epolactaene

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

Description

epolactaene: a neuritogenic compound in human neuroblastoma cells; isolated from Penicillium sp. BM1689-P; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	6442272
CHEMBL ID	183869
MeSH ID	M0251105

Synonyms (13)

Synonym
epolactaene
CHEMBL183869
167782-17-4
4s7a4hla92 ,
unii-4s7a4hla92
Q15410943
methyl (2e,3e,5e,9e)-2-ethylidene-11-[(1r,5r)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate
epolactaene, (+)-
(+)-epolactaene
methyl (2e,3e,5e,9e)-2-ethylidene-11-((1r,5r)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo(3.1.0)hex-1-yl)-4,10-dimethyl-11-oxo-3,5,9-undecatrienoate
3,5,9-undecatrienoic acid, 2-ethylidene-11-[(1r,5r)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hex-1-yl]-4,10-dimethyl-11-oxo-, methyl ester, (2e,3e,5e,9e)-
DTXSID301045462
methyl (2e,3e,5e,9e)-2-ethylidene-11-((1r,5r)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl)-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate

Research Excerpts

Overview

Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp.

Excerpt	Reference	Relevance
"Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp. "	( Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity. Hayashi, Y; Kakeya, H; Nagumo, Y; Osada, H; Shoji, M; Uno, T; Yamaguchi, J, 2004)	2.04
"Epolactaene is a microbial metabolite isolated from Penicillium sp., from which we synthesized its derivative ETB (epolactaene tertiary butyl ester). "	( Epolactaene binds human Hsp60 Cys442 resulting in the inhibition of chaperone activity. Dohmae, N; Hayashi, Y; Kakeya, H; Nagumo, Y; Osada, H; Shoji, M, 2005)	3.21

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay ID	Title	Year	Journal	Article
AID382217	cytotoxicity against human BALL1 cells by MTT assay	2008	Bioorganic & medicinal chemistry, May-01, Volume: 16, Issue:9	Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation.
AID244420	Competitive binding to human heat shock protein Hsp60; 60-90%	2004	Bioorganic & medicinal chemistry letters, Sep-06, Volume: 14, Issue:17	Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity.
AID248710	inhibitory concentration against human neuroblastoma SH-SY5Y cells (cell viability was assessed by MTT assay)	2004	Bioorganic & medicinal chemistry letters, Sep-06, Volume: 14, Issue:17	Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity.
AID252840	In vitro Hsp60 chaperone activity in mitochondrial malate dehydrogenase (MDH) refolding assay	2004	Bioorganic & medicinal chemistry letters, Sep-06, Volume: 14, Issue:17	Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity.
AID248667	inhibitory concentration against human T-lymphoma Jurkat cells (cell viability was assessed by MTT assay)	2004	Bioorganic & medicinal chemistry letters, Sep-06, Volume: 14, Issue:17	Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (13.33)	18.2507
2000's	11 (73.33)	29.6817
2010's	1 (6.67)	24.3611
2020's	1 (6.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.33

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 moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	17.33 (24.57)
Research Supply Index	2.77 (2.92)
Research Growth Index	4.92 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (17.33)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (6.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	14 (93.33%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	3.13	1	pyrrole; secondary amine
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.04	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.03	1	titanium group element atom
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.02	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	7.04	1	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
cytotrienin a cytotrienin A: induces apoptosis in leukemia cells; structure in first source. cytotrienin A : A 21-membered macrocyclic lactam which contains three conjugated double bonds as part of the ring system. It acts as an apoptosis inducer in human leukemia HL-60 cells and is isolated from Streptomyces sp.	3.13	1	cyclopropanecarboxylate ester; ether; hydroquinones; lactam; macrocycle; secondary alcohol	antibacterial agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; metabolite
rifamycins [no description available]	3.13	1

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.02	1
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.	2.02	1
B-Cell Leukemia [description not available]	2.42	2
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	2.68	3

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