Compounds > bromophycolide a
Page last updated: 2024-11-13

bromophycolide a

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

Description

bromophycolide A: from Fijian red alga Callophycus serratus; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bromophycolide A : A diterpenoid that is a macrolide isolated from the Fijian red alga Callophycus serratus. It has been found to exhibit moderate cytotoxicity against several human tumour cell lines via specific apotopic cell death. It also displays anti-HIV, antibacterial, antifungal and antimalarial 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 CID21778345
CHEMBL ID1257967
CHEBI ID65525
SCHEMBL ID12376420
MeSH IDM0500221

Synonyms (7)

Synonym
chebi:65525 ,
CHEMBL1257967
(9s,12s,13r,15as,16s)-13,16-dibromo-9-(2-bromopropan-2-yl)-3,12-dihydroxy-12,15a,19-trimethyl-1,9,10,11,12,13,14,15,15a,16,17,18-dodecahydro-7h-6,2-(metheno)-8-benzoxacycloheptadecin-7-one
bromophycolide a
SCHEMBL12376420
Q27133974
(7s,8s,11r,12s,15s)-7,11-dibromo-15-(2-bromopropan-2-yl)-12,21-dihydroxy-4,8,12-trimethyl-16-oxatricyclo[16.3.1.03,8]docosa-1(21),3,18(22),19-tetraen-17-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (6)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimalarialA drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
anti-HIV agentAn antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
[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 (5)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
organobromine compoundA compound containing at least one carbon-bromine bond.
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
diterpenoidAny terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
macrolideA macrocyclic lactone with a ring of twelve or more members derived from a polyketide.
[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]

Bioassays (56)

Assay IDTitleYearJournalArticle
AID777540Drug metabolism in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID1423556Cytotoxicity against human HL60 cells after 48 hrs by MTT assay2018Journal of natural products, 11-26, Volume: 81, Issue:11
Halogenated Meroditerpenoids from a South Pacific Collection of the Red Alga Callophycus serratus.
AID777536Half life in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777551AUC in BALB/c mouse at 23 mg/kg, iv after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777567Antimalarial activity against Plasmodium yoelii infected in Swiss Webster mouse assessed as reduction of parasitemia at 5 mg/kg, ip qd administered on day 2 to 5 by Hoechst 33342 staining-based FACS analysis (Rvb = 32 +/- 2%)2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777519Metabolic stability in human liver microsomes assessed as formation of metabolite M5 at 10 uM by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID1890670Antiviral activity against SARS-CoV-2 isolate USA-WA1/2020 infected in Calu-3 cells at 1 uM preincubated for 24 hrs followed by viral infection and measured after 48 hrs by Hoechst 33342 staining based microscopic method2022Journal of natural products, 03-25, Volume: 85, Issue:3
Marine Natural Products as Leads against SARS-CoV-2 Infection.
AID1890671Antiviral activity against SARS-CoV-2 isolate USA-WA1/2020 infected in Calu-3 cells preincubated for 24 hrs followed by viral infection and measured after 48 hrs by Hoechst 33342 staining based microscopic method2022Journal of natural products, 03-25, Volume: 85, Issue:3
Marine Natural Products as Leads against SARS-CoV-2 Infection.
AID777563Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in erythrocytes assessed as parasite growth inhibition after 72 hrs by SYBR green I staining-based fluorescence assay2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777518Metabolic stability in human Liver S9 fraction assessed as formation of metabolite M5 at 10 uM by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777552AUC in BALB/c mouse at 23 mg/kg, ip after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777537Drug metabolism in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777520Metabolic stability in human liver S9 fraction assessed as formation of metabolite M4 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777557Elimination rate constant in BALB/c mouse at 23 mg/kg, iv after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777545Metabolic stability in mouse serum at 150 uM after 24 hrs by HPLC analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777542Metabolic stability in human liver S9 fraction at 10 uM after 4 hrs by LC-MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777532Intrinsic clearance in human liver microsomes at 10 uM after 24 hrs by LC-MS analysis in absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777522Metabolic stability in human liver S9 fraction assessed as formation of metabolite M2 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777564Antimalarial activity against Plasmodium yoelii infected in Swiss Webster mouse assessed as reduction of parasitemia at 10 mg/kg, ip qd after 48 hrs by Hoechst 33342 staining-based FACS analysis relative to control2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777527Metabolic stability in human liver microsomes assessed as formation of metabolite M1 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777543Metabolic stability in human liver microsomes at 10 uM after 4 hrs by LC-MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID516793Antimicrobial activity against methicillin-resistant Staphylococcus aureus2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Unusual antimalarial meroditerpenes from tropical red macroalgae.
AID777530Metabolic stability in human liver microsomes assessed as compound remaining at 10 uM after 24 hrs by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777565Antimalarial activity against Plasmodium yoelii infected in Swiss Webster mouse assessed as reduction of parasitemia at 10 mg/kg, ip qd after 24 hrs by Hoechst 33342 staining-based FACS analysis relative to control2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777549Apparent volume of distribution in BALB/c mouse at 23 mg/kg, iv after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777550Initial plasma concentration in BALB/c mouse at 23 mg/kg, iv after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID516796Antimicrobial activity against amphotericin B-resistant Candida albicans2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Unusual antimalarial meroditerpenes from tropical red macroalgae.
AID777524Metabolic stability in human liver microsomes assessed as formation of metabolite M4 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID1890669Antiviral activity against SARS-CoV-2 isolate USA-WA1/2020 infected in Calu-3 cells at 10 uM preincubated for 24 hrs followed by viral infection and measured after 48 hrs by Hoechst 33342 staining based microscopic method2022Journal of natural products, 03-25, Volume: 85, Issue:3
Marine Natural Products as Leads against SARS-CoV-2 Infection.
AID516794Antimicrobial activity against vancomycin-resistant Enterococcus faecium2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Unusual antimalarial meroditerpenes from tropical red macroalgae.
AID777544Drug degradation in mouse serum at 150 uM after 48 hrs by HPLC analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID516790Antimalarial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Unusual antimalarial meroditerpenes from tropical red macroalgae.
AID777521Metabolic stability in human liver S9 fraction assessed as formation of metabolite M3 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777548Plasma clearance in BALB/c mouse at 23 mg/kg, iv after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777555Half life in BALB/c mouse at 23 mg/kg, iv after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID1890674Antiviral activity against SARS-CoV-2 isolate USA-WA1/2020 infected in human Primary bronchial epithelial cells assessed as reduction in viral RNA replication at 10 uM preincubated for 1 hr followed by viral infection and measured after 48 hrs by qRT-PCR 2022Journal of natural products, 03-25, Volume: 85, Issue:3
Marine Natural Products as Leads against SARS-CoV-2 Infection.
AID777529Half life in human liver microsomes at 10 uM after 24 hrs by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777566Antimalarial activity against Plasmodium yoelii infected in Swiss Webster mouse assessed as decrease in parasite load at 10 mg/kg, ip qd administered on day 2 to 5 by Hoechst 33342 staining-based FACS analysis relative to control2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777568Toxicity in Swiss Webster mouse at 5 to 10 mg/kg, ip qd administered on day 2 to 52013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777562Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 infected in erythrocytes assessed as parasite growth inhibition after 72 hrs by SYBR green I staining-based fluorescence assay2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777535Intrinsic clearance in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID1890672Cytotoxicity against human Calu-3 cells assessed as reduction in cell viability2022Journal of natural products, 03-25, Volume: 85, Issue:3
Marine Natural Products as Leads against SARS-CoV-2 Infection.
AID777554Cmax in BALB/c mouse at 23 mg/kg, ip after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777539Metabolic stability in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis in absence of S9 enzyme and NADPH2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777541Metabolic stability in human liver cytosolic subcellular fraction at 10 uM after 4 hrs by LC-MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777526Metabolic stability in human liver microsomes assessed as formation of metabolite M2 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777523Metabolic stability in human liver S9 fraction assessed as formation of metabolite M1 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777533Drug metabolism in human liver microsomes at 10 uM after 24 hrs by LC-MS analysis in absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777525Metabolic stability in human liver microsomes assessed as formation of metabolite M3 at 10 uM by LC-MS analysis in presence of NADPH and absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777528Intrinsic clearance in human liver microsomes at 10 uM after 24 hrs by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777531Half life in human liver microsomes at 10 uM after 24 hrs by LC-MS analysis in absence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777534Half life in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis in presence of UDPGA2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777556Drug absorption rate constant in BALB/c mouse at 23 mg/kg, ip after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777553Tmax in BALB/c mouse at 23 mg/kg, ip after 1 to 24 hrs by LC-MS/MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID777538Apparent intrinsic clearance in human liver S9 fraction at 10 uM after 24 hrs by LC-MS analysis2013ACS medicinal chemistry letters, Oct-10, Volume: 4, Issue:10
Pharmacokinetics, metabolism, and
AID516795Antimicrobial activity against vancomycin-resistant Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Unusual antimalarial meroditerpenes from tropical red macroalgae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (20.00)29.6817
2010's6 (60.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.38

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 Index12.38 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.38)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0810aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
peloruside a
peloruside A: Antibiotics, Antineoplastic from the sponge Mycale; structure in first source. peloruside A : A macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge, Mycale hentscheli.		2.1710
nitd 609
NITD 609: an antimalarial and coccidiostat; structure in first source		2.0810
heme
Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.		7.0610
s 8932
[no description available]		2.4110aromatic amine;
C-nucleoside;
carboxylic ester;
nitrile;
phosphoramidate ester;
pyrrolotriazine		anticoronaviral agent;
antiviral drug;
prodrug
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0510
Plasmodium falciparum Malaria
[description not available]		02.0610
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.0610