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

vibsanin b

Description

vibsanin B : A vibsane diterpenoid that is (2Z,6E,10E)-cycloundeca-2,6,10-trien-1-one which is substituted at positions 2, 5, 5, 8, 9, and 9 by hydroxymethyl, methyl, 2-methylpent-2-en-5-yl, 3-methylbut-2-enoyloxy, hydroxy, and methyl groups, respectively (the 5S,8R,9R stereoisomer). It has been found to inhibit root growth in rice seedlings (IC50 0.14 mM). [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 CID15817377
CHEMBL ID497443
CHEBI ID131781
MeSH IDM000607246

Synonyms (7)

Synonym
CHEMBL497443
CHEBI:131781
vibsanine b
vibsanin b
(1r,2e,4s,6z,9e,11r)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-en-1-yl)-8-oxocycloundeca-2,6,9-trien-1-yl 3-methylbut-2-enoate
Q27225253
[(1r,2e,4s,6z,9e,11r)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-enyl)-8-oxocycloundeca-2,6,9-trien-1-yl] 3-methylbut-2-enoate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
plant growth retardantnull
[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
vibsane diterpenoidAny deterpenoid whose with a structure that is characteristically found in the Viburnum species.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
cyclic terpene ketoneAn alicyclic ketone in which the carbocyclic ring structure forms part of a terpene skeleton.
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.
[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 (25)

Assay IDTitleYearJournalArticle
AID1471421Antiproliferative activity against human HuH7 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471401Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471415Antiproliferative activity against human A549 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471449Inhibition of firefly luciferase activity using luciferin substrate at 10 uM after 30 mins by luminescence assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471414Antiproliferative activity against human SMMC7721 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID378025Cytotoxicity against human KB cells2006Journal of natural products, Jul, Volume: 69, Issue:7
Neovibsanin F and its congeners, rearranged vibsane-type diterpenes from Viburnum suspensum.
AID1471418Inhibition of HSP90 in rabbit reticulocyte lysate assessed as decrease in HSP90-dependant refolding of firefly luciferase at 10 uM after 30 mins by luciferase gene based assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471443Drug metabolism in deionized water assessed as compound decomposition at 100 degreeC after 10 mins by HPLC analysis relative to control2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471405Antiproliferative activity against human MDA-MB-468 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471420Antiproliferative activity against human AGS cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471447Half life of compound in toluene at 60 degreeC by HPLC analysis2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471425Toxicity in 3 days post fertilized zebrafish embryo assessed as changes in embryonic phenotypes at 4 to 16 uM after 12 hrs2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471422Antiproliferative activity against human HeLa cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471419Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471406Antiproliferative activity against human SKBR3 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471416Antiproliferative activity against human HL60 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471412Inhibition of FITC-geldanamycin binding to human FLAG-tagged HSP90alpha N-terminal domain2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471423Antiproliferative activity against human BT474 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471417Antiproliferative activity against human SW480 cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471442Half life of compound in toluene at 110 degreeC by HPLC analysis2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471448Drug degradation in pH 7.4 PBS at 37 degreeC after 12 hrs by HPLC analysis relative to control2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471413Inhibition of FITC-geldanamycin binding to human FLAG-tagged HSP90beta N-terminal domain2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID378023Toxicity in brine shrimp2006Journal of natural products, Jul, Volume: 69, Issue:7
Neovibsanin F and its congeners, rearranged vibsane-type diterpenes from Viburnum suspensum.
AID1471444Stability of compound in boiling ethyl alcohol by HPLC analysis2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
AID1471424Cytotoxicity against human BEAS2B cells assessed as reduction in cell viability after 48 hrs by MTT assay2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.78

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 Index12.78 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.72 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.78)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
Berberine chloride (TN)
[no description available]		2.0310organic molecular entity
novobiocin
Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.		2.1510carbamate ester;
ether;
hexoside;
hydroxycoumarin;
monocarboxylic acid amide;
monosaccharide derivative;
phenols		antibacterial agent;
antimicrobial agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
Escherichia coli metabolite;
hepatoprotective agent
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatocellular Carcinoma
[description not available]		02.610
Cancer of Liver
[description not available]		02.610
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.610
Liver Neoplasms
Tumors or cancer of the LIVER.		02.610
Allergic Encephalomyelitis
[description not available]		02.1110
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