Page last updated: 2024-10-24
hydroxyphenylpyruvate reductase activity
Definition
Target type: molecularfunction
Catalysis of the reaction: 3-(4-hydroxyphenyl)lactate + NAD+ = 3-(4-hydroxyphenyl)pyruvate + NADH. [EC:1.1.1.237, MetaCyc:HYDROXYPHENYLPYRUVATE-REDUCTASE-RXN, RHEA:10780]
Hydroxyphenylpyruvate reductase (HPPR) is an enzyme that catalyzes the NADPH-dependent reduction of 4-hydroxyphenylpyruvate (HPP) to homogentisate. This reaction is a key step in the tyrosine catabolic pathway, which breaks down tyrosine into fumarate and acetoacetate. HPP is a toxic compound that can accumulate in the body if HPPR activity is deficient. HPPR is a homodimeric protein with a molecular weight of approximately 80 kDa. Each subunit contains a tightly bound NADPH molecule and a flavin adenine dinucleotide (FAD) cofactor. The active site of HPPR is located in a cleft between the two subunits. The mechanism of HPPR catalysis involves the following steps: 1) Binding of HPP and NADPH to the active site. 2) Reduction of FAD by NADPH. 3) Transfer of electrons from reduced FAD to HPP, resulting in the formation of homogentisate. 4) Release of homogentisate and NADP+ from the active site. HPPR is a highly specific enzyme that is only active with HPP as a substrate. It is also highly regulated, with its activity being influenced by factors such as substrate concentration, pH, and temperature. Mutations in the HPPR gene can lead to a variety of disorders, including alkaptonuria, a rare metabolic disorder characterized by the accumulation of homogentisate in the urine and tissues. HPPR is also involved in the biosynthesis of some secondary metabolites, such as melanin and lignin.'
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Proteins (1)
| Protein | Definition | Taxonomy |
|---|---|---|
| Malate dehydrogenase, cytoplasmic | A malate dehydrogenase, cytoplasmic that is encoded in the genome of human. [PRO:DNx, UniProtKB:P40925] | Homo sapiens (human) |
Compounds (12)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| benzyl benzoate | benzyl benzoate : A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia. benzyl benzoate: structure; acarosan, a moist powder composed of wetted cellulose and benzyl benzoate, is used on carpets as an acaricide | benzoate ester; benzyl ester | acaricide; plant metabolite; scabicide |
| clotrimazole | conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes | antiinfective agent; environmental contaminant; xenobiotic | |
| econazole | 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group. econazole : A racemate composed of equimolar amounts of (R)- and (S)-econazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. Econazole: An imidazole derivative that is commonly used as a topical antifungal agent. | dichlorobenzene; ether; imidazoles; monochlorobenzenes | |
| fluconazole | fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis. Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS. | conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug | environmental contaminant; P450 inhibitor; xenobiotic |
| glyburide | glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group. Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide | monochlorobenzenes; N-sulfonylurea | anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent |
| ketoconazole | 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively. | dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine | |
| mefenamic acid | mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis. Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. | aminobenzoic acid; secondary amino compound | analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic |
| miconazole | 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes. Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion. | dichlorobenzene; ether; imidazoles | |
| nicardipine | 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents. | benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound | |
| oxaprozin | oxaprozin : A monocarboxylic acid that is a propionic acid derivative having a 4,5-diphenyl-1,3-oxazol-2-yl substituent at position 3. It is non-steroidal anti-inflammatory drug commonly used to relieve the pain and inflammatory responses associated with osteoarthritis and rheumatoid arthritis. Oxaprozin: An oxazole-propionic acid derivative, cyclooxygenase inhibitor, and non-steroidal anti-inflammatory drug that is used in the treatment of pain and inflammation associated with of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; and ARTHRITIS, JUVENILE. | 1,3-oxazoles; monocarboxylic acid | analgesic; non-steroidal anti-inflammatory drug |
| sulconazole | 1-{2-[(4-chlorobenzyl)sulfanyl]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole : A member of the class of imidazoles that is 1-ethyl-1H-imidazole in which one of the hydrogens of the methyl group is replaced by a (4-chlorobenzyl)sulfanediyl group while a second is replaced by a 2,4-dichlorophenyl group. sulconazole : A racemate comprising equimolar amounts of (R)- and (S)-sulconazole. An antifungal agent with activity against Candida species, it is used (generally as the nitrate salt) for the topical treatment of fungal skin infections. sulconazole: RN given refers to cpd with unspecified isomeric designation; structure given in first source | dichlorobenzene; imidazoles; monochlorobenzenes; organic sulfide | |
| delavirdine | delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection. Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. | aminopyridine; indolecarboxamide; N-acylpiperazine; sulfonamide | antiviral drug; HIV-1 reverse transcriptase inhibitor |