Compounds > xk 263
Page last updated: 2024-11-08

xk 263

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 CID446153
CHEMBL ID33647
MeSH IDM0273382

Synonyms (14)

Synonym
chembl33647 ,
(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis(naphthalen-2-ylmethyl)-1,3-diazepan-2-one
bdbm153
(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis(2-naphthylmethyl)-1,3-diazepan-2-one
[4r-(4.alpha.,5.alpha.,6.beta.,7.beta.)]-hexahydro-1,3-bis(2-naphthylmethyl)-2h-5,6-dihydroxy-4,7-dibenzyl-2h-1,3-diazepin-2-one
2h-1,3-diazepin-2-one, hexahydro-5,6-dihydroxy-1,3-bis(2-naphthalenylmethyl)-4,7-bis(phenylmethyl)-, (4r,5s,6s,7r)-
xk263
153244-86-1
[4r-(4alpha,5alpha,6beta,7beta)]-hexahydro-5,6-dihydroxy-1,3-bis[2-naphthyl-methyl]-4,7-bis(phenylmethyl)-2h-1,3-diazepin-2-one
1HVR
xk-263
(4r-(4alpha,5alpha,6beta,7beta))-hexahydro-1,3-bis(2-naphthylmethyl)-2h-5,6-dihydroxy-4,7-dibenzyl-2h-1,3-diazepin-2-one
DTXSID60165301
Q27467569

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Highly selective, preorganized inhibitors with relatively low molecular weight and high oral bioavailability were synthesized."( Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors.
Bacheler, LT; Eyermann, CJ; Hodge, CN; Jadhav, PK; Lam, PY; Meek, JL; Otto, MJ; Rayner, MM; Ru, Y; Wong, YN, 1994)		0.29
" The small size probably contributes to the observed good oral bioavailability in animals."( Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
Aldrich, PE; Bacheler, LT; Chang, CH; Confalone, PN; Daneker, WF; DeLucca, GV; Emmett, G; Eyermann, CJ; Han, Q; Hodge, CN; Holler, ER; Jadhav, PK; Klabe, RM; Kornhauser, DM; Lam, PY; Li, L; Li, R; Markwalder, JA; McHugh, RJ; Rayner, MM; Ru, Y; Seitz, SP; Sharpe, TR; Shum, L; Winslow, DL, 1996)		0.29
" Using this approach several very potent (IC90 11 nM) and orally bioavailable (F% 93-100%) compounds were discovered (21, 22)."( Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
Bacheler, LT; Cordova, B; De Lucca, GV; Erickson-Viitanen, S; Garber, S; Kim, UT; Klabe, RM; Ko, SS; Lam, GN; Liang, J; Logue, KA; Trainor, GL; Wright, MR, 1998)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HIV-1 PROTEASEHuman immunodeficiency virus 1Ki0.00030.00030.00030.0003AID977610
Chain B, HIV-1 PROTEASEHuman immunodeficiency virus 1Ki0.00030.00030.00030.0003AID977610
Gag-Pol polyproteinHuman immunodeficiency virus type 1 (BRU ISOLATE)Ki0.00030.00000.08283.3000AID1795214
Protease Human immunodeficiency virus 1Ki0.00030.00000.04433.1000AID160292; AID160474; AID163483
Protease Human immunodeficiency virus 1Ki0.00000.00000.02841.1000AID339768
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID104226Antiviral potency evaluated by measuring accumulation of viral RNA transcripts 3 days after infection of MT-2 cells with HIV-1 RF1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID160769Affinity for HIV Protease2002Journal of medicinal chemistry, Jun-20, Volume: 45, Issue:13
SMall Molecule Growth 2001 (SMoG2001): an improved knowledge-based scoring function for protein-ligand interactions.
AID339768Inhibition of HIV1 protease2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Is quantum mechanics necessary for predicting binding free energy?
AID163483Binding affinity for HIV-1 protease enzyme was measured by using fluorescent peptide substrate1998Journal of medicinal chemistry, Apr-23, Volume: 41, Issue:9
Nonpeptide cyclic cyanoguanidines as HIV-1 protease inhibitors: synthesis, structure-activity relationships, and X-ray crystal structure studies.
AID104232The antiviral potency (IC90) was assessed by measuring their effect on the accumulation of viral RNA transcripts on HIV-1 RF infected MT-2 cells1998Journal of medicinal chemistry, Apr-23, Volume: 41, Issue:9
Nonpeptide cyclic cyanoguanidines as HIV-1 protease inhibitors: synthesis, structure-activity relationships, and X-ray crystal structure studies.
AID160292Inhibition of HIV-1 protease1999Journal of medicinal chemistry, Jan-28, Volume: 42, Issue:2
Three-dimensional quantitative structure-activity relationship study on cyclic urea derivatives as HIV-1 protease inhibitors: application of comparative molecular field analysis.
AID160474Inhibitory activity against HIV protease1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID1811Experimentally measured binding affinity data derived from PDB1994Science (New York, N.Y.), Jan-21, Volume: 263, Issue:5145
Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1994Science (New York, N.Y.), Jan-21, Volume: 263, Issue:5145
Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors.
AID1795214Protease Inhibition Assay from Article 10.1021/jm9602571: \\Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.\\1996Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18
Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
[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's5 (71.43)18.2507
2000's2 (28.57)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]

Market Indicators

Research Demand Index: 12.15

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 Index12.15 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.23 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.15)

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
phosphoglycolate
phosphoglycolate: RN given refers to parent acid. 2-phosphoglycolic acid : The O-phospho derivative of glycolic acid.		2.0110carboxyalkyl phosphateEscherichia coli metabolite;
mouse metabolite
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		2.0110long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
phenethylamine
phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.		2.0110alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
benzamidine
benzamidine: RN given refers to parent cpd. benzamidine : A carboxamidine that is benzene carrying an amidino group.		2.0110benzenes;
carboxamidine		serine protease inhibitor
histidine
Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.		2.0110amino acid zwitterion;
histidine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
xylitol
xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.		2.0110
3-phenylpropylamine
3-phenylpropylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 3-aminopropyl group.		2.0110benzenes;
phenylalkylamine;
primary amino compound
1-deoxynojirimycin
1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.		2.01102-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
nitroaniline
nitroaniline: RN given refers to cpd with unspecified locant for nitro moiety. nitroaniline : A substituted aniline that carries one or more nitro groups.		2.0110
abbott 77003
Abbott 77003: a symmetry-based inhibitor of HIV-1 protease		2.0110
amprenavir
[no description available]		2.0110carbamate ester;
sulfonamide;
tetrahydrofuryl ester		antiviral drug;
HIV protease inhibitor
2-deoxy-2,3-dehydro-n-acetylneuraminic acid
2-deoxy-2,3-dehydro-N-acetylneuraminic acid: also known as NeuAc2en, but this is also synonym for another compound. 2-deoxy-2,3-dehydro-N-acetylneuraminic acid : N-Acetylneuraminic acid reduced across the 2,3-bond with loss of the hydroxy group at C-2; it is a minor component of body fluids although abundant in sialuria.		2.0110N-acetylneuraminic acids
4-fluorobenzylamine
[no description available]		2.0110
brinzolamide
brinzolamide: an antiglaucoma agent		2.0110sulfonamide;
thienothiazine		antiglaucoma drug;
EC 4.2.1.1 (carbonic anhydrase) inhibitor
a 76889
A 76889: backbone structure gvien in first source		2.0110
dmp 323
(4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one : A 1,3-diazepanone ring with two 4-(hydroxymethyl)benzyl groups as substituents at positions N-1 and N-4, two benzyl groups at C-4 and C-7, and two hydroxy groups at C-5 and C-6 respectively.		2.9140diazepanone;
ureas		anti-HIV agent;
metabolite
methanesulfonamide
[no description available]		2.0110
4-phenylbutylamine
4-phenylbutylamine: used as a drug partition into lipid bilayers in a cubic liquid-crystalline phase. 4-phenylbutylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 4-aminobutyl group.		2.0110benzenes;
phenylalkylamine;
primary amino compound
6-phosphogluconic acid
gluconic acid-6-phosphate: structure. 6-phospho-D-gluconate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of 6-phospho-D-gluconic acid.. 6-phospho-D-gluconic acid : A gluconic acid phosphate having the phosphate group at the 6-position. It is an intermediate in the pentose phosphate pathway.		2.0110gluconic acid phosphatefundamental metabolite
methotrexate
[no description available]		2.0110dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
n-acetylseryl-leucyl-asparaginyl(phenylalanyl-hydroxyethylamino-prolyl)isoleucyl-valyl methyl ester
N-acetylseryl-leucyl-asparaginyl(phenylalanyl-hydroxyethylamino-prolyl)isoleucyl-valyl methyl ester: inhibitor of HIV Protease; structure given in first source; RN given is for (S-(R*,R*)) isomer		2.0110
h 142
H 142: decapeptide inhibitor of human renin; RN given refers to all L-isomer		2.0110
h 256
H 256: heptapeptide inhibitor of pepsin		2.0110
dmp 450
DMP 450: structure in first source		2.9140
n-valyltryptophan
N-valyltryptophan: RN given refers to (L)-isomer		2.0110peptide
cp 71362
[no description available]		2.0110
arabinose
[no description available]		2.0110L-arabinoseEscherichia coli metabolite;
mouse metabolite
galactose
beta-D-galactose : A D-galactopyranose having beta-configuration at the anomeric centre.. beta-D-galactoside : Any D-galactoside having beta-configuration at its anomeric centre.		2.0110D-galactopyranoseepitope;
mouse metabolite
xv 638
XV638 : A member of the class of diazepanones that is 1,3-diazepane which is substituted by a 3-(1,3-thiazol-2-ylcarbamoyl)benzyl group at positions 1 and 3, oxo group at position 2, hydroxy groups at positions 5S and 6S, and benzyl groups at positions 4R and 7R. It is a potent HIV-1 protease inhibitor.		2.69301,3-thiazoles;
benzamides;
diazepanone;
diol;
secondary alcohol;
secondary carboxamide;
ureas		HIV protease inhibitor
phosphoramidon
phosphoramidon: a membrane metallo-endopeptidase & endothelin-converting enzyme inhibitor; thermolysin inhibitor from culture filtrate of Streptomyces tanashiensis; structure. phosphoramidon : A dipeptide isolated from the cultures of Streptomyces tanashiensis.		2.0110deoxyaldohexose phosphate;
dipeptide		bacterial metabolite;
EC 3.4.24.11 (neprilysin) inhibitor;
EC 3.4.24.71 (endothelin-converting enzyme 1) inhibitor
retinol
Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).		2.0110retinol;
vitamin A		human metabolite;
mouse metabolite;
plant metabolite
phosphonoacetohydroxamate
phosphonoacetohydroxamic acid : The hydroxamate of phosphonoacetic acid.		2.0110hydroxamic acid;
organic phosphonate
tacrolimus
Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.		2.0110macrolide lactambacterial metabolite;
immunosuppressive agent
a 76928
A 76928: a diol with C2-symmetry		2.0110
phenylalanyl-prolyl-arginine
[no description available]		2.0110oligopeptide
glycyllysine
glycyllysine: RN given refers to (L)-isomer. Gly-Lys : A dipeptide formed from glycine and L-lysine residues.		2.0110dipeptidemetabolite
leucine hydroxamate
leucine hydroxamate: RN given refers to (S)-isomer		2.0110
pepstatin
pepstatin: inhibits the aspartic protease endothiapepsin		2.0110pentapeptide;
secondary carboxamide		bacterial metabolite;
EC 3.4.23.* (aspartic endopeptidase) inhibitor
streptomyces pepsin inhibitor
[no description available]		2.4320
cp 81282
CP 81282: structure given in first source; inhibits human renin and endothiapepsin		2.0110
benzoyl-norleucyl-lysyl-arginyl-arginal
[no description available]		2.0410
ConditionIndicatedRelationship StrengthStudiesTrials