IMPPAT Phytochemical information: 
(S)-Scoulerine
(S)-Scoulerine
Summary

SMILES: COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3)c(O)c(cc1)OC
InChI: InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
InChIKey: KNWVMRVOBAFFMH-HNNXBMFYSA-N
DeepSMILES: COcccCCN[C@H]c6cc%10O))))CccC6)cO)ccc6))OC
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1c3ccccc3CCN1C2
Scaffold Graph/Node level: C1CCC2CN3CCC4CCCCC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4CCCCC43)CC2C1
Functional groups: cOC; CN(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Protoberberine alkaloids
Synonymous chemical names:
(-)scoulerine, (-)-scoulerine, (s)-scoulerine, scoulerine, aequaline, Scoulerine
External chemical identifiers:
CID:CID_439654; ChEMBL:CHEMBL1235966; ChEBI:CHEBI:17129; ZINC:ZINC000028465419; SureChEMBL:SCHEMBL679505; MolPort-046-153-752
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(S)-Scoulerine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 327.38
Log P RDKit 2.77
Topological polar surface area (Å2) RDKit 62.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
(S)-Scoulerine
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 0.88799
(S)-Scoulerine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.46
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
(S)-Scoulerine
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_000752ENSG00000142192APP351BindingDB, ChEMBL
TAR_EXP_001885ENSG00000178999AURKB9212ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_001767ENSG00000132906CASP9842BindingDB
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL, NPASS
TAR_EXP_001574ENSG00000087586AURKA6790ChEMBL
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL, NPASS
TAR_EXP_001373ENSG00000239713APOBEC3G60489ChEMBL, NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001076ENSG00000111802TDP251567BindingDB, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL, NPASS
TAR_EXP_000696ENSG00000120868APAF1317BindingDB, ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB
TAR_EXP_000325ENSG00000149295DRD21813BindingDB, ChEMBL, NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000361ENSG00000128394APOBEC3F200316NPASS