Compounds > costatolide
Page last updated: 2024-12-08

costatolide

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

Description

(-)-calanolide B : An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase. [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]

FloraRankFlora DefinitionFamilyFamily Definition
CalophyllumgenusA plant genus of the family CLUSIACEAE. Members contain costatolide, calanolides and 4-phenylfuranocoumarins (FUROCOUMARINS).[MeSH]Calophyllaceae[no description available]
Calophyllum brasiliensespecies[no description available]Calophyllaceae[no description available]
Calophyllum lanigerumspecies[no description available]Calophyllaceae[no description available]

Cross-References

ID SourceID
PubMed CID461128
CHEMBL ID7187
CHEBI ID65553
SCHEMBL ID8927756
MeSH IDM0333146

Synonyms (19)

Synonym
(10s,11r,12s)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-6h,10h-dipyrano[2,3-f;2'',3''-h]chromen-2-one
bdbm50050431
909-14-8
costatolide
costatolide (calophyllum)
(-)-calanolide b
2h,6h,10h-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one,11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-,(10s,11r,12s)-
nsc 661122
chebi:65553 ,
CHEMBL7187 ,
2h,6h,10h-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one,11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-,(10s,11r,12s)-
(+)-(10s,11r,12s)-10,11-trans-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2h,6h-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one
(10s,11r,12s)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2h,6h,10h-dipyrano[2,3-f:2',3'-h]chromen-2-one
(10s,11r,12s)-11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2h,6h,10h-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one
SCHEMBL8927756
NIDRYBLTWYFCFV-PZROIBLQSA-N
12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2h,6h,10h-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one
DTXSID50920087
Q27134006
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
HIV-1 reverse transcriptase inhibitorAn entity which inhibits the activity of HIV-1 reverse transcriptase.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from 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]

Drug Classes (4)

ClassDescription
delta-lactoneA lactone having a six-membered lactone ring.
cyclic etherAny ether in which the oxygen atom forms part of a ring.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
organic heterotetracyclic compound
[compound class information is derived from 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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)0.84500.00011.076810.0000AID355049; AID355050
Protease Human immunodeficiency virus 1IC50 (µMol)91.75000.00010.22487.3200AID199678; AID199679
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID106919Anti-HIV activity against HIV-I IIIB strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID106887Anti-HIV activity against HIV-I H112-2 strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID355022Antiviral activity against HIV1 infected in human H9 cells assessed as effect on virus-induced cytopathic effect by tetrazolium/formazan assay1996Journal of natural products, Aug, Volume: 59, Issue:8
New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii.
AID106915Anti-HIV activity against HIV-I H112-2 strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID56388Percent inhibition against DNA polymerase beta at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199684Percent inhibition against TIBO-resistant HIV-1 RT Nucleic Acid polymerase at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199676Inhibitory activity against HIV-2 RT Nucleic Acid polymerase; IA=inactive1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199677Percent inhibition against HIV-2 RT Nucleic Acid polymerase at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID106914Anti-HIV activity against HIV-I G910-6 strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID235020Ratio of inhibitory concentration to that of effective concentration for protection of CEM-SS cells from cytopathic effects of HIV-1 (RF strain)1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B.
AID166867Percent inhibition against RNA polymerase at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID106918Anti-HIV activity against HIV-I H112-2 strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID46371Anti-HIV activity against HIV-I RFII strain in CEM cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199525Percent inhibition against Avian Myeloblastosis Virus Reverse Transcriptase (AMV RT) at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID46060Using the XTT assay for cell viability, inhibitory concentration to protect human lymphoblastoid CEM-SS cells from the cytopathic effects of HIV-1 (RF strain) was determined1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B.
AID199682Percent inhibition against DNA -dependent DNA polymerase (DDDP) of HIV-1 RT Nucleic Acid polymerase at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID397594Therapeutic index, ratio of cytotoxicity against human CEM-SS cells to EC50 for HIV1 RF2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID53669Inhibitory activity against DNA polymerase alpha; IA=inactive1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199678Inhibitory activity against DNA -dependent DNA polymerase (DDDP) of HIV-1 RT Nucleic Acid polymerase1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID106916Anti-HIV activity against HIV-I A17 strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID56384Percent inhibition against DNA polymerase alpha at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID56386Inhibitory activity against DNA polymerase beta1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID45710Using the XTT assay for cell viability, effective concentration to protect human lymphoblastoid CEM-SS cells from the cytopathic effects of HIV-1 (RF strain) was determined1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B.
AID166866Inhibitory activity against RNA polymerase; IA=inactive1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID397593Antiviral activity against HIV1 RF 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.
AID199681Inhibitory activity against TIBO-resistant HIV-1 RT Nucleic Acid polymerase; IA=inactive1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID355023Cytotoxicity against human H9 cells1996Journal of natural products, Aug, Volume: 59, Issue:8
New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii.
AID355049Inhibition of RNA dependent DNA polymerase activity of HIV1 recombinant reverse transcriptase p66/p511996Journal of natural products, Sep, Volume: 59, Issue:9
Specific inhibition of human immunodeficiency virus type 1 reverse transcriptase mediated by soulattrolide, a coumarin isolated from the latex of calophyllum teysmannii.
AID355024Therapeutic index, ratio of IC50 for human H9 cells to EC50 for HIV11996Journal of natural products, Aug, Volume: 59, Issue:8
New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii.
AID106917Anti-HIV activity against HIV-I G910-6 strain in MT2 cell line1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199683Percent inhibition against RNA-dependent DNA polymerase (RDDP) of HIV-1 RT Nucleic Acid polymerase at dose 200 ug/mL1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199679Inhibitory activity against RNA-dependent DNA polymerase (RDDP) of HIV-1 RT Nucleic Acid polymerase1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID199522Inhibitory activity against Avian Myeloblastosis Virus Reverse Transcriptase (AMV RT); IA=inactive1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers.
AID355050Inhibition of DNA dependent DNA polymerase activity of HIV1 recombinant reverse transcriptase p66/p511996Journal of natural products, Sep, Volume: 59, Issue:9
Specific inhibition of human immunodeficiency virus type 1 reverse transcriptase mediated by soulattrolide, a coumarin isolated from the latex of calophyllum teysmannii.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (80.00)18.2507
2000's1 (20.00)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: 12.40

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 Index12.40 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
stavudine
Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase		3.110dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
zalcitabine
Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.		3.520pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
nitidine chloride
[no description available]		3.110
nigericin
Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.		3.110polycyclic etherantibacterial agent;
antimicrobial agent;
bacterial metabolite;
potassium ionophore
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		3.520azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
lamivudine
[no description available]		3.110monothioacetal;
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
kynostatin 272
kynostatin 272: structure given in first source; contains allophenylnorstatine as a transition-state mimic		3.110peptide
calanolide a
calanolide A: NSC 661122 and costatolide are isomers; a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum (Clusiaceae); structure in first source. (+)-calanolide A : An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10R,11S,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.		4.0140cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite
kynostatin 227
kynostatin 227: structure given in first source; contains allophenylnorstatine as a transition-state mimic		3.110
lodenosine
lodenosine: anti-HIV nucleoside analog, the flourine atom on lodenosine is located at 2-arabinoside location, while 2'-fluoro-2',3'-dideoxyadenosine has the flourine residue at the 2-ribose sugar location		3.110
zidovudine triphosphate
[no description available]		1.9910
12-deoxyphorbol 13-acetate
[no description available]		3.110phorbol estermetabolite
michellamine c
michellamine A: atropisomeric naphthylisoquinoline anti-HIV cytopathic alkaloid dimers; from tropical plant Ancistrocladus abbreviatus; structure given in first source. michellamine A : A dimeric isoquinoline alkaloid isolated from Ancistrocladus abbreviatus and has been shown to exhibit anti-HIV activity.		3.110
fumarprotocetraric acid
fumarprotocetraric acid: RN given refers to (E)-isomer; structure given in first source		3.110carbonyl compound
guttiferone a
guttiferone A: antibacterial from Clusiaceae family; structure in first source		3.110
pepstatin
pepstatin: inhibits the aspartic protease endothiapepsin		3.110pentapeptide;
secondary carboxamide		bacterial metabolite;
EC 3.4.23.* (aspartic endopeptidase) inhibitor
indigo carmine
3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.		3.110
didanosine
Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		3.110purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
conocurvone
conocurvone: a trimeric naphthoquinone derivative; extracted from Conospermum incurvum; structure given in first source		3.110organic heterotricyclic compound;
organooxygen compound
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		02.3920