Page last updated: 2024-11-07

beta-hydroxyisovalerylshikonin

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Description

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

Cross-References

ID SourceID
PubMed CID479502
SCHEMBL ID842120
MeSH IDM0303588
PubMed CID100203
MeSH IDM0303588

Synonyms (26)

Synonym
beta-hivs
3'-hydroxyisovalerylshikonin
[(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate
SCHEMBL842120
nsc 110263
HY-N4201
CS-0032419
(r)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate
MS-26439
-hydroxyisovalerylshikonin
alkannin-.beta.-hydroxyisovalerate
alkannin-beta-hydroxyisovalerate
nsc373954
87798-74-1
nsc-373954
nsc110263
nsc-110263
7415-78-3
beta-hydroxyisovalerylshikonin
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate
inchi=1/c21h24o7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27h,8,10h2,1-4h3
mxanjrghsfelej-uhfffaoysa-
nsc 373954
AKOS037515319
BCP34280
3'-hydroxyisovalerylshikonin; (c)micro-hydroxyisovalerylshikonin
[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)
Sterol O-acyltransferase 2Homo sapiens (human)IC50 (µMol)169.80000.11003.20369.2000AID305640
Sterol O-acyltransferase 1Homo sapiens (human)IC50 (µMol)186.90000.02501.79758.0000AID305641
NeuraminidaseInfluenza A virus (A/Brevig Mission/1/1918(H1N1))IC50 (µMol)40.50000.00340.00340.0034AID644395
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
cholesterol metabolic processSterol O-acyltransferase 2Homo sapiens (human)
macrophage derived foam cell differentiationSterol O-acyltransferase 2Homo sapiens (human)
cholesterol storageSterol O-acyltransferase 2Homo sapiens (human)
intestinal cholesterol absorptionSterol O-acyltransferase 2Homo sapiens (human)
cholesterol effluxSterol O-acyltransferase 2Homo sapiens (human)
very-low-density lipoprotein particle assemblySterol O-acyltransferase 2Homo sapiens (human)
low-density lipoprotein particle clearanceSterol O-acyltransferase 2Homo sapiens (human)
cholesterol homeostasisSterol O-acyltransferase 2Homo sapiens (human)
cholesterol metabolic processSterol O-acyltransferase 1Homo sapiens (human)
cholesterol metabolic processSterol O-acyltransferase 1Homo sapiens (human)
macrophage derived foam cell differentiationSterol O-acyltransferase 1Homo sapiens (human)
cholesterol storageSterol O-acyltransferase 1Homo sapiens (human)
cholesterol effluxSterol O-acyltransferase 1Homo sapiens (human)
very-low-density lipoprotein particle assemblySterol O-acyltransferase 1Homo sapiens (human)
low-density lipoprotein particle clearanceSterol O-acyltransferase 1Homo sapiens (human)
cholesterol homeostasisSterol O-acyltransferase 1Homo sapiens (human)
positive regulation of amyloid precursor protein biosynthetic processSterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
fatty-acyl-CoA bindingSterol O-acyltransferase 2Homo sapiens (human)
sterol O-acyltransferase activitySterol O-acyltransferase 2Homo sapiens (human)
protein bindingSterol O-acyltransferase 2Homo sapiens (human)
cholesterol bindingSterol O-acyltransferase 2Homo sapiens (human)
acyltransferase activitySterol O-acyltransferase 2Homo sapiens (human)
cholesterol O-acyltransferase activitySterol O-acyltransferase 2Homo sapiens (human)
fatty-acyl-CoA bindingSterol O-acyltransferase 1Homo sapiens (human)
sterol O-acyltransferase activitySterol O-acyltransferase 1Homo sapiens (human)
protein bindingSterol O-acyltransferase 1Homo sapiens (human)
cholesterol bindingSterol O-acyltransferase 1Homo sapiens (human)
cholesterol O-acyltransferase activitySterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulumSterol O-acyltransferase 2Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 2Homo sapiens (human)
brush borderSterol O-acyltransferase 2Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 2Homo sapiens (human)
endoplasmic reticulumSterol O-acyltransferase 1Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 1Homo sapiens (human)
membraneSterol O-acyltransferase 1Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID615261Cytotoxicity against human HeLa cells by MTT assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues.
AID644401Inhibition of alpha-glucosidase at 200 uM2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID305640Inhibition of human ACAT2 expressed in Hi5 cells2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.
AID644394Competitive inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catalytic domain using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate by Lineweaver-Burk and Dixon plot analysis2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID669244Cytotoxicity against human HCT116 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID669243Cytotoxicity against human U251 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID669247Cytotoxicity against human WM9 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID644402Inhibition of beta-glucosidase at 200 uM2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID669249Cytotoxicity against human MRC5 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID644395Inhibition of recombinant influenza A virus H1N1 A/Bervig_Mission/1/18 sialidase activity using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate by fluorimetric analysis2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID363329Cytotoxicity against MDR1 Pgp overexpressing human HepG2 cells after 24 hrs by MTT assay2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.
AID669245Cytotoxicity against human SBcl2 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID644397Inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catalytic domain using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate at IC50 concentration pre-incubated for 10 mins prior substrate additio2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID669250Selectivity ratio of IC50 for human MRC5 cells to IC50 for human CCRF-CEM cells2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID644393Inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catalytic domain using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate by fluorimetric analysis2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID669242Cytotoxicity against human MDA-MB-231 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID644398Reversible inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catalytic domain using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate compound pre-incubated prior to substrate addition by fluori2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID669246Cytotoxicity against human WM35 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID669241Cytotoxicity against human CCRF-CEM cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
AID363328Cytotoxicity against MDR1 Pgp under-expressing human HCT116 cells after 24 hrs by MTT assay2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.
AID305641Inhibition of human ACAT1 expressed in Hi5 cells2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.
AID644403Inhibition of rhamnosidase at 200 uM2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID644396Noncompetitive inhibition of recombinant influenza A virus H1N1 A/Bervig_Mission/1/18 sialidase activity using 4-methylumbelliferyl-alpha-D-N-acetylneuraminic acid sodium salt hydrate as substrate by Lineweaver-Burk and Dixon plot analysis2012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
AID615262Cytotoxicity against human DU145 cells by MTT assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues.
AID669248Cytotoxicity against human WM164 cells after 72 hrs by XTT assay2012Journal of natural products, May-25, Volume: 75, Issue:5
Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.00)18.2507
2000's12 (60.00)29.6817
2010's5 (25.00)24.3611
2020's2 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.57

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 Index12.57 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]