Page last updated: 2024-12-08

michellamine c

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Description

michellamine A: atropisomeric naphthylisoquinoline anti-HIV cytopathic alkaloid dimers; from tropical plant Ancistrocladus abbreviatus; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

michellamine A : A dimeric isoquinoline alkaloid isolated from Ancistrocladus abbreviatus and has been shown to exhibit anti-HIV activity. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID454909
CHEMBL ID295292
SCHEMBL ID2041331
MeSH IDM0195770

Synonyms (15)

Synonym
143168-23-4
(1r,3r)-5-[3-[4-[(1r,3r)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methyl-2-naphthyl]-4-hydroxy-5-methoxy-7-methyl-1-naphthyl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
5,5-(1,1'-dihydroxy-8-8'-dimethoxy-6,6'-dimethyl[2,2'-binaphthalene-4,4'-diyl)bis[1,2,3,4-tetrahydro-1,3-dimethyl-6,8-isoquinolinediol], (1r,3r,5r,1'r,3'r,5'r)
michellamine c
NSC649324 ,
michellamine a
NSC650898 ,
(1r,3r)-5-[3-[4-[(1r,3r)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methylnaphthalen-2-yl]-4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
CHEMBL295292
5,5-(1,1'-dihydroxy-8-8'-dimethoxy-6,6'-dimethyl(2,2'-binaphthalene-4,4'-diyl)bis(1,2,3,4-tetrahydro-1,3-dimethyl-6,8-isoquinolinediol), (1r,3r,5r,1'r,3'r,5'r)
michellamine
SCHEMBL2041331
DTXSID50162329
bdbm50058296
Q6836897
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (60)

Assay IDTitleYearJournalArticle
AID156043Cytotoxicity was measured against PMCs/HIV-1(Ba-L)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID9465Anti -HIV activity was measured against AA5/HIV-1(IIIB)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID44604Anti -HIV activity was measured against C-344/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45358Anti-HIV activity was measured against HIV-1 Lymphotropic MCK clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID46005Anti -HIV activity was measured against 174*CEM/HIV-1(IIIB)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45354Anti -HIV activity was measured against CEM-SS/HIV-1 (NIH-DZ)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45372Anticytopathic activity was measured against HIV-2(CBL-20 strain) in CEM-SS human lymphoblastoid target cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID403974Antiviral activity against HIV1 G9106 infected in human MT2 cells1997Journal of natural products, Jul, Volume: 60, Issue:7
Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis.
AID1187987Antimicrobial activity against Escherichia coli DH5[alpha] at 1.95 to 125 ug/ml by liquid culture microtitre plate assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID45371Anticytopathic activity was measured against HIV-1(RF strain) in CEM-SS human lymphoblastoid target cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID397756Therapeutic index, ratio of cytotoxicity against human CEM-SS cells to EC50 for HIV12001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID45364Anti-HIV activity was measured against HIV-1,IIIB laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID106894Anti-HIV activity was measured against drug resistant HIV-1 A17 in MT-2 cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID46450Cytotoxicity was measured against CEM-SS/HIV-1 (RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID106926Cytotoxicity was measured against MT-2/HIV-1(RF).1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID1187983Inhibition of MraY in Staphylococcus aureus membranes at 500 uM by continuous fluorescence assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID44665Anti -HIV activity was measured against C8166/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45367Anti-HIV activity was measured against HIV-2 CBL-20 laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45363Anti-HIV activity was measured against HIV-1 Promonocytropic TPI clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45361Anti-HIV activity was measured against HIV-1 Promonocytropic MN clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID106888Anti -HIV activity was measured against MT-2/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID100083Cytotoxicity was measured against LDV-7/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45362Anti-HIV activity was measured against HIV-1 Promonocytropic SKI clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID106895Anti-HIV activity was measured against drug resistant HIV-1 G9106 in MT-2 cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID403973Antiviral activity against HIV1 A17 infected in human MT2 cells1997Journal of natural products, Jul, Volume: 60, Issue:7
Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis.
AID44805Cytotoxicity was measured against C8166/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID1187984Inhibition of MraY in Micrococcus flavus membranes at 500 uM by continuous fluorescence assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID45359Anti-HIV activity was measured against HIV-1 Lymphotropic PM16 clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID154761Cytotoxicity was measured against PBLs/HIV-1 (WEJO)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID155914Anti -HIV activity was measured against PMCs/HIV-1(Ba-L)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID403971Cytotoxicity against human CEM-SS cells1997Journal of natural products, Jul, Volume: 60, Issue:7
Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis.
AID403970Antiviral activity against HIV1 RF infected in human CEM-SS cells1997Journal of natural products, Jul, Volume: 60, Issue:7
Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis.
AID45370Anti-HIV activity was measured against HIV-2 ROD strain laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID1187989Inhibition of recombinant MraY overexpressed in Escherichia coli membranes at 500 uM after 30 mins by radiochemical assay in presence of [14C-D-Ala]-UDPMurNAc-pentapeptide2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID1187986Antimicrobial activity against Bacillus subtilis W23 by liquid culture microtitre plate assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID1187993Inhibition of recombinant Escherichia coli MurG at 500 ug/ml after 30 mins by radiochemical assay in presence of [3H]-UDPGlcNAc2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID1187988Inhibition of recombinant MraY overexpressed in Escherichia coli membranes at 100 uM after 30 mins by radiochemical assay in presence of [14C-D-Ala]-UDPMurNAc-pentapeptide2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID9466Cytotoxicity was measured against AA5/HIV-1(IIIB)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45369Anti-HIV activity was measured against HIV-2 NIH-DZ strain laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID106927Cytotoxicity was measured against MT-2/HIV-2(NIH-DZ)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID100082Anti -HIV activity was measured against LDV-7/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID397755Antiviral activity against HIV1 in human CEM-SS cells assessed as inhibition of virus-induced cytopathic effect2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID1187982Inhibition of MraY in Pseudomonas aeruginosa membranes at 500 uM by continuous fluorescence assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID45355Anti -HIV activity was measured against CEM-SS/HIV-1 (RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID46564Cytotoxicity was measured against 174*CEM/HIV-1(IIIB)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45357Anti-HIV activity was measured against HIV-1 Lymphotropic G clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID1187991Antimicrobial activity against Micrococcus flavus at 1.95 to 125 ug/ml by liquid culture microtitre plate assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID46449Cytotoxicity was measured against CEM-SS/HIV-1 (NIH-DZ)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID44605Cytotoxicity was measured against C-344/HIV-1(RF)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID154636Anti -HIV activity was measured against PBLs/HIV-1 (WEJO)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID1187977Inhibition of recombinant MraY overexpressed in Escherichia coli membranes by continuous fluorescence assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID45360Anti-HIV activity was measured against HIV-1 Promonocytropic 214 clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID106889Anti -HIV activity was measured against MT-2/HIV-2(NIH-DZ)1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID1187978Inhibition of MraY in Bacillus subtilis membranes by continuous fluorescence assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID1187990Antimicrobial activity against Pseudomonas putida ATCC 33015 at 1.95 to 125 ug/ml by liquid culture microtitre plate assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.
AID403972Antiviral activity against HIV1 OC100 infected in human CEM-SS cells1997Journal of natural products, Jul, Volume: 60, Issue:7
Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis.
AID45365Anti-HIV activity was measured against HIV-1,LAV laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45368Anti-HIV activity was measured against HIV-2 MS laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45356Anti-HIV activity was measured against HIV-1 Lymphotropic 205 clinical isolates in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
AID45366Anti-HIV activity was measured against HIV-1,RF laboratory strains in CEM-SS cells1994Journal of medicinal chemistry, Jun-10, Volume: 37, Issue:12
Anti-HIV michellamines from Ancistrocladus korupensis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's10 (58.82)18.2507
2000's2 (11.76)29.6817
2010's5 (29.41)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: 11.78

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 Index11.78 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.56%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]