Compounds > dihydrosanguinarine
Page last updated: 2024-12-07

dihydrosanguinarine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators
FloraRankFlora DefinitionFamilyFamily Definition
CorydalisgenusA plant genus of the family FUMARIACEAE (classified by some in PAPAVERACEAE) that contains isoquinoline alkaloids.[MeSH]PapaveraceaeThe poppy plant family of the order Papaverales, subclass Magnoliidae, class Magnoliopsida. These have bisexual, regular, cup-shaped flowers with one superior pistil and many stamens; 2 or 3 conspicuous, separate sepals and a number of separate petals. The fruit is a capsule. Leaves are usually deeply cut or divided into leaflets.[MeSH]

Cross-References

ID SourceID
PubMed CID124069
CHEMBL ID465678
CHEBI ID17209
SCHEMBL ID420383
MeSH IDM0486703

Synonyms (34)

Synonym
CHEBI:17209 ,
13-methyl-13,14-dihydro-2h,10h-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
dihydroavicine
dihydrosanguinarine ,
3606-45-9
13,14-dihydro-13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine
C05191
13, 14-dihydro-13-methyl-[1, 3]benzodioxolo[5, 6-c]-1, 3-dioxolo[4, 5-i]phenanthridine
bdbm50286637
CHEMBL465678
FT-0667147
(1,3)benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridine, 13,14-dihydro-13-methyl-
dihydro-sanguinarine
3h1zkg80f7 ,
unii-3h1zkg80f7
hydrosanguinarine
dihydro sanguinarine
13,14-dihydrosanguinarine
3AS0
3ARV
SCHEMBL420383
3LLE
CS-3819
HY-N0902
DTXSID00189627
AKOS030526138
AC-34693
Q347588
F17675
24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
MS-25022
24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10.0^{4,8.0^{14,22.0^{17,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
13,14-dihydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin
A937419

Research Excerpts

Effects

ExcerptReferenceRelevance
"Dihydrosanguinarine (DHSG) has recently been identified as a SG metabolite in rat."( The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study.
Anzenbacher, P; Dvorak, Z; Klejdus, B; Kosina, P; Lichnovsky, V; Simanek, V; Stejskal, D; Svobodova, A; Ulrichova, J; Vecera, R; Vicar, J; Vostalova, J; Vrublova, E; Zdarilova, A, 2008)		1.34

Toxicity

ExcerptReferenceRelevance
" These data illustrated that NQO1 involved in the imine bond reduction of sanguinarine and this was a less toxic metabolizing pathway than CYP1A1-metabolizing pathway."( NQO1 involves in the imine bond reduction of sanguinarine and recombinant adeno-associated virus mediated NQO1 overexpression decreases sanguinarine-induced cytotoxicity in rat BRL cells.
Li, YJ; Liu, ZY; Sun, ZL; Zhang, DS, 2014)		0.4

Dosage Studied

ExcerptRelevanceReference
" Thus, repeated dosing of DHSG for 90 days at up to 500 ppm in the diet (i."( The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study.
Anzenbacher, P; Dvorak, Z; Klejdus, B; Kosina, P; Lichnovsky, V; Simanek, V; Stejskal, D; Svobodova, A; Ulrichova, J; Vecera, R; Vicar, J; Vostalova, J; Vrublova, E; Zdarilova, A, 2008)		0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
[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 (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
sanguinarine and macarpine biosynthesis639
sanguinarine and macarpine biosynthesis839

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)100.00000.00000.933210.0000AID1350115
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Protein S100-BBos taurus (cattle)Kd10.700010.700010.700010.7000AID977611
Chain B, Protein S100-BBos taurus (cattle)Kd10.700010.700010.700010.7000AID977611
Chain A, Protein S100-BBos taurus (cattle)Kd10.700010.700010.700010.7000AID977611
Chain A, Protein S100-BBos taurus (cattle)Kd10.700010.700010.700010.7000AID977611
Chain B, Protein S100-BBos taurus (cattle)Kd10.700010.700010.700010.7000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
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
AID1694962Antiproliferative activity against human H1975 cells assessed as inhibition of cell growth incubated for 72 hrs by MTT assay2020RSC medicinal chemistry, Feb-01, Volume: 11, Issue:2
The synthesis and biological evaluation of sanguinarine derivatives as anti-non-small cell lung cancer agents.
AID1694961Antiproliferative activity against human A549 cells assessed as inhibition of cell growth incubated for 72 hrs by MTT assay2020RSC medicinal chemistry, Feb-01, Volume: 11, Issue:2
The synthesis and biological evaluation of sanguinarine derivatives as anti-non-small cell lung cancer agents.
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
AID1152199Inhibition of recombinant human DOPA decarboxylase assessed as inhibition of dopamine production after 30 mins by HPLC method2014Bioorganic & medicinal chemistry letters, Jun-15, Volume: 24, Issue:12
Synthesis of 5-methyl phenanthridium derivatives: a new class of human DOPA decarboxylase inhibitors.
AID1350115Inhibition of human erythrocyte AChE using S-acetylthiocholine iodide as substrate pretreated for 20 mins followed by substrate addition measured after 30 mins by Ellman's method2018Journal of natural products, 02-23, Volume: 81, Issue:2
Mucroniferanines A-G, Isoquinoline Alkaloids from Corydalis mucronifera.
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
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
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.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2010International journal of high throughput screening, Jul-07, Volume: 2010, Issue:1
In vitro screening and structural characterization of inhibitors of the S100B-p53 interaction.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.57)18.7374
1990's0 (0.00)18.2507
2000's8 (28.57)29.6817
2010's17 (60.71)24.3611
2020's2 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.78

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

MetricThis Compound (vs All)
Research Demand Index18.78 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.78)

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%
Other28 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
berberine
[no description available]		2.5420alkaloid antibiotic;
berberine alkaloid;
botanical anti-fungal agent;
organic heteropentacyclic compound		antilipemic drug;
antineoplastic agent;
antioxidant;
EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor;
EC 1.21.3.3 (reticuline oxidase) inhibitor;
EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.11.10 (IkappaB kinase) inhibitor;
EC 3.1.1.4 (phospholipase A2) inhibitor;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor;
EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
hypoglycemic agent;
metabolite;
potassium channel blocker
chelerythrine
chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.		2.7930benzophenanthridine alkaloid;
organic cation		antibacterial agent;
antineoplastic agent;
EC 2.7.11.13 (protein kinase C) inhibitor
nitidine
nitidine: RN given refers to parent cpd; synonym NSC 146397 refers to chloride; structure		2.110phenanthridines
pentoxifylline
[no description available]		2.0610oxopurine
propentofylline
[no description available]		2.0610oxopurine
protopine
[no description available]		2.4720dibenzazecine alkaloidplant metabolite
sanguinarine
benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.		3.72100alkaloid antibiotic;
benzophenanthridine alkaloid;
botanical anti-fungal agent
(+-)stylopine
[no description available]		2.5120
benz(c)acridine
[no description available]		2.0310organonitrogen heterocyclic compound;
polycyclic heteroarene
acridines
Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.		2.0310acridines;
mancude organic heterotricyclic parent;
polycyclic heteroarene		genotoxin
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.1710benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
tetrahydropapaveroline
Tetrahydropapaveroline: A leukomaine (animal alkaloid) formed in brain and liver from dopamine and L-dopa; it may be implicated in psychiatric problems.		2.5220benzylisoquinoline alkaloid;
benzyltetrahydroisoquinoline;
isoquinolinol		human metabolite
dehydrocorydalin
dehydrocorydalin: alkaloid from Corydalis bulbuso D.C. used in therapy of peptic ulcer; RN given refers to parent cpd		2.0310alkaloid
sanguinarine chloride
[no description available]		2.5520
coptisine
coptisine: RN given refers to parent cpd		2.2110alkaloidmetabolite
homochelidonine
homochelidonine: structure in first source		2.0810benzophenanthridine alkaloid
chelidonine
chelidonine: benzophenanthridine derived from scoulerine from Chelidonium majus; RN given refers to parent cpd (chelidonine, (5bR-(5balpha,6beta,12alpha))-isomer)		2.0810alkaloid antibiotic;
alkaloid fundamental parent;
benzophenanthridine alkaloid
tetrahydrocolumbamine
tetrahydrocolumbamine: a dopamine receptor ligand; from Polygala tenuifolia; structure given in first source. (S)-tetrahydrocolumbamine : A berberine alkaloid consisting of columbamine having four extra hydrogens at positions 5, 8, 13 and 13a and (S)-configuration.		2.0210berberine alkaloid;
organic heterotetracyclic compound
dihydrochelerythrine
dihydrochelerythrine: trypanocidal and antileishmanial dihydrochelerythrine derivative from Garcinia lucida; structure in first source		3.3360benzophenanthridine alkaloid
nadp
[no description available]		2.110
8-hydroxydihydrosanguinarine
8-hydroxydihydrosanguinarine: compound with potent acetylcholinesterase inhibitory activity from Chelidonium majus L.; structure in first source		2.0510
6-methoxydihydrosanguinarine
6-methoxydihydrosanguinarine: from Corydalis tashiroi (Fumariaceae); structure in first source		2.6120
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.4110
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.		07.4110
Cancer of Pancreas
[description not available]		02.2110
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.2110
Acute Liver Injury, Drug-Induced
[description not available]		02.2110
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.2110
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