Compounds > dihydrochelerythrine
Page last updated: 2024-12-08

dihydrochelerythrine

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

Description

dihydrochelerythrine: trypanocidal and antileishmanial dihydrochelerythrine derivative from Garcinia lucida; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
GarciniagenusA plant genus of the family CLUSIACEAE. Members contain XANTHONES.[MeSH]ClusiaceaeThe mangosteen plant family (sometimes classified as Guttiferae; also known as Hypericaceae) of the order THEALES, subclass Dilleniidae, class Magnoliopsida. It includes trees and shrubs with resinous, sticky sap, usually with broad-ended, oblong, leathery leaves with a strong, central vein, flowers with many stamens.[MeSH]

Cross-References

ID SourceID
PubMed CID485077
CHEMBL ID400359
CHEBI ID140672
SCHEMBL ID3864468
MeSH IDM0516518

Synonyms (20)

Synonym
6880-91-7
1,2-dimethoxy-12-methyl-13h-[1,3]benzodioxolo[5,6-c]phenanthridine
12,13-dihydrochelerythrine
(1,3)benzodioxolo(5,6-c)phenanthridine, 12,13-dihydro-1,2-dimethoxy-12-methyl-
dihydrochelerythrine
CHEBI:140672
CHEMBL400359
1,2-dimethoxy-12-methyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
3AS1
3ARW
SCHEMBL3864468
CS-3820
DTXSID70218913
AC-34694
HY-N0903
AKOS032948894
mfcd02183360
BCP33364
FT-0775799
AS-77280

Research Excerpts

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

Drug Classes (1)

ClassDescription
benzophenanthridine alkaloidA specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.
[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]

Pathways (1)

PathwayProteinsCompounds
chelerythrine biosynthesis1024
chelerythrine biosynthesis823

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1377260Cytotoxicity against human MCF7 cells assessed as cell growth inhibition at 50 uM after 48 hrs by SRB assay relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Mild C(sp
AID311526Antitrypanosomal activity against Trypanosoma brucei brucei MITat 1.2 variant 2212007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID1377259Cytotoxicity against human HCT15 cells assessed as cell growth inhibition at 50 uM after 48 hrs by SRB assay relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Mild C(sp
AID1304392Antiproliferative activity against human A549 cells at 0.1 to 20 uM after 72 hrs by MTT assay2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID311529Antileishmanial activity against Leishmania donovani promastigotes at 10 uM2007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID1304391Antiproliferative activity against human HeLa cells at 0.1 to 20 uM after 72 hrs by MTT assay2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1072520Antiviral activity against Hepatitis B virus assessed as inhibition of Hepatitis B virus surface antigen secretion2014European journal of medicinal chemistry, Mar-21, Volume: 75A review of non-nucleoside anti-hepatitis B virus agents.
AID311530Antileishmanial activity against Leishmania donovani promastigotes at 1 uM2007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID1304386Binding affinity to duplex DNA (unknown origin) assessed as change in melting temperature at 50 uM by circular dichroism spectroscopic analysis2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1304380Binding affinity to c-myc G-quadruplex DNA (unknown origin) incubated for 30 mins by Taq DNA polymerase stop assay2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1236962Antiproliferative activity against human HCT116 cells assessed as inhibition of cell viability after 48 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Jul-15, Volume: 25, Issue:14
Antiproliferative activity of O4-benzo[c]phenanthridine alkaloids against HCT-116 and HL-60 tumor cells.
AID1072518Antiviral activity against Hepatitis B virus assessed as inhibition of Hepatitis B virus e antigen secretion2014European journal of medicinal chemistry, Mar-21, Volume: 75A review of non-nucleoside anti-hepatitis B virus agents.
AID1304397Antiproliferative activity against human A431 cells assessed as reduction in cell viability at 20 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1304388Binding affinity to c-myc DNA mutant (unknown origin) up to 80 uM incubated for 30 mins by Taq DNA polymerase stop assay2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1304393Antiproliferative activity against human PC3 cells at 0.1 to 20 uM after 72 hrs by MTT assay2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID311532Cytotoxicity against african green monkey Vero cells2007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID311527Antileishmanial activity against Leishmania donovani axenic amastigotes2007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID1236963Antiproliferative activity against human HL60 cells assessed as inhibition of cell viability after 48 hrs by WST-1 assay2015Bioorganic & medicinal chemistry letters, Jul-15, Volume: 25, Issue:14
Antiproliferative activity of O4-benzo[c]phenanthridine alkaloids against HCT-116 and HL-60 tumor cells.
AID1377258Cytotoxicity against human PC3 cells assessed as cell growth inhibition at 50 uM after 48 hrs by SRB assay relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Mild C(sp
AID1304381Binding affinity to c-myc G-quadruplex DNA (unknown origin) assessed as stabilization of preformed parallel topology up to 5 molar equivalents by circular dichroism spectroscopic analysis in absence of metal ion2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1377252Cytotoxicity against human HGF cells assessed as cell growth inhibition at 50 uM after 48 hrs by SRB assay relative to control2017European journal of medicinal chemistry, Sep-29, Volume: 138Mild C(sp
AID1304379Binding affinity to c-myc G-quadruplex DNA (unknown origin) by UV-visible absorption spectroscopic analysis2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID311528Antileishmanial activity against Leishmania donovani promastigotes at 100 uM2007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID1304385Binding affinity to c-Kit1 G-quadruplex DNA (unknown origin) assessed as change in melting temperature at 50 uM by circular dichroism spectroscopic analysis2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1304389Antiproliferative activity against human HCT116 cells assessed as reduction in cell viability at 20 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID311531Antileishmanial activity against Leishmania donovani promastigotes in RAW cells assessed as reduction in infection2007Journal of natural products, Oct, Volume: 70, Issue:10
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida.
AID1304384Binding affinity to c-myc G-quadruplex DNA (unknown origin) assessed as change in melting temperature at 50 uM by circular dichroism spectroscopic analysis2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1304382Binding affinity to c-Kit1 G-quadruplex DNA (unknown origin) assessed as stabilization of preformed parallel topology up to 5 molar equivalents by circular dichroism spectroscopic analysis in absence of metal ion2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID1304395Antiproliferative activity against human MDA-MB-231 cells assessed as reduction in cell viability at 20 uM after 72 hrs by MTT assay relative to control2016Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13
Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2011The Journal of biological chemistry, Jul-08, Volume: 286, Issue:27
Potent family-18 chitinase inhibitors: x-ray structures, affinities, and binding mechanisms.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2011The Journal of biological chemistry, Jul-08, Volume: 286, Issue:27
Potent family-18 chitinase inhibitors: x-ray structures, affinities, and binding mechanisms.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (18.75)29.6817
2010's12 (75.00)24.3611
2020's1 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.29

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 Index12.29 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chelerythrine
chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.		3.1850benzophenanthridine alkaloid;
organic cation		antibacterial agent;
antineoplastic agent;
EC 2.7.11.13 (protein kinase C) inhibitor
pentamidine
Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.		2.0310aromatic ether;
carboxamidine;
diether		anti-inflammatory agent;
antifungal agent;
calmodulin antagonist;
chemokine receptor 5 antagonist;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
NMDA receptor antagonist;
S100 calcium-binding protein B inhibitor;
trypanocidal drug;
xenobiotic
pentoxifylline
[no description available]		2.0610oxopurine
propentofylline
[no description available]		2.0610oxopurine
sanguinarine
benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.		2.0510alkaloid antibiotic;
benzophenanthridine alkaloid;
botanical anti-fungal agent
suramin
Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.		2.0310naphthalenesulfonic acid;
phenylureas;
secondary carboxamide		angiogenesis inhibitor;
antinematodal drug;
antineoplastic agent;
apoptosis inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
GABA antagonist;
GABA-gated chloride channel antagonist;
purinergic receptor P2 antagonist;
ryanodine receptor agonist;
trypanocidal drug
protocatechualdehyde
protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure		3.1910dihydroxybenzaldehyde
aloe emodin
aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.		3.1910aromatic primary alcohol;
dihydroxyanthraquinone		antineoplastic agent;
plant metabolite
chrysophanic acid
chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.		3.1910dihydroxyanthraquinoneanti-inflammatory agent;
antiviral agent;
plant metabolite
physcione
physcione: structure. physcion : A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources.		3.1910dihydroxyanthraquinoneanti-inflammatory agent;
antibacterial agent;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
hepatoprotective agent;
metabolite
nitidine chloride
[no description available]		2.1110
nitazoxanide
nitazoxanide: a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug		3.1910benzamides;
carboxylic ester
lamivudine
[no description available]		3.1910monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
sesamin
(+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.		2.0310benzodioxoles;
furofuran;
lignan		antineoplastic agent;
neuroprotective agent;
plant metabolite
chelerythrine chloride
[no description available]		2.1110
dihydronitidine
dihydronitidine: molecular structure given in first source		2.1110
dihydrosanguinarine
[no description available]		3.3360benzophenanthridine alkaloidantifungal agent;
metabolite
helioxanthin
helioxanthin: structure in first source. 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.		3.1910benzodioxoles;
furonaphthodioxole;
lignan		anti-HBV agent;
antineoplastic agent;
plant metabolite
6-acetonyldihydrochelerythrine
6-acetonyldihydrochelerythrine: from formosan Argemone mexicana; structure in first source		2.0310
chrysophanol 8-o-glucoside
chrysophanol 8-O-glucoside: has anti-hepatitis B virus activity; also has antiplatelet and anticoagulant activities; isolated from Rheum palmatum. chrysophanol 8-O-beta-D-glucoside : A beta-D-glucoside in which the aglycone species is chrysophanol, the glycosidic linkage being to the hydroxy group at C-8.		3.1910beta-D-glucoside;
monohydroxyanthraquinone
bay 41-4109
BAY 41-4109: structure in first source		3.1910
hbf 0259
[no description available]		3.1910
wogonin
wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.		3.1910dihydroxyflavone;
monomethoxyflavone		angiogenesis inhibitor;
antineoplastic agent;
cyclooxygenase 2 inhibitor;
plant metabolite
fagaramide
[no description available]		2.0310cinnamamides;
secondary carboxamide
helioxanthin 8-1
helioxanthin 8-1: an antiviral agent; structure in first source		3.1910
artesunate
artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether		3.1910artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer
leucamide a
leucamide A: a cytotoxic heptapeptide from the Australian sponge Leucetta microraphis; structure in first source		3.1910
astragaloside IV
[no description available]		3.1910pentacyclic triterpenoid;
triterpenoid saponin		anti-inflammatory agent;
antioxidant;
EC 4.2.1.1 (carbonic anhydrase) inhibitor;
neuroprotective agent;
plant metabolite;
pro-angiogenic agent
8-hydroxydihydrosanguinarine
8-hydroxydihydrosanguinarine: compound with potent acetylcholinesterase inhibitory activity from Chelidonium majus L.; structure in first source		2.0510
rosamultin
rosamultin: isolated from roots of Rosa multiflora; RN not in Chemline 3/87; RN from Chem Abstracts Index Guide 1985		3.1910
2-hydroxybenzoyl-n-(5-chlorothiazol-2-yl)amide
2-hydroxybenzoyl-N-(5-chlorothiazol-2-yl)amide: an antiviral agent effective against hepatitis B virus; structure in first source		3.1910
alisol f
[no description available]		3.1910
alisol a 24-acetate
alisol A 24-acetate: isolated from Alismatis Rhizoma; structure in first source		3.1910
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatitis B Virus Infection
[description not available]		03.0110
Hepatitis B
INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.		03.0110
Genome Instability
[description not available]		02.1310
Astrocytoma, Grade IV
[description not available]		02.1710
Experimental Neoplasms
[description not available]		02.1710
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		07.1710
Ciliophora Infections
Infections with protozoa of the phylum CILIOPHORA.		02.0610
Fish Diseases
Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).		02.0610
Acute Promyelocytic Leukemia
[description not available]		02.0410
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		02.0410