Compounds > 9-(2',3'-dihydroxycyclopentan-1'-yl)adenine
Page last updated: 2024-12-06

9-(2',3'-dihydroxycyclopentan-1'-yl)adenine

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Description

9-(2',3'-dihydroxycyclopentan-1'-yl)adenine: inhibitor of S-adenosylhomocysteine hydrolase; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73651
CHEMBL ID301499
SCHEMBL ID2421602
MeSH IDM0218125

Synonyms (20)

Synonym
9-(2',3'-dihydroxycyclopentan-1'-yl)adenine
dhcaa
(1r,2s,3r)-3-(6-aminopurin-9-yl)cyclopentane-1,2-diol
(-)-1,2-cyclopentanediol, 3-(6-amino-9h-purin-9-yl)-, (1r,2s,3r)-
125409-63-4
CHEMBL301499 ,
(1r,2s,3r)-3-(6-amino-9h-purin-9-yl)cyclopentane-1,2-diol
3-(6-amino-purin-9-yl)-cyclopentane-1,2-diol
bdbm50006218
(+/-)-(1r*,2s*,3r*)-3-(6-amino-9h-purin-9-yl)-1,2-cyclopentanediol
CZASVOKHBMDKGF-JKMUOGBPSA-N
SCHEMBL2421602
DTXSID00925128
mfcd00912164
1,2-cyclopentanediol, 3-(6-amino-9h-purin-9-yl)-, (1r,2s,3r)-rel-
129706-34-9
1,2-cyclopentanediol, 3-(6-amino-9h-purin-9-yl)-, (1r,2s,3r)-
EN300-1588055
PD121383
Z2651693367
[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)6.01880.00152.11118.7000AID1152849; AID1152850; AID328971
AdenosylhomocysteinaseHomo sapiens (human)Ki0.01200.00000.18991.9300AID199453
[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 (14)

Assay IDTitleYearJournalArticle
AID328971Inhibition of human recombinant SAHH at 1000 uM2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase.
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.
AID235642Selectivity index was evaluated [Selectivity = (CC50 / EC50) against Hepatitis B virus in human hepatoblastoma cell line]1998Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12
Does the anti-hepatitis B virus activity of (+)-5'-noraristeromycin exist in its 4'-epimer and 4'-deoxygenated derivatives?
AID1152851Genotoxicity in Salmonella typhi in presence of liver S9 fraction2014Bioorganic & medicinal chemistry letters, Jun-15, Volume: 24, Issue:12
Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.
AID328969Inhibition of Plasmodium falciparum recombinant SAHH at 1000 uM2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase.
AID86873Effective concentration against Hepatitis B virus in human hepatoblastoma cell line1998Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12
Does the anti-hepatitis B virus activity of (+)-5'-noraristeromycin exist in its 4'-epimer and 4'-deoxygenated derivatives?
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.
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.
AID1152852Genotoxicity in Salmonella typhi in absence of liver S9 fraction2014Bioorganic & medicinal chemistry letters, Jun-15, Volume: 24, Issue:12
Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.
AID328972Selectivity ratio of human recombinant SAHH to Plasmodium falciparum recombinant SAHH2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase.
AID86871Cytotoxic concentration against Hepatitis B virus in human hepatoblastoma cell line1998Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12
Does the anti-hepatitis B virus activity of (+)-5'-noraristeromycin exist in its 4'-epimer and 4'-deoxygenated derivatives?
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.
AID86872Effective concentration against Hepatitis B virus in human hepatoblastoma cell line1998Journal of medicinal chemistry, Jun-04, Volume: 41, Issue:12
Does the anti-hepatitis B virus activity of (+)-5'-noraristeromycin exist in its 4'-epimer and 4'-deoxygenated derivatives?
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (42.86)18.2507
2000's3 (42.86)29.6817
2010's1 (14.29)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: 12.24

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 Index12.24 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.24)

All Compounds (24.57)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
9-(2',3'-dihydroxycyclopent-4'-enyl)adenine
9-(2',3'-dihydroxycyclopent-4'-enyl)adenine: structure given in first source; S-adenosyl homocysteine hydrolase antagonist		2.420
thymidine
[no description available]		210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
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
lamivudine
[no description available]		1.9910monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.6930adenosines;
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		2.6930
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		2.4220
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
5'-noraristeromycin
5'-noraristeromycin: structure given in first source		2.4220
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.		1.9810adenosines;
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
9-(2',3'-dihydroxycyclopent-4'-enyl)adenine
[no description available]		2.4220
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.		1.9810organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
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
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		0210