Target type: biologicalprocess
The chemical reactions and pathways involving guanine, 2-amino-6-hydroxypurine, a purine that is one of the five main bases found in nucleic acids and a component of a number of phosphorylated guanosine derivatives whose metabolic or regulatory functions are important. [GOC:go_curators]
Guanine metabolism is a complex and essential biological process that involves the synthesis, degradation, and interconversion of guanine, a purine base. This process is crucial for the production of DNA, RNA, and other essential biomolecules.
**Guanine Synthesis:**
1. **De novo purine biosynthesis:** Guanine is synthesized from simpler precursors, such as amino acids and tetrahydrofolate, through a series of enzymatic reactions.
2. **Salvage pathway:** Guanine can also be recycled from existing purine bases, such as hypoxanthine and xanthine.
**Guanine Degradation:**
1. **Guanine deaminase:** Guanine is deaminated to xanthine by the enzyme guanine deaminase.
2. **Xanthine oxidase:** Xanthine is further oxidized to uric acid by xanthine oxidase.
3. **Uric acid excretion:** Uric acid is the final product of purine degradation in humans and is excreted in the urine.
**Interconversion of Guanine with Other Purines:**
1. **Hypoxanthine-guanine phosphoribosyltransferase (HGPRT):** This enzyme catalyzes the conversion of hypoxanthine to inosine monophosphate (IMP) and guanine to guanosine monophosphate (GMP).
2. **GMP synthetase:** This enzyme converts IMP to GMP, using glutamine as an amino group donor.
**Regulation of Guanine Metabolism:**
Guanine metabolism is tightly regulated to maintain appropriate levels of purine nucleotides.
1. **Feedback inhibition:** The synthesis of purine nucleotides is inhibited by high concentrations of these nucleotides.
2. **Hormonal regulation:** Hormones such as insulin and growth hormone can stimulate purine synthesis.
3. **Dietary intake:** The intake of purine-rich foods can affect purine metabolism.
**Disorders of Guanine Metabolism:**
Defects in guanine metabolism can lead to various diseases, including:
1. **Lesch-Nyhan syndrome:** A rare X-linked recessive disorder caused by a deficiency in HGPRT, leading to hyperuricemia, neurological abnormalities, and self-mutilation.
2. **Gout:** A metabolic disorder characterized by the accumulation of uric acid in the joints, leading to inflammation and pain.
**Clinical Significance:**
The understanding of guanine metabolism is critical for the diagnosis and treatment of various diseases.
1. **Diagnosis:** Measuring purine metabolites in blood and urine can be used to diagnose disorders of guanine metabolism.
2. **Treatment:** The treatment of these disorders may involve dietary modifications, medications to inhibit purine synthesis or uric acid production, or enzyme replacement therapy.'
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| Protein | Definition | Taxonomy |
|---|---|---|
| Guanine deaminase | A guanine deaminase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9Y2T3] | Homo sapiens (human) |
| Lysine-specific histone demethylase 1A | A lysine-specific histone demethylase 1A that is encoded in the genome of human. [PRO:DNx, UniProtKB:O60341] | Homo sapiens (human) |
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| uric acid | 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8. uric acid : An oxopurine that is the final oxidation product of purine metabolism. Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN. | uric acid | Escherichia coli metabolite; human metabolite; mouse metabolite |
| xanthine | 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. | xanthine | Saccharomyces cerevisiae metabolite |
| berberine | alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound | antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker | |
| caffeine | purine alkaloid; trimethylxanthine | adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic | |
| phenelzine | Phenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC. | primary amine | |
| raloxifene | raloxifene : A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogens at positions 2, 3, and 6 have been replaced by p-hydroxyphenyl, p-[2-(piperidin-1-yl)ethoxy]benzoyl, and hydroxy groups, respectively. | 1-benzothiophenes; aromatic ketone; N-oxyethylpiperidine; phenols | bone density conservation agent; estrogen antagonist; estrogen receptor modulator |
| vorinostat | vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL). Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME. | dicarboxylic acid diamide; hydroxamic acid | antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor |
| 2-phenylcyclopropan-1-amine | 2-phenylcyclopropan-1-amine : A member of the class of cyclopropanes carrying amino and phenyl substituents at positions 1 and 2 respectively. | benzenes; cyclopropanes; primary amine | |
| aminoimidazole carboxamide | 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4. Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases. | aminoimidazole; monocarboxylic acid amide | mouse metabolite |
| hesperidin | hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. Hesperidin: A flavanone glycoside found in CITRUS fruit peels. | 3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside | mutagen |
| palmatine | burasaine: structure in first source | berberine alkaloid; organic heterotetracyclic compound | plant 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 | |
| (1S,2R)-tranylcypromine | (1S,2R)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1S,2R)-enantiomer of tranylcypromine. | 2-phenylcyclopropan-1-amine | |
| 2,6-diaminopurine | 9H-purine-2,6-diamine : A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups. | 2,6-diaminopurines; primary amino compound | antineoplastic agent |
| dehydrocorydalin | dehydrocorydalin: alkaloid from Corydalis bulbuso D.C. used in therapy of peptic ulcer; RN given refers to parent cpd | alkaloid | |
| baicalin | dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative | antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug | |
| 7-methylxanthine | oxopurine; purine alkaloid | human xenobiotic metabolite; mouse metabolite; plant metabolite | |
| hesperetin | 3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone | antineoplastic agent; antioxidant; plant metabolite | |
| columbamine | berberine alkaloid; organic heterotetracyclic compound | ||
| jatrorrhizine | jatrorrhizine: isolated from bark of Enantia chlorantha (Annonaceae); structure given in first source | alkaloid | |
| higenamine | higenamine: structure; RN given refers to (+-)-isomer | norcoclaurine | |
| tanshinone | tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent | abietane diterpenoid | anticoronaviral agent |
| azepinomycin | azepinomycin: from Streptomyces sp. MF718-03; structure given in first source; RN given from Chem Abst Index Guide 1982-6 | ||
| cryptotanshinone | cryptotanshinone: from Salvia miltiorrhiza | abietane diterpenoid | anticoronaviral agent |
| epiberberine | epiberberine: isolated in plants of Coptis from China | ||
| erlotinib | aromatic ether; quinazolines; secondary amino compound; terminal acetylenic compound | antineoplastic agent; epidermal growth factor receptor antagonist; protein kinase inhibitor | |
| resveratrol | trans-resveratrol : A resveratrol in which the double bond has E configuration. | resveratrol | antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger |
| curcumin | curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa. Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes. | aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol | anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger |
| capsaicin | ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers. | capsaicinoid | non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker |
| (1R,2S)-tranylcypromine hydrochloride | (1R,2S)-tranylcypromine hydrochloride : A hydrochloride obtained by combining (1R,2S)-tranylcypromine with one equivalent of hydrochloric acid. | hydrochloride | |
| N5-(2-chloro-6-phenoxybenzyl)-1H-1,2,4-triazole-3,5-diamine | aromatic ether | ||
| mdl 72527 | MDL 72527: RN given refers to di-HCl; RN for parent cpd not available 6/85; polyamine oxidase inhibitor | ||
| wogonoside | wogonin 7-O-beta-D-glucuronide : The glycosyloxyflavone which is the 7-O-glucuronide of wogonin. wogonoside: from Scutellaria baicalensis; structure in first source | beta-D-glucosiduronic acid; glycosyloxyflavone; monohydroxyflavone; monomethoxyflavone; monosaccharide derivative | |
| quercetin | 7-hydroxyflavonol; pentahydroxyflavone | antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger | |
| biochanin a | 4'-methoxyisoflavones; 7-hydroxyisoflavones | antineoplastic agent; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; phytoestrogen; plant metabolite; tyrosine kinase inhibitor | |
| quercetin 3-o-glucopyranoside | quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells quercetin 3-O-glucopyranoside: structure in first source | beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone | antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite |
| rutin | Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders. | disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone | antioxidant; metabolite |
| baicalein | trihydroxyflavone | angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger | |
| diosmetin | 3'-hydroxyflavonoid; monomethoxyflavone; trihydroxyflavone | angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; bone density conservation agent; cardioprotective agent; plant metabolite; tropomyosin-related kinase B receptor agonist; vasodilator agent | |
| diosmin | dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside | anti-inflammatory agent; antioxidant | |
| mangostin | alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities. mangostin: xanthone from rind of Garcinia mangostana Linn. fruit | aromatic ether; phenols; xanthones | antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite |
| wogonin | wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8. wogonin: structure in first source | dihydroxyflavone; monomethoxyflavone | angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite |
| rosmarinic acid | (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid. rosmarinic acid: RN given refers to parent cpd; promote OT project | rosmarinic acid | geroprotector; plant metabolite |
| afimoxifene | |||
| icaritin | icaritin: structure in first source | ||
| icariin | flavonols; glycosyloxyflavone | antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen | |
| baohuoside i | baohuoside I: structure given in first source; isolated from the herb Epimedium davidii | glycosyloxyflavone | anti-inflammatory agent; antineoplastic agent; apoptosis inducer; plant metabolite |
| salvianolic acid B | salvianolic acid B : A member of the class of 1-benzofurans that is an antioxidant and free radical scavenging compound extracted from S. miltiorrhiza salvianolic acid B: isolated from Salvia miltiorrhiza | 1-benzofurans; catechols; dicarboxylic acid; enoate ester; polyphenol | anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; apoptosis inducer; autophagy inhibitor; cardioprotective agent; hepatoprotective agent; hypoglycemic agent; neuroprotective agent; osteogenesis regulator; plant metabolite |
| Diosmetin 7-O-beta-D-glucopyranoside | flavonoids; glycoside | ||
| polymyxin b(1) | |||
| Dihydrotanshinone I | dihydrotanshinone I: extracted from Radix Salviae | abietane diterpenoid | anticoronaviral agent |
| N-(3-ethynylphenyl)-6,7-dimethoxy-4-quinazolinamine | quinazolines | ||
| 1-(4-methyl-1-piperazinyl)-2-[[(1R,2S)-2-(4-phenylmethoxyphenyl)cyclopropyl]amino]ethanone | amino acid amide | ||
| gsk2879552 | GSK2879552 : A member of the class of piperidines that is piperidine substituted by (4-carboxyphenyl)methyl and {[(1R,2S)-2-phenylcyclopropyl]amino}methyl groups at positions 1 and 4, respectively. It is a potent and irreversible inhibitor of lysine specific demethylase 1 (LSD1, also known as KDM1A). It was under clinical investigation for the treatment of acute myeloid leukaemia and small cell lung carcinoma. GSK2879552: inhibits lysine demethylase 1; structure in first source | benzenes; benzoic acids; cyclopropanes; monocarboxylic acid; piperidines; secondary amino compound; tertiary amino compound | antineoplastic agent; EC 1.14.99.66 (lysine-specific histone demethylase 1A) inhibitor |
| osimertinib | osimertinib : A member of the class of aminopyrimidines that is 4-(1-methylindol-3-yl)pyrimidin-2-amine in which one of the amino hydrogens is replaced by a 2-methoxy-4-[2-(dimethylamino)ethyl](methyl)amino-5-acrylamidophenyl group. Used (as the mesylate salt) for treatment of EGFR T790M mutation positive non-small cell lung cancer. osimertinib: an EGFR tyrosine kinase inhibitor | acrylamides; aminopyrimidine; biaryl; indoles; monomethoxybenzene; secondary amino compound; secondary carboxamide; substituted aniline; tertiary amino compound | antineoplastic agent; epidermal growth factor receptor antagonist |
| guanine | 2-aminopurines; oxopurine; purine nucleobase | algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite |