Compounds > macrocarpal a
Page last updated: 2024-12-08

macrocarpal a

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Description

macrocarpal A: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID454457
CHEMBL ID396609
SCHEMBL ID96208
MeSH IDM0508709

Synonyms (17)

Synonym
macrocarpal a
5-[(1r)-1-[(1ar,4r,4ar,7s,7as,7br)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methyl-butyl]-2,4,6-trihydroxy-benzene-1,3-dicarbaldehyde
132951-90-7
5-[(1r)-1-((11s,7r)-7-hydroxy-3,3,7,11-tetramethyltricyclo[6.3.0.0<2,4>]undec-11-yl)-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
CHEMBL396609
5-[(1r)-1-[(1ar,4r,4ar,7s,7as,7br)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
5-((1r)-1-((11s,7r)-7-hydroxy-3,3,7,11-tetramethyltricyclo(6.3.0.0(2,4))undec-11-yl)-3-methylbutyl)-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
SCHEMBL96208
DTXSID70157878
AKOS032948754
2,4,6-trihydroxy-5-[(1r)-1-[(1abeta,4r,4abeta,7aalpha,7bbeta)-1,1,4,7-tetramethyl-4beta-hydroxydecahydro-1h-cyclopro
macrocarpala
5-(1r)-1-(1ar,4r,4ar,7s,7as,7br)-ecahydro-4-ydroxy-1,1,4,7-etramethyl-1h-ycloprop[e]zulen-7-l]-3-ethylbutyl]-2,4,6-rihydroxy-1,3-enzenedicarboxaldehde; 10-pi-ucarobustol f
CS-0023952
1,3-benzenedicarboxaldehyde, 5-[(1r)-1-[(1ar,4r,4ar,7s,7as,7br)-decahydro-4-hydroxy-1,1,4,7-tetramethyl-1h-cycloprop[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxy-
FS-10306
HY-N3346
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (44)

Assay IDTitleYearJournalArticle
AID305378Ratio of permeability from basolateral to apical side over apical to basolateral side of human Caco-2 cells at 30 uM2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID355163Inhibition of Streptococcus sobrinus glucosyltransferase assessed as blockade of adherent water insoluble glucan synthesis at 1 ug/mL1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID355154Antibacterial activity against Streptococcus sobrinus B13 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID355157Antibacterial activity against Prevotella melaninogenica 25845 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID1586735Inhibition of calf thymus topoisomerase-1 assessed as reduction in cleavage complex formation by measuring nicked form DNA level using supercoiled pBR322 DNA as substrate after 30 mins by agarose gel electrophoresis assay (Rvb = 47%)2018Journal of natural products, 12-28, Volume: 81, Issue:12
Eucalypglobulusals A-J, Formyl-Phloroglucinol-Terpene Meroterpenoids from Eucalyptus globulus Fruits.
AID305377Apparent permeability from basolateral to apical side of human Caco-2 cells at 100 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305375Apparent permeability from basolateral to apical side of human Caco-2 cells at 30 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305376Apparent permeability from basolateral to apical side of human Caco-2 cells at 50 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305373Apparent permeability from apical to basolateral side of human Caco-2 cells at 50 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305391Drug level in Caco-2 cells assessed as total recovery rate at 50 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305384Drug level in Caco-2 cells assessed as intracellular accumulation at 50 uM after 60 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID1315357Cytotoxicity against human HL60 cells assessed as reduction in cell viability after 72 hrs by MTT assay2016Journal of natural products, 05-27, Volume: 79, Issue:5
Eucarobustols A-I, Conjugates of Sesquiterpenoids and Acylphloroglucinols from Eucalyptus robusta.
AID1586738Inhibition of calf thymus topoisomerase-1-mediated relaxed pBR322 DNA unwinding at 25 uM preincubated with DNA for 10 mins followed by enzyme addition and measured after 30 mins by agarose gel electrophoresis assay2018Journal of natural products, 12-28, Volume: 81, Issue:12
Eucalypglobulusals A-J, Formyl-Phloroglucinol-Terpene Meroterpenoids from Eucalyptus globulus Fruits.
AID305379Ratio of permeability from basolateral to apical side over apical to basolateral side of human Caco-2 cells at 50 uM2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID1639217Immunosuppressive activity in BALB/c mouse lymph node cells assessed as inhibition of concanavalin A stimulated T-cell proliferation measured after 48 hrs by CCK8 assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Phloroglucinols with Immunosuppressive Activities from the Fruits of Eucalyptus globulus.
AID1639218Stimulation index, ratio of CC50 for BALB/c mouse lymph node cells to IC50 for immunosuppressive activity in BALB/c mouse lymph node cells assessed as inhibition of concanavalin A stimulated T-cell proliferation2019Journal of natural products, 04-26, Volume: 82, Issue:4
Phloroglucinols with Immunosuppressive Activities from the Fruits of Eucalyptus globulus.
AID1586736Inhibition of supercoiled pBR322 DNA binding to calf thymus topoisomerase-1 after 0.5 hrs by agarose gel electrophoresis assay2018Journal of natural products, 12-28, Volume: 81, Issue:12
Eucalypglobulusals A-J, Formyl-Phloroglucinol-Terpene Meroterpenoids from Eucalyptus globulus Fruits.
AID305392Drug level in Caco-2 cells assessed as total recovery rate at 50 uM after 120 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID355159Antibacterial activity against Capnocytophaga ochracea 33596 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID355160Antibacterial activity against Fusobacterium nucleatum 25586 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID305390Drug level in Caco-2 cells assessed as total recovery rate at 50 uM after 60 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305380Ratio of permeability from basolateral to apical side over apical to basolateral side of human Caco-2 cells at 100 uM2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID355158Antibacterial activity against Prevotella intermedia 25611 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID1586737Inhibition of calf thymus topoisomerase-1-mediated supercoiled pBR322 DNA unwinding at 25 uM preincubated with DNA for 10 mins followed by enzyme addition and measured after 30 mins by agarose gel electrophoresis assay2018Journal of natural products, 12-28, Volume: 81, Issue:12
Eucalypglobulusals A-J, Formyl-Phloroglucinol-Terpene Meroterpenoids from Eucalyptus globulus Fruits.
AID355155Antibacterial activity against Actinomyces viscosus 15987 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID305372Apparent permeability from apical to basolateral side of human Caco-2 cells at 30 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305394Drug level in Caco-2 cells assessed as total recovery rate at 50 uM after 180 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID702540Inhibition of c-MET assessed as inhibition of HGF-induced phosphorylation at 5 uM by Western blotting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Potent HGF/c-Met axis inhibitors from Eucalyptus globulus: the coupling of phloroglucinol and sesquiterpenoid is essential for the activity.
AID355151Antibacterial activity against Streptococcus mutans Ingbritt by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID355161Inhibition of Streptococcus sobrinus glucosyltransferase assessed as blockade of adherent water insoluble glucan synthesis at 100 ug/mL1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID1315358Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 72 hrs by SRB assay2016Journal of natural products, 05-27, Volume: 79, Issue:5
Eucarobustols A-I, Conjugates of Sesquiterpenoids and Acylphloroglucinols from Eucalyptus robusta.
AID355162Inhibition of Streptococcus sobrinus glucosyltransferase assessed as blockade of adherent water insoluble glucan synthesis at 10 ug/mL1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID305383Drug level in Caco-2 cells assessed as intracellular accumulation at 50 uM after 30 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305389Drug level in Caco-2 cells assessed as total recovery rate at 50 uM after 30 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID355153Antibacterial activity against Streptococcus sobrinus 6715 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID355152Antibacterial activity against Streptococcus mutans LA7 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID305386Drug level in Caco-2 cells assessed as intracellular accumulation at 50 uM after 120 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID1639216Cytotoxicity against BALB/c mouse lymph node cells assessed as reduction in cell viability measured after 48 hrs by CCK8 assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Phloroglucinols with Immunosuppressive Activities from the Fruits of Eucalyptus globulus.
AID305393Drug level in Caco-2 cells assessed as total recovery rate at 50 uM after 150 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305374Apparent permeability from apical to basolateral side of human Caco-2 cells at 100 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID355156Antibacterial activity against Porphyromonas gingivalis 33277 by broth dilution method1996Journal of natural products, Sep, Volume: 59, Issue:9
Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.
AID305387Drug level in Caco-2 cells assessed as intracellular accumulation at 50 uM after 150 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305385Drug level in Caco-2 cells assessed as intracellular accumulation at 50 uM after 90 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
AID305388Drug level in Caco-2 cells assessed as intracellular accumulation at 50 uM after 180 mins2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's2 (22.22)29.6817
2010's6 (66.67)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: 12.63

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 Index12.63 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (11.11%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phloroglucinol
Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.		4.3541benzenetriol;
phenolic donor		algal metabolite
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		2.0310aromatic ether;
nitrile;
polyether;
tertiary amino compound
iodoacetamide
[no description available]		2.0310
thymol
Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.		1.9910monoterpenoid;
phenols		volatile oil component
oleanolic acid
[no description available]		2.1310hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
ethidium bromide
[no description available]		2.1710organic bromide saltgeroprotector;
intercalator;
trypanocidal drug
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.1710delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
etoposide
[no description available]		2.1710beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.0310D-glucopyranoseepitope;
mouse metabolite
epigallocatechin gallate
epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.		1.9910flavans;
gallate ester;
polyphenol		antineoplastic agent;
antioxidant;
apoptosis inducer;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent;
plant metabolite
macrocarpal b
macrocarpal B: structure in first source		3.360sesquiterpenoid
bucladesine
macrocarpal C: structure in first source		2.9640sesquiterpenoid
gamma-sitosterol
clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.		2.03103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite
sesquiterpenes
[no description available]		4.3541
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		2.0310
stigmasterol
stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.		2.03103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols;
stigmastane sterol		plant metabolite
cyclosporine
ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF		2.2110homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite
verlukast
verlukast: LTD4 receptor antagonist		2.0310
cypellocarpin c
cypellocarpin C: isolated from Eucalyptus cypellocarpa; structure in first source		2.4420
jensenone
jensenone: a marsupial antifeedant from Eucalyptus; structure in first source		2.0710
ConditionIndicatedRelationship StrengthStudiesTrials