;
secondary carboxamide;
tertiary amino compound
antineoplastic agent;
tyrosine kinase inhibitor
vx-770ivacaftor : An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.

ivacaftor: a CFTR potentiator; structure in first source
aromatic amide;
monocarboxylic acid amide;
phenols;
quinolone
CFTR potentiator;
orphan drug
cct 128930
e-52862
glpg0634
kaf156ganaplacide: antimalarial
(5s,6s,9r)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5h-cyclohepta(b)pyridin-9-yl 4-(2-oxo-2,3-dihydro-1h-imidazo(4,5-b)pyridin-1-yl)piperidine-1-carboxylate