Page last updated: 2024-11-08

ic9564

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Description

IC9564: betulinic acid derivative; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID463615
CHEMBL ID137752
SCHEMBL ID14369573
MeSH IDM0377792

Synonyms (11)

Synonym
ic-9564
heptanoic acid, 3-hydroxy-4-[[8-[[(3.beta.)-3-hydroxy-28-oxolup-20(29)-en-28-yl]amino]-1-oxooctyl]amino]-6-methyl-, (3r,4s)-
174847-98-4
(3r,4s)-4-[8-[[(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]amino]octanoylamino]-3-hydroxy-6-methyl-heptanoic acid
ic9564
CHEMBL137752
(3r,4s)-4-[8-[[(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]amino]octanoylamino]-3-hydroxy-6-methylheptanoic acid
(3r,4s)-n'-(n-3beta-hydroxylup-20(29)-en-28-oyl)-8-aminooctanoyl)-4-amino-3-hydroxy-6-methylheptanoic acid
heptanoic acid, 3-hydroxy-4-((8-(((3beta)-3-hydroxy-28-oxolup-20(29)-en-28-yl)amino)-1-oxooctyl)amino)-6-methyl-, (r-(r*,s*))-
ic 9564
SCHEMBL14369573

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" These mt-QSARs offer also a good opportunity to construct drug-drug Complex Networks (CNs) that can be used to explore large and complex drug-viral species databases."( Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.
Chou, KC; González-Díaz, H; Martinez de la Vega, O; Prado-Prado, FJ; Ubeira, FM; Uriarte, E, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (57)

Assay IDTitleYearJournalArticle
AID427785Antiviral activity against HIV1 ZM197M.PB7 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID492516Antiviral activity against HIV1 by fusion assay2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID350159Antiviral activity against HIV1 NL4-3 infected in human MT4 cells assessed as p24 antigen level after 4 days by ELISA2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents.
AID427781Antiviral activity against HIV1 WITO4160.33 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID683336Antiviral activity against HIV1 in human TZM-bl cells assessed as viral infectivity by luciferase assay2012European journal of medicinal chemistry, Oct, Volume: 56Anti-HIV activity of semisynthetic derivatives of andrographolide and computational study of HIV-1 gp120 protein binding.
AID427601Antiviral activity against HIV1 Q769.d22 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427791Cytotoxicity against human TZM-bl cells at 15 uM after 2 days by trypan blue exclusion assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427799Inhibition of V3-speciifc monoclonal antibody 2G12 binding to HIV1 3B gp120 by ELISA-based competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427801Inhibition of V3-speciifc monoclonal antibody 2G12 binding to HIV1 Ba-L gp120 by ELISA-based competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID439732Ratio of IC50 for HIV2 KR X3 infected in human TZM-b1 cells to IC50 for HIV1 NL4-3 infected in human TZM-b1 cells2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors.
AID1706899Anti-HIV-1 activity against HIV1 NL4-3 infected in human HeLa expressing CD4/CCR5/beta-gal assessed as inhibition of syncytium formation incubated for 2 days by MAGI assay2020Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24
Triterpenoid-Mediated Inhibition of Virus-Host Interaction: Is Now the Time for Discovering Viral Entry/Release Inhibitors from Nature?
AID1873271Antiviral activity against HIV-1 NL4-3(X4) infected in human TZM-bl cells assessed as reduction in viral replication2022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Design, synthesis, and bio-evaluation of novel triterpenoid derivatives as anti-HIV-1 compounds.
AID427605Antiviral activity against HIV1 HXB2 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID621520Inhibition of human 20S proteasome chymotrypsin-like activity using Suc-Leu-Leu-Val-Tyr-AMC fluorogenic substrate by fluorimetry2011Bioorganic & medicinal chemistry letters, Oct-01, Volume: 21, Issue:19
New betulinic acid derivatives as potent proteasome inhibitors.
AID427788Antiviral activity against HIV1 ZM109F.PB4 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427786Antiviral activity against HIV1 ZM214M.PL15 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427604Antiviral activity against HIV1 NL4-3 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427784Antiviral activity against HIV1 Du422.1 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427599Antiviral activity against HIV1 Q168.a2 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID439729Cytotoxicity against human TZM-b1 cells after 2 days2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors.
AID427776Antiviral activity against HIV1 QH0515.1 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427606Antiviral activity against HIV1 5768.4 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID392513Antiviral activity against HIV12009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.
AID81086Anti HIV-1 activity against the virus NL4-3 using fusion assay2002Journal of medicinal chemistry, Sep-12, Volume: 45, Issue:19
Anti-AIDS agents 49. Synthesis, anti-HIV, and anti-fusion activities of IC9564 analogues based on betulinic acid.
AID427797Inhibition of V3-speciifc monoclonal antibody 447-52D binding to HIV1 3B gp120 by ELISA-based competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID439728Antiviral activity against HIV2 KR X3 infected in human TZM-b1 cells assessed as reduction in luciferase activity after 2 days by luciferase reporter gene assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors.
AID427603Antiviral activity against HIV1 Q842.d12 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427789Antiviral activity against HIV1 CAP.2.00.G3 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427803Inhibition of HIV1 3B gp120/CD4 complex binding to CCR5 expressing HOS cells at 5 mg/ml after 1 hr by competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427783Antiviral activity against HIV1 Du151.2 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID271062Cytotoxicity against COS-TZM fused cells2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Anti-AIDS agents 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents.
AID439727Antiviral activity against HIV1 NL4-3 infected in human TZM-b1 cells assessed as reduction in luciferase activity after 2 days by luciferase reporter gene assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors.
AID350163Therapeutic index, ratio of CC50 for human MT4 cells to EC50 for HIV1 NL4-32009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents.
AID427778Antiviral activity against HIV1 TRO.11 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427600Antiviral activity against HIV1 Q461.e2 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427796Ratio of inhibition of HIV1 NH4-3 envelope glycoprotein 120-mediated membrane fusion to inhibition of HIV1 (isolate YU2) envelope glycoprotein 120-mediated membrane fusion2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427602Antiviral activity against HIV1 Q259.d2.17 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427787Antiviral activity against HIV1 ZM55F.PB28a infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID1873270Antiviral activity against HIV-1 YU2 (R4) infected in human TZM-bl cells assessed as reduction in viral replication2022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Design, synthesis, and bio-evaluation of novel triterpenoid derivatives as anti-HIV-1 compounds.
AID427777Antiviral activity against HIV1 SS1196.1 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID271061Inhibition of membrane fusion between HIV1 NL4-3 envelope gene expressing COS cells and TZM cells2006Journal of medicinal chemistry, Sep-07, Volume: 49, Issue:18
Anti-AIDS agents 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents.
AID427790Antiviral activity against HIV1 CAP244.2.00.D3 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427800Inhibition of V3-speciifc monoclonal antibody 447-52 binding to HIV1 Ba-L gp120 by ELISA-based competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID1873272Antiviral activity against HIV-1 89.6 infected in human TZM-bl cells assessed as reduction in viral replication2022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Design, synthesis, and bio-evaluation of novel triterpenoid derivatives as anti-HIV-1 compounds.
AID492515Antiviral activity against HIV1 by MAGI assay2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID81085Anti HIV-1 activity against the virus NL4-3 using MAGI assay2002Journal of medicinal chemistry, Sep-12, Volume: 45, Issue:19
Anti-AIDS agents 49. Synthesis, anti-HIV, and anti-fusion activities of IC9564 analogues based on betulinic acid.
AID1873273Cytotoxicity against human TZM-bl cells assessed as reduction in cell viability by CellTitre-Glo assay2022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Design, synthesis, and bio-evaluation of novel triterpenoid derivatives as anti-HIV-1 compounds.
AID427792Cytotoxicity against human TZM-bl cells after 2 days by trypan blue exclusion assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427607Antiviral activity against HIV1 6535.3 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427780Antiviral activity against HIV1 REJO4541.67 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427798Inhibition of V3-speciifc monoclonal antibody 39F binding to HIV1 3B gp120 by ELISA-based competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID350162Cytotoxicity against human MT4 cells by XTT assay2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents.
AID427779Antiviral activity against HIV1 RHPA4259.7 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID1873274Selectivity index, ratio of CC50 for human TZM-bl cells to IC50 for IC50 for antiviral activity against HIV-1 89.6 infected in human TZM-bl cells2022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Design, synthesis, and bio-evaluation of novel triterpenoid derivatives as anti-HIV-1 compounds.
AID427782Antiviral activity against HIV1 Du123.6 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427598Antiviral activity against HIV1 Q23.71 infected in human TZM-b1 cells assessed as inhibition of viral infection after 2 days postinfection by luciferase reporter gene assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
AID427802Inhibition of HIV1 Ba-L gp120/CD4 complex binding to CCR5 expressing HOS cells at 5 mg/ml after 1 hr by competitive binding assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's9 (64.29)29.6817
2010's3 (21.43)24.3611
2020's2 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.73

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 Index11.73 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]