Compounds > adenosine-5'-carboxaldehyde
Page last updated: 2024-09-27

adenosine-5'-carboxaldehyde

Description

adenosine-5'-carboxaldehyde: potent inhibitor of S-adenosyl-L-homocysteine hydrolase; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5'-dehydroadenosine : A member of the class of adenosines that is 5'-dehydro derivative of adenosine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID443234
CHEMBL ID308037
CHEBI ID1958
SCHEMBL ID4776904
MeSH IDM0215151

Synonyms (18)

Synonym
CHEMBL308037 ,
bdbm50051435
5''-deoxy-5''-oxoadenosine
5''-dehydroadenosine
5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carbaldehyde
(2s,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-carbaldehyde
9-beta-d-ribo-pentodialdo-1,4-furanosyl-9h-purin-6-amine
3110-98-3
CHEBI:1958 ,
5'-deoxy-5'-oxoadenosine
5'-dehydroadenosine
adenosine, 5'-deoxy-5'-oxo-
adenosine-5'-carboxaldehyde
SCHEMBL4776904
Q27105535
DTXSID20953201
9-(pentodialdo-1,4-furanosyl)-9h-purin-6-amine
(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-carbaldehyde

Drug Classes (1)

ClassDescription
adenosinesAny purine ribonucleoside that is a derivative of adenosine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AdenosylhomocysteinaseRattus norvegicus (Norway rat)Ki0.04300.00840.02570.0430AID200096
AdenosylhomocysteinaseHomo sapiens (human)Ki0.04030.00000.18991.9300AID199279; AID199468; AID199471
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
one-carbon metabolic processAdenosylhomocysteinaseHomo sapiens (human)
S-adenosylmethionine cycleAdenosylhomocysteinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
adenosylselenohomocysteinase activityAdenosylhomocysteinaseRattus norvegicus (Norway rat)
adenosylhomocysteinase activityAdenosylhomocysteinaseHomo sapiens (human)
protein bindingAdenosylhomocysteinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
cytosolAdenosylhomocysteinaseRattus norvegicus (Norway rat)
nucleusAdenosylhomocysteinaseHomo sapiens (human)
endoplasmic reticulumAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
melanosomeAdenosylhomocysteinaseHomo sapiens (human)
extracellular exosomeAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID8423750% effective concentration required to reduce herpes simplex virus-1 (HSV- (TK) VMW 1837 strain)-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID125185Cytostatic activity against human lymphocyte Molt 4/clone 8 cell line1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199140Inhibition of human placental S-Adenosyl-homocysteine hydrolase at 1.0 (uM) concentration1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID200096Inhibitory activity against recombinant rat liver S-adenosyl-homocysteine hydrolase1993Journal of medicinal chemistry, Apr-02, Volume: 36, Issue:7
Adenosine-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
AID200099Rate constant for recombinant rat liver S-adenosyl-homocysteine hydrolase inactivation1993Journal of medicinal chemistry, Apr-02, Volume: 36, Issue:7
Adenosine-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
AID8479250% effective concentration required to reduce herpes simplex virus-2 (HSV-2 G strain)-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID218513Effective concentration required to reduce vesicular stomatitis virus (VSV)-induced cytopathicity in vero cells1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID218509Effective concentration required to reduce coxsackie virus B4-induced cytopathicity in vero cells1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID232028Second order rate constant for AdoHcy Hydrolase inactivation estimated as the ratio of k2/Ki1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Aristeromycin-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
AID199467Inhibition of S-adenosyl-L-homocysteine hydrolase, dissociation constant.1996Journal of medicinal chemistry, Oct-11, Volume: 39, Issue:21
Inactivation of S-adenosyl-L-homocysteine hydrolase by amide and ester derivatives of adenosine-5'-carboxylic acid.
AID199589Apparent inactivation rate constant (k2) for S-adenosyl-L-homocysteine hydrolase1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Aristeromycin-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
AID218510Effective concentration required to reduce parainfluenza-3-induced cytopathicity in vero cells1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199279concentration dependent inhibition of S-Adenosyl-homocysteine hydrolase was determined by Kitz and Wilson method1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID200098Ratio value is k2/Ki (1/nM 1/min)1993Journal of medicinal chemistry, Apr-02, Volume: 36, Issue:7
Adenosine-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
AID8423650% effective concentration required to reduce herpes simplex virus-1 (HSV- (TK) B2006 strain)-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID98560Cytostatic activity against murine leukemia L1210 cell line1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID9076150% effective concentration required to reduce cytomegalovirus (CMV Davis strain)-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199471Binding affinity towards purified recombinant human placental S-adenosyl-L-homocysteine hydrolase1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Aristeromycin-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
AID46557Cytostatic activity against human lymphocyte CEM cell line1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID21797550% effective concentration required to reduce vaccinia virus-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199142Inhibition of human placental S-Adenosyl-homocysteine hydrolase at 10.0 (uM) concentration; No activity detected1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199468Inhibition of S-adenosyl-L-homocysteine hydrolase, inactivation rate constant.1996Journal of medicinal chemistry, Oct-11, Volume: 39, Issue:21
Inactivation of S-adenosyl-L-homocysteine hydrolase by amide and ester derivatives of adenosine-5'-carboxylic acid.
AID199139Inhibition of human placental S-Adenosyl-homocysteine hydrolase at 0.1 (uM) concentration1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199138Inhibition of human placental S-Adenosyl-homocysteine hydrolase at 0.01 (uM) concentration1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID218512Effective concentration required to reduce sindbis virus-induced cytopathicity in vero cells1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199144Inhibition of human placental S-Adenosyl-homocysteine hydrolase at 100.0 (uM) concentration; No activity detected1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID231779Ratio of concentration and time dependent inhibition of AdoHcy Hydrolase.1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID280941Cytotoxicity against mouse L1210/0 cells after 48 hrs2007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
Probing the anticancer activity of nucleoside analogues: a QSAR model approach using an internally consistent training set.
AID229491Inhibition of S-adenosyl-L-homocysteine hydrolase, second order rate constant k2/KI1996Journal of medicinal chemistry, Oct-11, Volume: 39, Issue:21
Inactivation of S-adenosyl-L-homocysteine hydrolase by amide and ester derivatives of adenosine-5'-carboxylic acid.
AID9076050% effective concentration required to reduce cytomegalovirus (CMV AD-169 strain)-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID63602Minimum inhibitory concentration required to effect a microscopically visible change of cell morphology in human embryonic skin-muscle (E6SM) cell culture.1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID218511Effective concentration required to reduce reovirus-1-induced cytopathicity in vero cells1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID8588350% effective concentration required to reduce herpes simplex virus-1 (HSV-1 KOS strain)-induced cytopathicity1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID71883Cytostatic activity against murine mammary carcinoma FM3A cell line1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID199145Time dependent inhibition of S-Adenosyl-homocysteine hydrolase was determined by Kitz and Wilson method1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
AID8253250% Cytostatic concentration required to inhibit human erythroleukemic (HEL) cell proliferation1997Journal of medicinal chemistry, May-23, Volume: 40, Issue:11
Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (80.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
adenosine-5'-carboxylic acid[no description available]medium10purine nucleoside
5'-n-methylcarboxamideadenosine[no description available]medium10
9-(2,3-dihydroxypropyl)adenine, (s)-isomer[no description available]medium10
1-deazaadenosine[no description available]medium10
brivudine[no description available]medium20
fluorouracil[no description available]medium10nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
floxuridine[no description available]medium10nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
idoxuridine[no description available]medium10organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
bromodeoxyuridine[no description available]medium10pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
cytarabine[no description available]medium10beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
trifluridine[no description available]medium10nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
adefovir[no description available]medium106-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine[no description available]medium10
thymine arabinoside[no description available]medium10N-glycosyl compound
edoxudin[no description available]medium10pyrimidine 2'-deoxyribonucleoside
n-(2-(hydroxyethoxy)methyl)-5-methyluracil[no description available]medium10
5-fluoro-1-((2-hydroxyethoxy)methyl)uracil[no description available]medium10
5-hydroxymethyl-2'-deoxyuridine[no description available]medium10pyrimidine 2'-deoxyribonucleoside
msh release-inhibiting hormone[no description available]medium10oligopeptide
5-hydroxy-2'-deoxyuridine[no description available]medium10
5-formyl-2'-deoxyuridine[no description available]medium10
5-nitro-2'-deoxyuridine[no description available]medium10
5-vinyl-2'-deoxyuridine[no description available]medium10
5-propyl-2'-deoxyuridine[no description available]medium10
5-ethynyl-2'-deoxyuridine[no description available]medium10
5-cyano-2'-deoxyuridine[no description available]medium10
5-(2-iodovinyl)-2'-deoxyuridine[no description available]medium10
acyclovir[no description available]medium102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
9-((2-phosphonylmethoxy)ethyl)guanine[no description available]medium10phosphoethanolamine
adenosine[no description available]medium10adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
puromycin aminonucleoside[no description available]low003'-deoxyribonucleoside;
adenosines
cordycepin[no description available]low003'-deoxyribonucleoside;
adenosines		antimetabolite;
nucleoside antibiotic
2-fluoroadenosine[no description available]low00adenosines;
organofluorine compound
dideoxyadenosine[no description available]low00adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
sinefungin[no description available]low00adenosines;
non-proteinogenic alpha-amino acid		antifungal agent;
antimicrobial agent
nucleocidin[no description available]low006-aminopurines;
adenosines;
diol;
organofluorine compound;
sulfamate ester		antibacterial agent;
bacterial metabolite;
nucleoside antibiotic;
protein synthesis inhibitor;
trypanocidal drug
2'-o-methyladenosine[no description available]low00adenosines;
ether		fungal metabolite
clofarabine[no description available]low00adenosines;
organofluorine compound		antimetabolite;
antineoplastic agent
n(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine[no description available]low00adenosines;
monocarboxylic acid amide;
organoiodine compound		adenosine A3 receptor agonist
s-adenosylhomocysteine[no description available]low00adenosines;
amino acid zwitterion;
homocysteine derivative;
homocysteines;
organic sulfide		cofactor;
EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor;
EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor;
epitope;
fundamental metabolite
5'-deoxyadenosine[no description available]low005'-deoxyribonucleoside;
adenosines		Escherichia coli metabolite;
human metabolite;
mouse metabolite
s-adenosyl-3-methylthiopropylamine[no description available]low00adenosines;
sulfonium compound		Escherichia coli metabolite;
human urinary metabolite;
mouse metabolite;
rat metabolite
2'-deoxy-2-fluoroadenosine[no description available]low00adenosines;
organofluorine compound
adenosine-5'-(n-ethylcarboxamide)[no description available]low00adenosines;
monocarboxylic acid amide		adenosine A1 receptor agonist;
adenosine A2A receptor agonist;
antineoplastic agent;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
vasodilator agent
adenosine-5'-(N-propyl)carboxamide[no description available]low00adenosines;
monocarboxylic acid amide
2-(4-(2-carboxyethyl)phenethylamino)-5'-n-ethylcarboxamidoadenosine[no description available]low00adenosines;
dicarboxylic acid monoamide;
monocarboxylic acid		adenosine A2A receptor agonist;
anti-inflammatory agent
5'-chloro-5'-deoxyadenosine[no description available]low00adenosines
3-iodo-4-aminobenzyl-5'-N-methylcarboxamidoadenosine[no description available]low00adenosines;
monocarboxylic acid amide;
organoiodine compound
succinyladenosine[no description available]low00adenosines;
amino dicarboxylic acid;
L-aspartic acid derivative		metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Cytomegalovirus0low10
Experimental Mammary Neoplasms0low10
Leukemia L 12100low10
Leukemia L12100low10
Mammary Neoplasms, Experimental0low10
Neoplasms, Experimental Mammary0low10