Page last updated: 2024-11-08

cf 1743

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID493485
CHEMBL ID344738
SCHEMBL ID17709503
MeSH IDM0485626

Synonyms (20)

Synonym
3-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2-one
cf1743
6-(4-pentyl-phenyl)-3-((2r,4s,5r)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3h-furo[2,3-d]pyrimidin-2-one
CHEMBL344738
3-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2-one
unii-5xgi48q2dh
5xgi48q2dh ,
319425-66-6
cf-1743
furo(2,3-d)pyrimidin-2(3h)-one, 3-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-6-(4-pentylphenyl)-
3-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2(3h)-one
MFGSDSRTGUVZQG-DFQSSKMNSA-N ,
(2r,4s,5r)(4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2(3h)-one
DTXSID60185781
SCHEMBL17709503
bdbm50481116
Q5427311
furo[2,3-d]pyrimidin-2(3h)-one,3-(2-deoxy-b-d-erythro-pentofuranosyl)-6-(4-pentylphenyl)-
3-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2(3h)-one
AKOS040748112

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" We also demonstrated a markedly enhanced oral bioavailability of the prodrugs versus the parent drug in mice."( Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues.
Andrei, G; Balzarini, J; Camarasa, MJ; De Meester, I; Diez-Torrubia, A; Snoeck, R; Velázquez, S, 2011
)
0.37
[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)
Thymidine kinaseHuman herpesvirus 3 strain Oka vaccineIC50 (µMol)3.30003.30003.30003.3000AID445335
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinaseHuman herpesvirus 3 strain Oka vaccineKm1.58001.58001.58001.5800AID445336
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (61)

Assay IDTitleYearJournalArticle
AID588198Aqueous solubility of the compound at 25 DegC after 24 hrs2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues.
AID296677Antiviral activity against HCMV Davis in HEL cells assessed as reduction of virus plaque formation after 7 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID1782698Antiviral activity against Varicella zoster virus assessed as inhibition of viral replication2021European journal of medicinal chemistry, Aug-05, Volume: 220Phenoxazine nucleoside derivatives with a multiple activity against RNA and DNA viruses.
AID304885Antiviral activity against TK- VZV YS in HEL cells after 5 days2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID217806Evaluated for the anti-VZV, the concentration of compounds in uM required to reduce VZVTK-YS-R ( thymidine kinase-deficient strain ) plaque formation after 5 days in HEL cell cultures compared to untreated controls.2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID258991Antiviral activity against Varicella-Zoster virus YS/R strain2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
AID415401Cytotoxicity against human HEL cells2009Bioorganic & medicinal chemistry, Apr-15, Volume: 17, Issue:8
Alkenyl substituted bicyclic nucleoside analogues retain nanomolar potency against Varicella Zoster Virus.
AID246486Effective concentration required to reduce thymidine kinase-Varicella Zoster virus VZV 07/1 plaque formation by using DMSO as solvent2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID445335Displacement of [CH3-3H]deoxythymidine from Varicella zoster virus recombinant thymidine kinase after 30 mins2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
2'-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743.
AID216465Antiviral activity against Varicella-Zoster virus (OKA)2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Bicyclic anti-VZV nucleosides: thieno analogues bearing an alkylphenyl side chain have reduced antiviral activity.
AID1055505Antiviral activity against Herpes simplex virus 1 KOS infected in HEL cells assessed as inhibition of virus-induced cytopathicity2013European journal of medicinal chemistry, , Volume: 70Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.
AID258989Antiviral activity against Varicella-Zoster virus YS strain2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
AID246324Effective concentration required to reduce Varicella Zoster virus OKA plaque formation by using DMSO as solvent2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID296675Antiviral activity against thymidine kinase deficient VZV YS/R in HEL cells assessed as reduction of virus plaque formation after 5 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID296679Cytotoxicity against HEL cells after 3 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID296673Antiviral activity against TK+ VZV OKA in HEL cells assessed as reduction of virus plaque formation after 5 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID296678Cytotoxicity against HEL cells assessed as alteration in cell morphology after 3 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID296674Antiviral activity against thymidine kinase deficient VZV 07/1 in HEL cells assessed as reduction of virus plaque formation after 5 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID586282Cytotoxicity against HEL cells assessed as alteration of cell morphology2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues.
AID1055503Antiviral activity against acyclovir-resistant thymidine kinase-deficient Herpes simplex virus 1 KOS infected in HEL cells assessed as inhibition of virus-induced cytopathicity2013European journal of medicinal chemistry, , Volume: 70Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.
AID588201Antiviral activity against Varicella zoster virus OKA infected in HEL cells assessed as reduction in virus induced cytopathicity2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues.
AID445336Activity at Varicella zoster virus recombinant thymidine kinase assessed as 5-monophosphate BCNA formation after 60 mins by HPLC2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
2'-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743.
AID415399Antiviral activity against Varicella Zoster virus Oka infected in HEL cells assessed as reduction in viral plaque formation after 5 days2009Bioorganic & medicinal chemistry, Apr-15, Volume: 17, Issue:8
Alkenyl substituted bicyclic nucleoside analogues retain nanomolar potency against Varicella Zoster Virus.
AID245935Cytotoxic concentration required to inhibit Hel cell growth by using DMSO as solvent2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID445341Cytotoxicity against human HEL cells assessed as alteration of cell morphology by microscopy2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
2'-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743.
AID217659Evaluated for the anti-VZV activity, the concentration of compounds in uM required to reduce VZV OKA Plaque formation after 5 days in HEL cell cultures compared to untreated controls.2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID217512Minimal cytotoxic concentration, the concentration required to cause a microscopically visible alteration of normal cell morphology. 2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID304888Inhibition of VZV-TK catalyzed dThd phosphorylation2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID588202Cytotoxicity against HEL cells assessed as inhibition of cell proliferation2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues.
AID258993Antiviral activity against human cytomegalovirus Davis strain2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
AID217670Evaluated for the anti-VZV activity, the concentration of compounds in uM required to reduce VZV TS plaque formation after 5 days in HEL cell cultures compared to untreated controls.2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID87769Cytotoxic concentration required to inhibit Hel cell growth2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Bicyclic anti-VZV nucleosides: thieno analogues bearing an alkylphenyl side chain have reduced antiviral activity.
AID217511cytostatic concentration required to reduce the HEL cell number by 50%. after 5 days in the absence of virus2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID1055501Cytotoxicity against HEL cells2013European journal of medicinal chemistry, , Volume: 70Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.
AID258990Antiviral activity against Varicella-Zoster virus 07/1 strain2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
AID16473logarithm of the octanol-water partition coefficient for the compound2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID217665Evaluated for the anti-VZV, the concentration of compounds in uM required to reduce VZVTK-07 ( thymidine kinase-deficient strain ) plaque formation after 5 days in HEL cell cultures compared to untreated controls.2000Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
AID304886Cytotoxicity against HEL cells assessed as alteration in cell morphology2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID258992Antiviral activity against human cytomegalovirus AD169 strain2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
AID244767Minimal cytotoxic concentration required to alter microscopically detectable cell morphology2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID237354Calculated partition coefficient (clogP)2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID415400Antiviral activity against Varicella Zoster virus YS infected in HEL cells assessed as reduction in viral plaque formation after 5 days2009Bioorganic & medicinal chemistry, Apr-15, Volume: 17, Issue:8
Alkenyl substituted bicyclic nucleoside analogues retain nanomolar potency against Varicella Zoster Virus.
AID216467Antiviral activity against Varicella-Zoster virus (YS)2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Bicyclic anti-VZV nucleosides: thieno analogues bearing an alkylphenyl side chain have reduced antiviral activity.
AID1055502Antiviral activity against Feline herpesvirus infected in cat CRFK cells assessed as inhibition of virus-induced cytopathicity2013European journal of medicinal chemistry, , Volume: 70Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.
AID445338Antiviral activity against Varicella zoster virus OKA infected human HEL cells assessed as reduction in viral plaque formation after 5 days2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
2'-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743.
AID296676Antiviral activity against HCMV AD169 in HEL cells assessed as reduction of virus plaque formation after 7 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID296672Antiviral activity against TK+ VZV YS in HEL cells assessed as reduction of virus plaque formation after 5 days2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core.
AID258994Cytotoxic activity against cultured human embryonic lung (HEL) cells2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
AID87770Minimal cytotoxic concentration, required to alter microscopically detectable cell morphology2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Bicyclic anti-VZV nucleosides: thieno analogues bearing an alkylphenyl side chain have reduced antiviral activity.
AID246446Effective concentration required to reduce thymidine kinase-Varicella Zoster virus YS/R plaque formation by using DMSO as solvent2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID304882Antiviral activity against TK+ VZV OKA in HEL cells after 5 days2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID304887Cytotoxicity against HEL cells2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID304883Antiviral activity against TK+ VZV YS in HEL cells after 5 days2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID415402Inhibition of Varicella Zoster virus thymidine kinase-mediated [3H]thymidine phosphorylation2009Bioorganic & medicinal chemistry, Apr-15, Volume: 17, Issue:8
Alkenyl substituted bicyclic nucleoside analogues retain nanomolar potency against Varicella Zoster Virus.
AID1055504Antiviral activity against Herpes simplex virus 2 G infected in HEL cells assessed as inhibition of virus-induced cytopathicity2013European journal of medicinal chemistry, , Volume: 70Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides.
AID304884Antiviral activity against TK- VZV 07 in HEL cells after 5 days2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines.
AID216468Antiviral activity against Varicella-Zoster virus (thymidine kinase deficient) TK-(07/1)2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Bicyclic anti-VZV nucleosides: thieno analogues bearing an alkylphenyl side chain have reduced antiviral activity.
AID445340Antiviral activity against thymidine kinase deficient Varicella zoster virus 07/1 infected human HEL cells assessed as reduction in viral plaque formation after 5 days2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
2'-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743.
AID246317Effective concentration required to reduce Varicella Zoster virus YS plaque formation by using DMSO as solvent2005Bioorganic & medicinal chemistry letters, Aug-15, Volume: 15, Issue:16
Bicyclic nucleoside inhibitors of Varicella-Zoster virus: the effect of branching in the p-alkylphenyl side chain.
AID445337Ratio of Vmax to Km for Varicella zoster virus recombinant thymidine kinase2009Bioorganic & medicinal chemistry letters, Nov-15, Volume: 19, Issue:22
2'-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743.
AID588200Antiviral activity against Varicella zoster virus YS infected in HEL cells assessed as reduction in virus induced cytopathicity2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's8 (72.73)29.6817
2010's2 (18.18)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]