IMPPAT Phytochemical information: 
Sanguinarine
Sanguinarine
Summary

SMILES: C[n+]1cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2
InChI: 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
DeepSMILES: C[n+]cccOCOc5ccc9cc%13cccOCOc5cc9cc%13
Scaffold Graph/Node/Bond level: c1cc2c(c[nH+]c3c4cc5c(cc4ccc23)OCO5)c2c1OCO2
Scaffold Graph/Node level: C1OC2CC3CCC4C5CCC6OCOC6C5CNC4C3CC2O1
Scaffold Graph level: C1CC2CC3CCC4C(CCC5C6CCCC6CCC54)C3CC2C1
Functional groups: c[n+](C)c; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Benzophenanthridine alkaloids
ClassyFire Subclass: Quaternary benzophenanthridine alkaloids
Synonymous chemical names:
sanguinarine, Sanguinarine
External chemical identifiers:
CID:CID_5154; ChEMBL:CHEMBL417799; ChEBI:CHEBI:17183; ZINC:ZINC000000000706; FDASRS:AV9VK043SS; SureChEMBL:SCHEMBL123241; MolPort-002-526-863
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sanguinarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.34
Log P RDKit 3.43
Topological polar surface area (Å2) RDKit 40.8
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Sanguinarine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36537
Sanguinarine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.17
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Sanguinarine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000830ENSG00000105486LIG13978BindingDB
TAR_EXP_000845ENSG00000166949SMAD34088ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000436ENSG00000171564FGB2244BindingDB, NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000499ENSG00000108839ALOX12239ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247ChEMBL, NPASS
TAR_EXP_000505ENSG00000198793MTOR2475NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000573ENSG00000091844RGS1726575ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744ChEMBL, NPASS
TAR_EXP_000612ENSG00000127955GNAI12770ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_001943ENSG00000070831CDC42998BindingDB
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001868ENSG00000036672USP29099NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001630ENSG00000074319TSG1017251NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001607ENSG00000090534THPO7066ChEMBL, NPASS
TAR_EXP_001570ENSG00000166888STAT66778ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_001368ENSG00000159788RGS126002ChEMBL, NPASS
TAR_EXP_001366ENSG00000117152RGS45999ChEMBL, NPASS
TAR_EXP_001364ENSG00000171552BCL2L1598BindingDB
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL, NPASS
TAR_EXP_001339ENSG00000136238RAC15879BindingDB
TAR_EXP_001288ENSG00000002330BAD572ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001128ENSG00000067225PKM5315ChEMBL, NPASS
TAR_EXP_000969ENSG00000077150NFKB24791ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000683ENSG00000197386HTT3064ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS