IMPPAT Phytochemical information: 
Fangchinoline
Fangchinoline
Summary

SMILES: COc1cc2CCN([C@@H]3c2c(c1O)Oc1cc2c(cc1OC)CCN([C@H]2Cc1ccc(Oc2cc(C3)ccc2OC)cc1)C)C
InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m0/s1
InChIKey: IIQSJHUEZBTSAT-VMPREFPWSA-N
DeepSMILES: COcccCCN[C@@H]c6cc%10O))Occcccc6OC))))CCN[C@H]6CccccOcccC%22)ccc6OC)))))))))cc6))))))))C))))))))))))C
Scaffold Graph/Node/Bond level: c1cc2cc(c1)Oc1ccc(cc1)CC1NCCc3ccc(cc31)Oc1cccc3c1C(C2)NCC3
Scaffold Graph/Node level: C1CC2CC(C1)OC1CCC(CC1)CC1NCCC3CCC(CC31)OC1CCCC3CCNC(C2)C31
Scaffold Graph level: C1CC2CC3CCC(CC3)CC3CCCC4CCC(CC5CCCC6CCCC(CC(C1)C2)C65)CC43
Functional groups: cOC; CN(C)C; cO; cOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
(+)limacine, fangchinoline
External chemical identifiers:
CID:CID_73481; ChEMBL:CHEMBL504256; ChEBI:CHEBI:132893; ZINC:ZINC000038148193; FDASRS:953592C3ZB; SureChEMBL:SCHEMBL1460487; MolPort-020-005-723
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Fangchinoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 608.74
Log P RDKit 6.86
Topological polar surface area (Å2) RDKit 72.86
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 8
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 8
Fangchinoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.27
Fangchinoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Fangchinoline
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000227507CCND1815
ENSP00000265162ENPEP800
ENSP00000266041ITIH4800
ENSP00000283916TMPRSS11D786
ENSP00000362082CCND3819
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.