Compounds > 9-(2',3'-dihydroxycyclopent-4'-enyl)adenine
Page last updated: 2024-12-04

9-(2',3'-dihydroxycyclopent-4'-enyl)adenine

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Description

9-(2',3'-dihydroxycyclopent-4'-enyl)adenine: structure given in first source; S-adenosyl homocysteine hydrolase antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID490351
CHEMBL ID299961
SCHEMBL ID2418669
MeSH IDM0154454
PubMed CID1468
SCHEMBL ID630675
MeSH IDM0154454

Synonyms (26)

Synonym
avs-3586
dhcea
ohca
(1s,2r,5r)-5-(6-aminopurin-9-yl)cyclopent-3-ene-1,2-diol
(-)-9-[trans-2'-trans-3'-dihydroxycyclopent-4'-enyl]-adenine
CHEMBL299961 ,
(1''r,2''s,3''r)-9-(2'',3''-dihydroxycyclopent-4''-enyl)adenine
(1s,2r,5r)-5-(6-amino-purin-9-yl)-cyclopent-3-ene-1,2-diol
bdbm50006215
5-(6-amino-purin-9-yl)-cyclopent-3-ene-1,2-diol
(1s,2r,5r)-5-(6-amino-9h-purin-9-yl)cyclopent-3-ene-1,2-diol
RQPALADHFYHEHK-JKMUOGBPSA-N
SCHEMBL2418669
5-(6-amino-9h-purin-9-yl)cyclopent-3-ene-1,2-diol
112318-09-9
5-(6-aminopurin-9-yl)cyclopent-3-ene-1,2-diol
ttdhc
9-(2',3'-dihydroxycyclopent-4'-enyl)adenine
3-cyclopentene-1,2-diol, 5-(6-amino-9h-purinyl-9-yl)-, (1alpha,2alpha,5beta)-
9-(2',trans-3'-dihydroxycyclopent-4'-enyl)adenine
5'-norneplanocin a
5'-dhca
SCHEMBL630675
DTXSID20920731
3-cyclopentene-1,2-diol,5-(6-amino-9h-purin-9-yl)-,(1r,2s,5s)-rel
PD041906
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AdenosylhomocysteinaseHomo sapiens (human)IC50 (µMol)4.88300.00152.11118.7000AID1152849; AID1152850; AID199465; AID576802
AdenosylhomocysteinaseHomo sapiens (human)Ki0.04500.00000.18991.9300AID199453; AID199928
[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 (2)

Processvia Protein(s)Taxonomy
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
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 (23)

Assay IDTitleYearJournalArticle
AID199446Percentage enzyme activity remaining was measured by the inhibition S-adenosyl-L-homocysteine hydrolase from bovine liver at 100 uM1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.
AID301695Inactivation of human recombinant S-adenosyl-L-homocysteine hydrolase NADH form expressed in Escherichia coli JM109 assessed by measuring fluorescence2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi.
AID108462Inhibitory concentration required to reduce virus Plaque formation (measles)1996Journal of medicinal chemistry, Sep-13, Volume: 39, Issue:19
New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A.
AID199457Kinetic constant against bovine liver S-adenosyl-L-homocysteine hydrolase (AdoHcy).1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
4'-modified analogues of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolase.
AID199465In vitro inhibitory activity against recombinant S-adenosyl-L-homocysteine hydrolase obtained from human placenta2004Bioorganic & medicinal chemistry letters, May-03, Volume: 14, Issue:9
Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase.
AID1152849Inhibition of recombinant human AHCY using SAH as substrate assessed as formation of homocysteine after 10 mins2014Bioorganic & medicinal chemistry letters, Jun-15, Volume: 24, Issue:12
Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.
AID54287NAD+ content of the enzyme tetramer was measured by HPLC on a C 18 reverse-phase column1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl) derivatives of adenine and 3-deazaadenine: potent inhibitors of bovine liver S-adenosylhomocysteine hydrolase.
AID1152850Inhibition of AHCY in human SH-SY5Y cells assessed as formation of homocysteine after 48 hrs by HPLC analysis2014Bioorganic & medicinal chemistry letters, Jun-15, Volume: 24, Issue:12
Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.
AID216966Cytotoxic concentration required to reduce the number of Vero cells by 50%1996Journal of medicinal chemistry, Sep-13, Volume: 39, Issue:19
New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A.
AID233173Ratio of kinetic constant to inhibitory activity against bovine liver S-adenosyl-L-homocysteine hydrolase(AdoHcy).1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
4'-modified analogues of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolase.
AID301704Inactivation of Trypanosoma cruzi recombinant S-adenosyl-L-homocysteine hydrolase NAD+ form expressed in Escherichia coli JM109 assessed as reduction of NAD+ to NADH2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi.
AID301696Inactivation of Trypanosoma cruzi recombinant S-adenosyl-L-homocysteine hydrolase NADH form expressed in Escherichia coli JM109 assessed by measuring fluorescence2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi.
AID576802Inhibition of human placental AdoHcy hydrolase expressed in Escherichia coli JM1092011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
X-ray crystal structure and binding mode analysis of human S-adenosylhomocysteine hydrolase complexed with novel mechanism-based inhibitors, haloneplanocin A analogues.
AID199444Percentage enzyme activity remaining was measured by the inhibition S-adenosyl-L-homocysteine hydrolase from bovine liver at 1 uM1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.
AID199927Tested for S-adenosyl-homocysteine hydrolase activity using coupled assay method, expressed as % residual enzyme activity1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl) derivatives of adenine and 3-deazaadenine: potent inhibitors of bovine liver S-adenosylhomocysteine hydrolase.
AID199928Time course of inactivation of bovine liver S-adenosyl-homocysteine hydrolase1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl) derivatives of adenine and 3-deazaadenine: potent inhibitors of bovine liver S-adenosylhomocysteine hydrolase.
AID199442Percentage enzyme activity remaining was measured by the inhibition S-adenosyl-L-homocysteine hydrolase from bovine liver at 0.01 uM1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.
AID216404Inhibitory concentration required to reduce virus -induced cytopathicity (VSV)1996Journal of medicinal chemistry, Sep-13, Volume: 39, Issue:19
New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A.
AID301703Inactivation of human recombinant S-adenosyl-L-homocysteine hydrolase NAD+ form expressed in Escherichia coli JM109 assessed as reduction of NAD+ to NADH2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi.
AID199453Inhibitory activity against bovine liver S-adenosyl-L-homocysteine hydrolase (AdoHcy).1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
4'-modified analogues of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolase.
AID199443Percentage enzyme activity remaining was measured by the inhibition S-adenosyl-L-homocysteine hydrolase from bovine liver at 0.1 uM1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.
AID199445Percentage enzyme activity remaining was measured by the inhibition S-adenosyl-L-homocysteine hydrolase from bovine liver at 10 uM1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.
AID141799Inhibitory concentration required to reduce virus Plaque formation (mumps)1996Journal of medicinal chemistry, Sep-13, Volume: 39, Issue:19
New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (27.78)18.7374
1990's7 (38.89)18.2507
2000's4 (22.22)29.6817
2010's2 (11.11)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.85

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.85 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ribavirin
Rebetron: Rebetron is tradename		2.03101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
aristeromycin
aristeromycin: RN given refers to (1R-(1alpha,2alpha,3beta,5alpha)-isomer		2.4220
neplanocin a
neplanocin A: neplanocins are antitumor antibiotics & carbocyclic analogs of purine nucleosides from Ampullarilla regularis A11079; see also neplanocin B, neplanocin C, neplanocin D & neplanocin F; structure in first source; a potent inhibitor of S-adenosylhomocysteine hydrolase		3.2660
9-(2',3'-dihydroxycyclopentan-1'-yl)adenine
9-(2',3'-dihydroxycyclopentan-1'-yl)adenine: inhibitor of S-adenosylhomocysteine hydrolase; structure given in first source		2.4220
5'-methylthioadenosine
5'-methylthioadenosine: structure. 5'-S-methyl-5'-thioadenosine : Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.		1.9710thioadenosinealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
adenine
[no description available]		2.02106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
thymidine
[no description available]		210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		1.9910aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
dinitrofluorobenzene
Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.		210C-nitro compound;
organofluorine compound		agrochemical;
allergen;
chromatographic reagent;
EC 2.7.3.2 (creatine kinase) inhibitor;
protein-sequencing agent;
spectrophotometric reagent
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		3.68100adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
aristeromycin
aristeromycin: RN given refers to (1R-(1alpha,2alpha,3beta,5alpha)-isomer		1.9810
3-deazaaristeromycin
3-deazaaristeromycin: antagonist of S-adenosylhomocysteinase		1.9810
neplanocin a
neplanocin A: neplanocins are antitumor antibiotics & carbocyclic analogs of purine nucleosides from Ampullarilla regularis A11079; see also neplanocin B, neplanocin C, neplanocin D & neplanocin F; structure in first source; a potent inhibitor of S-adenosylhomocysteine hydrolase		2.8940
3-deazaneplanocin
3-deazaneplanocin: S-adenosylhomocysteine hydrolase antagonist		1.9710
9-(2',3'-dihydroxycyclopentan-1'-yl)adenine
9-(2',3'-dihydroxycyclopentan-1'-yl)adenine: inhibitor of S-adenosylhomocysteine hydrolase; structure given in first source		2.420
homocysteine
Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.		2.8940amino acid zwitterion;
homocysteine;
serine family amino acid		fundamental metabolite;
mouse metabolite
glycidyl nitrate
glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.		210
eritadenine
eritadenine: isolated from Lentinula edodes (Shiitake mushroom); inhibits S-adenosyl-L-homocysteine hydrolase activity		2.0210
s-adenosylhomocysteine
S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.		2.8940adenosines;
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
adenosine kinase
Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.		1.9710
s-adenosylmethionine
(R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.		3.0750organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		02.3820
Experimental Leukemia
[description not available]		01.9710
Cytomegalovirus
A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.		01.9910
Adjuvant Arthritis
[description not available]		0210
Anasarca
[description not available]		0210
Delayed Hypersensitivity
[description not available]		0210
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		0210