Classification Term: 703
6-aminopurines (ontology term: CHEMONTID:0002987)
Purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring." []
found 47 associated metabolites at category metabolite taxonomy ontology rank level.
Ancestor: Purines and purine derivatives
Child Taxonomies: 6-alkylaminopurines
Adenine
Adenine is the parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. It has a role as a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase and a member of 6-aminopurines. It derives from a hydride of a 9H-purine. A purine base and a fundamental unit of adenine nucleotides. Adenine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenine is a natural product found in Fritillaria cirrhosa, Annona purpurea, and other organisms with data available. Adenine is a purine nucleobase with an amine group attached to the carbon at position 6. Adenine is the precursor for adenosine and deoxyadenosine nucleosides. Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (A3372, A3373). Adenine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine base and a fundamental unit of ADENINE NUCLEOTIDES. See also: adenine; dextrose, unspecified form (component of) ... View More ... Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339). Widespread throughout animal and plant tissue, purine components of DNA, RNA, and coenzymes. Vitamin The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. Adenine (/ˈædɪnɪn/) (symbol A or Ade) is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA.[2] The shape of adenine is complementary to either thymine in DNA or uracil in RNA. The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an adenine residue, as part of a larger molecule. Adenosine is adenine reacted with ribose, as used in RNA and ATP; Deoxyadenosine is adenine attached to deoxyribose, as used to form DNA. Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.[3][4] Purine metabolism involves the formation of adenine and guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which in turn is synthesized from a pre-existing ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as the coenzyme tetrahydrofolate. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3].
2-Hydroxyadenine
2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50) [HMDB] 2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50). Isoguanine is an oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group.
1-Methyladenine
1-Methyladenine is the product of reaction between 1-methyladenosine and water which is catalyzed by 1-methyladenosine nucleosidase (EC:3.2.2.13). 1-Methyladenine is a product of alkylation damage in DNA which can be repaired by damage reversal by oxidative demethylation, a reaction requiring ferrous iron and 2-oxoglutarate as cofactor and co-substrate, respectively (PMID:15576352). 1-Methyladenine is found to be associated with adenosine deaminase (ADA) deficiency, which is an inborn error of metabolism. 1-Methyladenine is the product of reaction between 1-methyladenosine and water which is catalyzed by 1-methyladenosine nucleosidase. (EC:3.2.2.13) KEIO_ID M074
3-Methyladenine
3-Methyladenine, also known as 3-ma nucleobase, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 3-Methyladenine exists in all living species, ranging from bacteria to humans. 3-Methyladenine has been detected, but not quantified, in several different foods, such as soft-necked garlics, chinese bayberries, burbots, amaranths, and tea. This could make 3-methyladenine a potential biomarker for the consumption of these foods. 3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC3.2.2.21). 3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC 3.2.2.21) [HMDB]. 3-Methyladenine is found in many foods, some of which are sacred lotus, evergreen huckleberry, swamp cabbage, and red rice. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID M030
7-Methyladenine
7-Methyladenine is part of the base excision repair pathway. In this pathway, alkylated DNA is hydrolysed via the enzyme DNA-3-methyladenine glycosylase II (EC 3.2.2.21), releasing 3-methyladenine, 3-methylguanine, 7-methylguanine and 7-methyladenine. This enzyme is responsible for the hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions. Base excision repair (BER) is a cellular mechanism that repairs damaged DNA throughout the cell cycle. Repairing DNA sequence errors is necessary so that mutations are not propagated or to remove lesions that may lead to breaks in the DNA during replication. Single bases in DNA can be chemically mutated, for example by deamination or alkylation, resulting in incorrect base-pairing, and consequently, mutations in the DNA. Base excision repair involves flipping the mutated base out of the DNA helix and repairing the base alone. There are two main enzymes used, DNA glycosylases and AP endonucleases. The DNA glycosylase is used to break the beta-N glycosidic bond to create an AP site. AP endonuclease recognizes this site and nicks the damaged DNA on the 5 side (upstream) of the AP site creating a free 3-OH. DNA polymerase, Pol I (human pol beta), extends the DNA from the free 3-OH using its exonuclease activity to replace the nucleotide of the damaged base, as well as a few downstream, followed by sealing of the new DNA strand by DNA ligase. In mammalian cells, this is done by LigIII in complex with the scaffold protein XRCC1. Usually, BER is divided into short-patch repair (where a single nucleotide is replaced) or long-patch repair (where 2-10 nucleotides are replaced). Mammalian long-patch repair includes PCNA and pol delta/epsilon for nucleotide resynthesis, FEN1 to cut of the flap including the damaged base, and LigI. 7-Methyladenine is part of the base excision repair pathway. In this pathway, alkylated DNA is hydrolysed via the enzyme DNA-3-methyladenine glycosylase II (EC 3.2.2.21), releasing 3-methyladenine, 3-methylguanine, 7-methylguanine and 7-methyladenine. This enzyme is responsible for the hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions. (Pathway Commons)
Tenofovir
C9H14N5O4P (287.07833740000007)
Tenofovir is only found in individuals that have used or taken this drug. Tenofovir, marketed by Gilead Sciences under the trade name Viread®, belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. [Wikipedia]Tenofovir inhibits the activity of HIV reverse transcriptase by competing with the natural substrate deoxyadenosine 5’-triphosphate and, after incorporation into DNA, by DNA chain termination. Specifically, the drugs are analogues of the naturally occurring deoxynucleotides needed to synthesize the viral DNA and they compete with the natural deoxynucleotides for incorporation into the growing viral DNA chain. However, unlike the natural deoxynucleotides substrates, NRTIs and NtRTIs (nucleoside/tide reverse transcriptase inhibitors) lack a 3-hydroxyl group on the deoxyribose moiety. As a result, following incorporation of an NRTI or an NtRTI, the next incoming deoxynucleotide cannot form the next 5-3 phosphodiester bond needed to extend the DNA chain. Thus, when an NRTI or NtRTI is incorporated, viral DNA synthesis is halted, a process known as chain termination. All NRTIs and NtRTIs are classified as competitive substrate inhibitors. C471 - Enzyme Inhibitor > C1589 - Reverse Transcriptase Inhibitor > C97452 - Nucleoside Reverse Transcriptase Inhibitor D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors C254 - Anti-Infective Agent > C281 - Antiviral Agent Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Tenofovir (GS 1278) is a nucleotide reverse transcriptase inhibitor to treat HIV and chronic Hepatitis B (HBV)[1].
D-erythro-Eritadenine
C9H11N5O4 (253.08110059999998)
D-erythro-Eritadenine is found in mushrooms. D-erythro-Eritadenine is isolated from the edible shitake mushroo D004791 - Enzyme Inhibitors
Deoxyeritadenine
Deoxyeritadenine is found in mushrooms. Deoxyeritadenine is a constituent of the edible shitake mushroom
6-Amino-9H-purine-9-propanoic acid
6-Amino-9H-purine-9-propanoic acid is found in mushrooms. 6-Amino-9H-purine-9-propanoic acid is isolated from Lentinus edodes (shiitake
LacCer(d18:1/20:0)
LacCer(d18:1/20:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called cytolipin H. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted. from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). Lactosylceramide (d18:1/20:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called cytolipin H. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted
Adefovir Dipivoxil
Adefovir Dipivoxil is only found in individuals that have used or taken this drug.Adefovir dipivoxil, previously called bis-POM PMEA, with trade names Preveon and Hepsera, is an orally-administered nucleotide analog reverse transcriptase inhibitor (ntRTI) used for treatment of hepatitis B. It is a failed treatment for HIV. [Wikipedia]Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA. The inhibition constant (Ki) for adefovir diphosphate for HBV DNA polymerase was 0.1 μM. Adefovir diphosphate is a weak inhibitor of human DNA polymerases alpha and gamma with Ki values of 1.18 μM and 0.97μM, respectively. J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors C471 - Enzyme Inhibitor > C1589 - Reverse Transcriptase Inhibitor > C97452 - Nucleoside Reverse Transcriptase Inhibitor D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors C254 - Anti-Infective Agent > C281 - Antiviral Agent Adefovir dipivoxil, an adenosine analogue, is an oral proagent of the nucleoside reverse transcriptase inhibitor Adefovir. Adefovir dipivoxil inhibits both the wild type and HBV Lamivudine-resistant strains[1][2]. Adefovir dipivoxil shows anti-orthopoxvirus activity.
(2R,3S)-3-(6-Amino-9H-purin-9-yl)nonan-2-ol
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D004791 - Enzyme Inhibitors
[(1R,5R)-5-(6-Aminopurin-9-yl)cyclohex-3-en-1-yl]methanol
2-[(6-Aminopurin-9-yl)methoxy]ethyl dihydrogen phosphate
2-Fluoroadenine
2-Fluoroadenine is a toxic purine bases. 2-Fluoroadenine has toxicity in nonproliferating and proliferating tumor cells. 2-Fluoroadenine can be used for researching anticancer[1].
2,6-Diaminopurine
2,6-diaminopurine, also known as 2-aminoadenine, is a member of the class of compounds known as 6-aminopurines. 6-aminopurines are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 2,6-diaminopurine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2,6-diaminopurine can be synthesized from adenine. 2,6-diaminopurine can also be synthesized into reversine. 2,6-diaminopurine can be found in broad bean, which makes 2,6-diaminopurine a potential biomarker for the consumption of this food product. 2,6-diaminopurine is a compound used to treat leukemia.[1] In August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting 2,6-diaminopurine and related organic molecules, including the DNA and RNA components adenine and guanine, may have been formed extraterrestrially in outer space . D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
2,6-Diamino-9-(2-hydroxyethoxymethyl)purine
C8H12N6O2 (224.10216920000002)
9-(2-Phosphonomethoxypropyl)adenine
C9H14N5O4P (287.07833740000007)
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
9-[2-(Phosphanylmethoxy)ethyl]purin-6-amine
C8H12N5OP (225.07794319999996)
Adenine monophosphate
Adenosine dialdehyde
Adenosine dialdehyde, a purine nucleoside analogue, is a potent inhibitor of S-Adenosylhomocysteine hydrolase (SAHH) (Ki=3.3 nM)[1]. Adenosine Dialdehyde exhibits potent anti-tumor activity in vivo and can be used for the cancer research[1][2].
arabinosyl-2-fluoroadenine
C10H12FN5O4 (285.08732840000005)
Tenofovir exalidex
C28H52N5O5P (569.3705871999999)
9H-Purine-9-butanoic acid, 6-amino-alpha-hydroxy-, methyl ester
C10H13N5O3 (251.10183480000003)
Hpmpa
C9H14N5O5P (303.07325240000006)
2-((6-Amino-9H-purin-9-yl)methyl)-5-methyl-3-o-tolylquinazolin-4(3H)-one
C22H19N7O (397.16510040000003)
Islatravir
C12H12FN5O3 (293.09241340000005)
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
2-(2-Hydroxyethylamino)-6-(3-chloroanilino)-9-isopropylpurine
C16H19ClN6O (346.13087939999997)
2',3'-Dialdehyde ATP
C10H14N5O13P3 (504.98009840000003)
9-(2-Phosphonylmethoxyethyl)-2,6-diaminopurine
C8H13N6O4P (288.07358680000004)
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents
Pradefovir
C17H19ClN5O4P (423.08631340000005)
4-Amino-1-(6-aminopurin-9-yl)pyrimidin-2-one
9-(1,3-Dioxolan-2-yl)purine-2,6-diamine
C8H10N6O2 (222.08652000000004)
1-(6-Aminopurin-9-yl)-5-methylpyrimidine-2,4-dione
(2S,3S,5R)-5-(6-Aminopurin-9-yl)-2-(2H-oxet-2-yl)oxolan-3-ol
(6-Aminopurin-9-yl) [hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate
C5H8N5O10P3 (390.94840580000005)