Compounds > cacospongionolide b
Page last updated: 2024-11-12

cacospongionolide b

Description

cacospongionolide B: isolated from the sponge Fasciospongia cavernosa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10386285
CHEMBL ID111739
MeSH IDM0258438

Synonyms (4)

Synonym
cacospongionolide b
CHEMBL111739
bdbm50377908
3-[5-[2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]ethyl]-3,6-dihydro-2h-pyran-2-yl]-2-hydroxy-2h-furan-5-one

Research Excerpts

Overview

Cacospongionolide B is a novel marine metabolite isolated from the sponge Fasciospongia cavernosa.

ExcerptReferenceRelevance
"1. Cacospongionolide B is a novel marine metabolite isolated from the sponge Fasciospongia cavernosa. "( Modulation of acute and chronic inflammatory processes by cacospongionolide B, a novel inhibitor of human synovial phospholipase A2.
Alcaraz, MJ; De Giulio, A; De Rosa, S; García Pastor, P; Payá, M, 1999)		1.17
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Phospholipase A2Apis mellifera (honey bee)IC50 (µMol)35.40000.07003.85707.5000AID401446
Phospholipase A2, membrane associatedRattus norvegicus (Norway rat)IC50 (µMol)36.90000.12000.12000.1200AID401444
Phospholipase A2, membrane associatedHomo sapiens (human)IC50 (µMol)45.50000.00301.08118.0000AID401442; AID401443
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
phospholipid metabolic processPhospholipase A2, membrane associatedHomo sapiens (human)
inflammatory responsePhospholipase A2, membrane associatedHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPhospholipase A2, membrane associatedHomo sapiens (human)
lipid catabolic processPhospholipase A2, membrane associatedHomo sapiens (human)
killing of cells of another organismPhospholipase A2, membrane associatedHomo sapiens (human)
low-density lipoprotein particle remodelingPhospholipase A2, membrane associatedHomo sapiens (human)
intestinal stem cell homeostasisPhospholipase A2, membrane associatedHomo sapiens (human)
phosphatidylethanolamine metabolic processPhospholipase A2, membrane associatedHomo sapiens (human)
phosphatidylcholine metabolic processPhospholipase A2, membrane associatedHomo sapiens (human)
phosphatidic acid metabolic processPhospholipase A2, membrane associatedHomo sapiens (human)
arachidonic acid secretionPhospholipase A2, membrane associatedHomo sapiens (human)
positive regulation of inflammatory responsePhospholipase A2, membrane associatedHomo sapiens (human)
defense response to Gram-positive bacteriumPhospholipase A2, membrane associatedHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadePhospholipase A2, membrane associatedHomo sapiens (human)
regulation of neutrophil activationPhospholipase A2, membrane associatedHomo sapiens (human)
negative regulation of T cell proliferationPhospholipase A2, membrane associatedHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
phospholipase A2 activityPhospholipase A2, membrane associatedHomo sapiens (human)
phospholipid bindingPhospholipase A2, membrane associatedHomo sapiens (human)
calcium-dependent phospholipase A2 activityPhospholipase A2, membrane associatedHomo sapiens (human)
calcium ion bindingPhospholipase A2, membrane associatedHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
extracellular regionPhospholipase A2, membrane associatedHomo sapiens (human)
extracellular spacePhospholipase A2, membrane associatedHomo sapiens (human)
mitochondrial outer membranePhospholipase A2, membrane associatedHomo sapiens (human)
endoplasmic reticulumPhospholipase A2, membrane associatedHomo sapiens (human)
endoplasmic reticulum membranePhospholipase A2, membrane associatedHomo sapiens (human)
plasma membranePhospholipase A2, membrane associatedHomo sapiens (human)
secretory granulePhospholipase A2, membrane associatedHomo sapiens (human)
perinuclear region of cytoplasmPhospholipase A2, membrane associatedHomo sapiens (human)
extracellular exosomePhospholipase A2, membrane associatedHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID360513Antimicrobial activity against Bacillus subtilis DSM 3471995Journal of natural products, Nov, Volume: 58, Issue:11
Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa.
AID158778Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated with Tris buffer for 5 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID158772Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated for 5 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID401444Inhibition of rat air pouch group2 sPLA2 at 10 uM by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID401443Inhibition of human synovial group2 sPLA2 by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID401442Inhibition of human synovial group2 sPLA2 at 10 uM by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID158771Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated for 15 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID401448Cytotoxicity against human neutrophils by MTT assay1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID401439Inhibition of Naja naja venom group1 sPLA2 at 10 uM by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID158776Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated with Hydroxylamine for 60 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID158773Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated for 60 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID401446Inhibition of bee venom group3 sPLA2 at 10 uM by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID360512Toxicity against Artemia salina1995Journal of natural products, Nov, Volume: 58, Issue:11
Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa.
AID158775Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated with Hydroxylamine for 5 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID158774Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated with Hydroxylamine for 15 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID158777Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated with Tris buffer for 15 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID401447Inhibition of bee venom group3 sPLA2 by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID401441Inhibition of pig pancreatic group1 sPLA2 by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID158779Inhibitory activity against bee secretory Phospholipase A2 enzyme when pre-incubated with Tris buffer for 60 minutes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.
AID401445Inhibition of rat air pouch group2 sPLA2 by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID401440Inhibition of pig pancreatic group1 sPLA2 at 10 uM by liquid scintillation counting1998Journal of natural products, Jul, Volume: 61, Issue:7
A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.
AID360514Antimicrobial activity against Micrococcus luteus DSM 3481995Journal of natural products, Nov, Volume: 58, Issue:11
Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa.
[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's5 (50.00)18.2507
2000's4 (40.00)29.6817
2010's1 (10.00)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: 11.86

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 Index11.86 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.86)

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
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		1.9910aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		3.6290butan-4-olidemetabolite;
neurotoxin
furaldehyde
Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.		2.0310aldehyde;
furans		Maillard reaction product;
metabolite
manoalide
manoalide: phospholipase A2 inhibitor; sesterterpene from marine sponge L. variabilis; structure given in first source. manoalide : A sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.		7.420butenolide;
lactol;
sesterterpenoid		EC 3.1.1.4 (phospholipase A2) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
metabolite
scalaradial
scalaradial: RN refers to the (5alpha,12alpha,17abeta)-isomer; a marine natural product isolated from the sponge Cacospongia sp.; structure given in first source. scalaradial : A scalarane sesterterpenoid with formula C27H40O4. It is a natural product found in the marine sponges Spongia officinalis and Cacospongia mollior, and exhibits anti-inflammatory activity.		2.0710acetate ester;
carbotetracyclic compound;
dialdehyde;
enal;
scalarane sesterterpenoid		animal metabolite;
anti-inflammatory agent;
apoptosis inducer;
EC 3.1.1.4 (phospholipase A2) inhibitor;
marine metabolite;
TRP channel blocker
ConditionIndicatedRelationship StrengthStudiesTrials
Anasarca
[description not available]		02.420
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.420
Chronic Illness
[description not available]		0210
Adjuvant Arthritis
[description not available]		0210
Innate Inflammatory Response
[description not available]		0210
Acute Disease
Disease having a short and relatively severe course.		0210
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		0210
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		0210
chemdatabank.com