Natural Product (NP) Details

General Information of the NP (ID: NP1687)
Name
Sanguinarine
Synonyms
SANGUINARINE; 2447-54-3; Sanguinarin; Pseudochelerythrine; sangvinarin; Veadent; SANGUINARIUM; Viadent; Dimethylenedioxy benzphenanthridine; UNII-AV9VK043SS; Pseudochelerythrine;Sanguinarin; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-; Benzophenanthridine alkaloid; AV9VK043SS; CHEBI:17183; NCGC00015959-03; Sanguiritrin; CAS-2447-54-3; DSSTox_CID_25204; DSSTox_RID_80748; DSSTox_GSID_45204; 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene; 13-Methyl[1,3]benzodioxolo[5,6-C][1,3]dioxolo[4,5-I]phenanthridin-13-Ium; 13-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium; C20H14NO4; EINECS 219-503-3; BRN 3915507; Sangrovit; y-Chelerythrine; SR-01000075650; sanguinarium-chloride; Spectrum_000259; Prestwick0_000987; Prestwick1_000987; Prestwick2_000987; Prestwick3_000987; Spectrum2_000724; Spectrum3_001148; Spectrum4_001838; Spectrum5_000635; Lopac-S-5890; cid_5154; C20H14NO4Cl; Lopac0_001108; BSPBio_001053; BSPBio_002675; KBioGR_002542; KBioSS_000739; ZINC706; MLS002154085; DivK1c_000495; SCHEMBL123241; SPBio_000648; SPBio_002954; BPBio1_001159; CHEMBL417799; DTXSID0045204; SCHEMBL17131945; BDBM25525; GTPL11563; KBio1_000495; KBio2_000739; KBio2_003307; KBio2_005875; KBio3_002175; NINDS_000495; HMS1571E15; HMS2098E15; BCP13614; EX-A5014; HY-N0052; Tox21_110268; 4022AH; NSC765394; s9032; AKOS025311557; Tox21_110268_1; CCG-205184; compound 1 [PMID: 28621943]; CS-3818; NSC-765394; SDCCGMLS-0066612.P001; IDI1_000495; NCGC00015959-01; NCGC00015959-02; NCGC00015959-04; NCGC00015959-05; NCGC00015959-09; NCGC00015959-16; NCGC00160289-01; NCGC00160289-02; M892; SMR001233394; SBI-0051077.P003; DB-046461; AB00053789; FT-0634289; N1338; C06162; AB00053789_04; 447S543; Q347392; Q-100313; SR-01000075650-7; BRD-K66898851-001-03-7; 5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+); 13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium; (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl- (9CI); 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium nitrate; 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9CI; 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium; 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),23-nonaen-24-ium; 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),9,11,14,16,21,23-nonaen-24-ium; 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.0^{2,10.0^{4,8.0^{14,22.0^{17,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene; UI5
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Species Origin Bocconia frutescens ...     Click to Show/Hide
Bocconia frutescens
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Papaveraceae
Genus: Bocconia
Species: Bocconia frutescens
Disease Dental disease [ICD-11: DA08] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.975
 
MDCK Permeability
 -4.711
 
PAMPA
 +
 
HIA
 - - -
 
Distribution
VDss
 0.104
 
PPB
 65.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 +++
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 +++
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 +++
CYP2C8 inhibitor
 - - -
HLM Stability
 - -
 
Excretion
CLplasma
 2.912
 
T1/2
 0.558
Toxicity
DILI
 ++
 
Rat Oral Acute Toxicity
 ++
 
FDAMDD
 +++
 
Respiratory
 +++
 
Human Hepatotoxicity
 - -
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 -
 
Hematotoxicity
 - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C20H14NO4+
PubChem CID
5154
Canonical SMILES
C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
InChI
1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
InChIKey
INVGWHRKADIJHF-UHFFFAOYSA-N
CAS Number
CAS 2447-54-3
ChEBI ID
CHEBI:17183
Herb ID
HBIN043028
SymMap ID
SMIT00109
TCMSP ID
MOL001474
TTD Drug ID
D0T3NB
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model A2780/S CVCL_4863 Ovarian endometrioid adenocarcinoma Homo sapiens
A2780/R CVCL_4862 Ovarian endometrioid adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Sanguinarine reversed cisplatin resistance in A2780/R cells through intracellular GSH depletion.
    β. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Streptomycin + Edetic acid     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Escherichia coli Microorganism model Escherichia coli
Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
                    Experimental
                    Result(s)		 Three-drug combination of sanguinarine + EDTA + streptomycin showed synergistic activity against almost all the strains, as well as a strong reduction in the effective doses of sanguinarine, EDTA and streptomycin.
Target and Pathway
Target(s) Sodium/potassium ATPase (SPT ATPase)  Molecule Info  [4]
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Sanguinarine enhances cisplatin sensitivity via glutathione depletion in cisplatin-resistant ovarian cancer (A2780) cells. Chem Biol Drug Des. 2020 Feb;95(2):215-223.
Reference 3 Synergistic antibacterial activity of the combination of the alkaloid sanguinarine with EDTA and the antibiotic streptomycin against multidrug resistant bacteria. J Pharm Pharmacol. 2015 Feb;67(2):264-73.
Reference 4 Medicinal plants in therapy. Bull World Health Organ. 1985;63(6):965-81.
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