Classification Term: 2817

Purine 2'-deoxyribonucleoside monophosphates (ontology term: CHEMONTID:0002141)

Purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2." []

found 8 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Purine deoxyribonucleoside monophosphates

Child Taxonomies: There is no child term of current ontology term.

2'-Deoxyguanosine 5'-monophosphate

{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

C10H14N5O7P (347.06308240000004)


2-Deoxyguanosine 5-monophosphate, also known as deoxyguanylic acid or 2-deoxy-GMP, belongs to the class of organic compounds known as purine 2-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. 2-Deoxyguanosine 5-monophosphate is a purine 2-deoxyribonucleoside 5-monophosphate having guanine as the nucleobase. It exists in all living species, ranging from bacteria to humans. Within humans, 2-deoxyguanosine 5-monophosphate participates in a number of enzymatic reactions. In particular, 2-deoxyguanosine 5-monophosphate can be converted into dGDP which is mediated by the enzyme guanylate kinase. In addition, 2-deoxyguanosine 5-monophosphate can be converted into deoxyguanosine through its interaction with the enzyme cytosolic purine 5-nucleotidase. In humans, 2-deoxyguanosine 5-monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. 2-Deoxyguanosine 5-monophosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis . [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

2'-Deoxyadenosine 5'-phosphate

{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

C10H14N5O6P (331.06816740000005)


Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleic acid AMP, or adenosine monophosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Additionally, the monophosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis. It is a monomer used in DNA. Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a -N9-glycosidic bond. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1]. 2′-Deoxyadenosine 5′-monophosphate, a nucleic acid AMP derivative, is a deoxyribonucleotide found in DNA. 2′-Deoxyadenosine 5′-monophosphate can be used to study adenosine-based interactions during DNA synthesis and DNA damage[1].

   

dIMP

[(2R,3S,4R,5R)-3-Hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

C10H13N4O7P (332.0521838)


dIMP is a deoxyribonucleoside and is considered a derivative of the nucleoside inosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2 position of its ribose sugar moiety. The hydrolytic deamination of dAMP residues in DNA yields dIMP residues. The deamination of adenine residues in DNA generates hypoxanthine, which is mutagenic since it can pair not only with thymine but also with cytosine and therefore would result in A-T to G-C transitions after DNA replication. Hypoxanthine DNA glycosylase (EC 3.2.2.15) excises hypoxanthine from DNA containing dIMP residues in mammalian cells. (PMID: 10684927, 8016081) [HMDB] dIMP is a deoxyribonucleoside and is considered a derivative of the nucleoside inosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2 position of its ribose sugar moiety. The hydrolytic deamination of dAMP residues in DNA yields dIMP residues. The deamination of adenine residues in DNA generates hypoxanthine, which is mutagenic since it can pair not only with thymine but also with cytosine and therefore would result in A-T to G-C transitions after DNA replication. Hypoxanthine DNA glycosylase (EC 3.2.2.15) excises hypoxanthine from DNA containing dIMP residues in mammalian cells. (PMID: 10684927, 8016081). Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

8-Oxo-dGMP

{[(3S)-5-(2-amino-6,8-dioxo-6,7,8,9-tetrahydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

C10H14N5O8P (363.05799740000003)


8-Oxo-dGMP is a metabolite of 8-oxo-dGTP. 8-Oxo-7,8-dihydro-2-deoxyguanosine 5-triphosphate (8-oxo-dGTP) is a potent mutagenic substrate for DNA synthesis. 8-Oxo-dGTP is rapidly degraded to 8-oxo-dGMP by cellular 8-oxo-dGTPase activity. 8-Oxo-dGMP is further degraded to 8-oxo-deoxyguanosine by a nucleotidase. 8-Oxo-dGMP is the most preferred substrate of this nucleotidase enzyme (PMID: 7819228). The human MutT homologue (hMTH1), an 8-oxo-dGTPase, prevents misincorporation of 8-oxo-dGTP into DNA by hydrolyzing it to 8-oxo-dGMP. hMTH1 mRNA is overexpressed in human renal cell carcinomas and breast tumors. Likewise, elevated levels of hMTH1 protein have also been detected in brain tumors. (PMID: 12757855) [HMDB] 8-Oxo-dGMP is a metabolite of 8-oxo-dGTP. 8-Oxo-7,8-dihydro-2-deoxyguanosine 5-triphosphate (8-oxo-dGTP) is a potent mutagenic substrate for DNA synthesis. 8-Oxo-dGTP is rapidly degraded to 8-oxo-dGMP by cellular 8-oxo-dGTPase activity. 8-Oxo-dGMP is further degraded to 8-oxo-deoxyguanosine by a nucleotidase. 8-Oxo-dGMP is the most preferred substrate of this nucleotidase enzyme (PMID: 7819228). The human MutT homologue (hMTH1), an 8-oxo-dGTPase, prevents misincorporation of 8-oxo-dGTP into DNA by hydrolyzing it to 8-oxo-dGMP. hMTH1 mRNA is overexpressed in human renal cell carcinomas and breast tumors. Likewise, elevated levels of hMTH1 protein have also been detected in brain tumors. (PMID: 12757855).

   

2-hydroxy-dAMP

{[(2R,3S,5R)-5-(6-amino-2-hydroxy-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

C10H14N5O7P (347.06308240000004)


2-hydroxy-damp is a substrate for: 7,8-dihydro-8-oxoguanine triphosphatase.

   

clofarabind-5'-monophosphate

{[(2S,3S,4S,5S)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

C10H12ClFN5O6P (383.0197744)


clofarabind-5-monophosphate is a metabolite of clofarabine. Clofarabine is a purine nucleoside antimetabolite marketed in the U.S. and Canada as Clolar. In Europe and Australia/New Zealand the product is marketed under the name Evoltra. It is FDA-approved for treating relapsed or refractory acute lymphoblastic leukaemia (ALL) in children after at least two other types of treatment have failed. It is not known if it extends life expectancy. (Wikipedia)

   

Guadecitabine

{[5-(4-amino-2-oxo-1,2-dihydro-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy}({[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy})phosphinic acid

C18H24N9O10P (557.1383694)


   

thioinosine monophosphate

{[3-hydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)-4-sulfanyloxolan-2-yl]methoxy}phosphonic acid

C10H13N4O7PS (364.02425580000005)