Page last updated: 2024-12-08

helioxanthin

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

Description

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

helioxanthin : A furonaphthodioxole that is furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9H)-one substituted by a 1,3-benzodioxol-5-yl group at posiiton 10. It is a inhibitor of HBV, HCV and HSV-1 viruses. [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 CID177023
CHEMBL ID436474
CHEBI ID191856
SCHEMBL ID2960321
MeSH IDM0492347

Synonyms (25)

Synonym
7,8-methylenedioxy-1-(3',4'-methylenedioxyphenyl)-2-hydroxymethylnaphthalene-3-carboxylic acid lactone
helioxanthin
zhu-ix-139-1
CHEMBL436474
10-(1,3-benzodioxol-5-yl)-9h-[2]benzofuro[6,5-g][1,3]benzodioxol-7-one
18920-47-3
he-145
CHEBI:191856
10-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9h)-one
10-(2h-1,3-benzodioxol-5-yl)-2h-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9h)-one
JUBRYHUFFFYTGR-UHFFFAOYSA-N
10-benzo[1,3]dioxol-5-yl-9h-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7-one
HY-16678
CS-3196
SCHEMBL2960321
AC-35296
DTXSID90172321
J-690253
ach126447;helioxanthin
EX-A772
10-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d]-1,3-dioxol-7(9h)-one
FT-0700249
ach126447
10-(benzo[d][1,3]dioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9h)-one
furo[3',4':6,7]naphtho[1,2-d]-1,3-dioxol-7(9h)-one, 10-(1,3-benzodioxol-5-yl)-

Research Excerpts

Overview

Helioxanthin is a natural product that inhibits the replication of a number of viruses.

ExcerptReferenceRelevance
"Helioxanthin is a natural product that inhibits the replication of a number of viruses. "( Unique antiviral mechanism discovered in anti-hepatitis B virus research with a natural product analogue.
Cheng, YC; Leung, CH; Li, Y; Robek, MD; Ying, C, 2007
)
1.78

Effects

ExcerptReferenceRelevance
"Helioxanthin and analogues have been demonstrated to suppress gene expression of human hepatitis B virus. "( Synthesis and biological evaluation of helioxanthin analogues.
Chen, TA; Hsieh, JY; Janmanchi, D; Jhuang, HJ; Lin, CH; Tseng, YP; Yeh, SF, 2013
)
2.1
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
anti-HBV agentAn antiviral agent that destroys or inhibits the replication of the hepatitis B virus.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[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 (3)

ClassDescription
benzodioxoles
furonaphthodioxole
lignanAny phenylpropanoid derived from phenylalanine via dimerization of substituted cinnamic alcohols, known as monolignols, to a dibenzylbutane skeleton. Note that while individual members of the class have names ending ...lignane, ...lignene, ...lignadiene, etc., the class names lignan, neolignan, etc., do not end with an "e".
[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 (36)

Assay IDTitleYearJournalArticle
AID1175582Increase in transendothelial electrical resistance in RBEC at 5 uM after 2 hrs relative to control2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID246342Effective concentration to inhibit 50% of epstein Barr virus replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID1175568Cytotoxicity against human A2058 cells at 1 to 10 uM after 8 hrs by EZ4U assay2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID401841Insecticidal activity against yellow fever mosquito larvae1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID401838Toxicity in Artemia salina1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID1175583Increase in integrity of human CMEC/D3 cells at 2 uM after 2 hrs by ZO-1 staining method2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID1175581Increase in integrity of RBEC at 5 uM after 2 hrs by ZO-1 staining method2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID246413Effective concentration to inhibit 50% of herpes simplex virus type 2 replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID1175569Cytotoxicity against human CMEC/D3 cells at 1 to 10 uM after 8 hrs by EZ4U assay2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID1175573Inhibition of migration of human A2058 cells assessed as filopodia at 5 uM using Alexa-488-labeled phalloidin by microscopy2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID246412Effective concentration to inhibit 50% of herpes simplex virus type 1 replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID249056Cytotoxicity against CEM cell lines of human2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID246416Effective concentration to inhibit 50% of human immunodeficiency virus replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID1444844Cytotoxicity against human HepG2(2.2.15) cells assessed as reduction in cell viability after 3 days by methylene blue assay2017Journal of medicinal chemistry, 08-10, Volume: 60, Issue:15
Past, Current, and Future Developments of Therapeutic Agents for Treatment of Chronic Hepatitis B Virus Infection.
AID1175578Inhibition of adhesion of human A2058 cells to endothelial cells at 10 uM pretreated for 3 hrs before adhesion and during adhesion2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID1444845Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA level after 6 days by Southern blot analysis2017Journal of medicinal chemistry, 08-10, Volume: 60, Issue:15
Past, Current, and Future Developments of Therapeutic Agents for Treatment of Chronic Hepatitis B Virus Infection.
AID1175584Inhibition of migration of human CMEC/D3 cells after 24 hrs by wound-healing assay2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID1175580Inhibition of adhesion of human A2058 cells to endothelial cells at 2 uM pretreated to endothelial cells for 3 hrs before adhesion2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID249057Cytotoxicity against MT-2 cell lines of human2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID743634Antiviral activity against Hepatitis B virus infected in human 1.3ES2 cells assessed as inhibition of viral core promoter activity at 3 uM after 24 hrs by luciferase reporter gene assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Synthesis and biological evaluation of helioxanthin analogues.
AID1175577Inhibition of adhesion of human A2058 cells to endothelial cells at 2 uM pretreated for 3 hrs before adhesion and during adhesion2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID246329Effective concentration to inhibit 50% of hepatitis C virus replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID1072531Antiviral activity against Hepatitis B virus2014European journal of medicinal chemistry, Mar-21, Volume: 75A review of non-nucleoside anti-hepatitis B virus agents.
AID246328Effective concentration to inhibit 50% of hepatitis B virus replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID1175579Inhibition of adhesion of human A2058 cells to endothelial cells at 5 uM pretreated for 3 hrs before adhesion2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID458521Antiviral activity against Hepatitis B virus in human HepA2 cells assessed as reduction of HBsAg secretion after 48 hrs by enzyme immunoassay2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents.
AID1175572Inhibition of migration of human A2058 cells assessed as elongated shape with actin-rich protrusion at 5 uM using Alexa-488-labeled phalloidin by microscopy2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID251782Percent inhibition against Hepatitis C virus replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID1175570Cytotoxicity against RBEC at 1 to 10 uM after 8 hrs by EZ4U assay2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID1175571Inhibition of migration of human A2058 cells assessed as elongated shape and longer protrusion at 5 uM by phase contrast microscopy2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID743641Cytotoxicity against human HepA2 cells after 2 days by MTT assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Synthesis and biological evaluation of helioxanthin analogues.
AID246364Effective concentration to inhibit 50% of cytomegalovirus (CMV) replication in a cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral activity of helioxanthin analogues.
AID743640Antiviral activity against Hepatitis B virus infected in human HepA2 cells assessed as inhibition of viral surface antigen production after 2 days by enzyme immunoassay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Synthesis and biological evaluation of helioxanthin analogues.
AID1175574Inhibition of migration of human A2058 cells assessed as cells with stress fibers at 5 uM using Alexa-488-labeled phalloidin by microscopy2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
AID458522Cytotoxicity against human HepA2 cells after 48 hrs by MTT assay2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents.
AID1175585Inhibition of migration of human CMEC/D3 cells at 10 uM after 24 hrs by wound-healing assay2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (4.17)18.2507
2000's7 (29.17)29.6817
2010's14 (58.33)24.3611
2020's2 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.56

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.

MetricThis Compound (vs All)
Research Demand Index17.56 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index5.60 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]