IMPPAT Phytochemical information: 
Hydroxysanguinarine

Hydroxysanguinarine
Summary

SMILES: Cn1c(=O)c2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2
InChI: InChI=1S/C20H13NO5/c1-21-18-12(3-2-10-6-15-16(7-13(10)18)25-8-24-15)11-4-5-14-19(26-9-23-14)17(11)20(21)22/h2-7H,8-9H2,1H3
InChIKey: UFHGABBBZRPRJV-UHFFFAOYSA-N
DeepSMILES: Cnc=O)ccOCOc5ccc9cc%13cccOCOc5cc9cc%13
Scaffold Graph/Node/Bond level: O=c1[nH]c2c3cc4c(cc3ccc2c2ccc3c(c12)OCO3)OCO4
Scaffold Graph/Node level: OC1NC2C3CC4OCOC4CC3CCC2C2CCC3OCOC3C12
Scaffold Graph level: CC1CC2C3CC4CCCC4CC3CCC2C2CCC3CCCC3C12
Functional groups: cn(C)c; c=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
oxysanguinarine, Oxysanguinarine
External chemical identifiers:
CID:CID_443716; ChEBI:CHEBI:31679; ZINC:ZINC000000900926; MolPort-046-153-795
Chemical structure download


Hydroxysanguinarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 347.33
Log P RDKit 3.3
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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


Hydroxysanguinarine
Drug-likeness properties
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 0.456908


Hydroxysanguinarine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.92
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No