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biphenyl metabolic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways involving biphenyl, a toxic aromatic hydrocarbon used as a heat transfer agent, as a fungistat in packaging citrus fruits and in plant disease control. Biphenyl can be chlorinated with 1-10 chlorine molecules to form polychlorinated biphenyls (PCBs). [GOC:jl]

The biphenyl metabolic process involves the breakdown of biphenyl, a complex aromatic hydrocarbon, by living organisms. It's a crucial process in the biodegradation of this environmental contaminant, as biphenyl can accumulate in the environment and pose potential health risks. Here's a detailed breakdown of the process:

1. **Initial Oxidation:** The first step involves the oxidation of biphenyl, usually catalyzed by enzymes called dioxygenases. These enzymes add oxygen atoms to the molecule, leading to the formation of dihydrodiol metabolites.

2. **Dehydration and Aromatization:** The dihydrodiol intermediates undergo dehydration and aromatization, forming hydroxylated biphenyls. This process eliminates water molecules and restores the aromatic ring structure.

3. **Further Oxidation:** The hydroxylated biphenyls can be further oxidized by various enzymes, including monooxygenases and dehydrogenases. This results in the formation of various metabolites with different functional groups, such as ketones, aldehydes, and carboxylic acids.

4. **Ring Cleavage:** Some metabolites undergo ring cleavage reactions, where the aromatic rings are broken down into smaller, more readily degradable molecules. This step is often catalyzed by enzymes like dioxygenases and dioxygenases.

5. **Final Degradation:** The final products of biphenyl metabolism are typically simple organic compounds, such as carbon dioxide, water, and organic acids. These compounds can be readily assimilated by organisms or released into the environment.

The specific enzymes and pathways involved in biphenyl metabolism vary depending on the organism involved. Bacteria, fungi, and certain plants have evolved sophisticated metabolic pathways for degrading biphenyl, playing a vital role in the bioremediation of contaminated environments.'
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Proteins (2)

ProteinDefinitionTaxonomy
3-oxo-5-alpha-steroid 4-dehydrogenase 2A 3-oxo-5-alpha-steroid 4-dehydrogenase 2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P31213]Homo sapiens (human)
Cytochrome P450 4B1A cytochrome P450 4B1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P13584]Homo sapiens (human)

Compounds (14)

CompoundDefinitionClassesRoles
prazosinprazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.

Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.
aromatic ether;
furans;
monocarboxylic acid amide;
piperazines;
quinazolines
alpha-adrenergic antagonist;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
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
finasteridefinasteride : An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.

Finasteride: An orally active 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE inhibitor. It is used as a surgical alternative for treatment of benign PROSTATIC HYPERPLASIA.
3-oxo steroid;
aza-steroid;
delta-lactam
androgen antagonist;
antihyperplasia drug;
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
proadifen hydrochloride
turosterideturosteride: a 5alpha-reductase inhibitor; structure given in first source; RN given refers to the (5alpha,17beta)-isomer
sertralinesertraline : A member of the class of tetralins that is tetralin which is substituted at positions 1 and 4 by a methylamino and a 3,4-dichlorophenyl group, respectively (the S,S diastereoisomer). A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as the hydrochloride salt as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.

Sertraline: A selective serotonin uptake inhibitor that is used in the treatment of depression.
dichlorobenzene;
secondary amino compound;
tetralins
antidepressant;
serotonin uptake inhibitor
epristerideepristeride: structure given in first sourcesteroid acid
pirlindolepirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812carbazoles
indole-2-carboxylic acidindolyl carboxylic acid
fce 28260(22RS-N-1,1,1-trifluoro-2-phenylprop-2-yl)-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide: structure given in first source
ly 300502
17-n,n-diethylcarbamoyl-4-methyl-4-azaandrostane-3-one17-N,N-diethylcarbamoyl-4-methyl-4-azaandrostane-3-one: inhibitor of testosterone 5-alpha reductase, receptor binding & nuclear uptake of androgens in the prostate
dutasteridedutasteride : An aza-steroid that is inasteride in which the tert-butyl group is replaced by a 2,5-bis(trifluoromethyl)phenyl group. A synthetic 4-azasteroid, dutasteride is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5alpha-reductase, an intracellular enzyme that converts testosterone to 5alpha-dihydrotestosterone. Dutasteride is used for the treatment of symptomatic benign prostatic hyperplasia in men with an enlarged prostate gland.

Dutasteride: A 5-ALPHA-REDUCTASE INHIBITOR that is reported to inhibit both type-1 and type2 isoforms of the enzyme and is used to treat BENIGN PROSTATIC HYPERPLASIA.
(trifluoromethyl)benzenes;
aza-steroid;
delta-lactam
antihyperplasia drug;
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
kaf156ganaplacide: antimalarial