IMPPAT Phytochemical information: 
Ipobscurine B
Ipobscurine B
Summary

SMILES: OC[C@@H]([C@@H](c1ccc(c(c1)OC)O)O)Oc1ccc2c(c1)c(CCNC(=O)/C=C/c1ccc(cc1)O)c[nH]2
InChI: InChI=1S/C29H30N2O7/c1-37-26-14-19(5-10-25(26)34)29(36)27(17-32)38-22-8-9-24-23(15-22)20(16-31-24)12-13-30-28(35)11-4-18-2-6-21(33)7-3-18/h2-11,14-16,27,29,31-34,36H,12-13,17H2,1H3,(H,30,35)/b11-4+/t27-,29+/m0/s1
InChIKey: LMWMSKRQOYZVFO-SWBAOWADSA-N
DeepSMILES: OC[C@@H][C@@H]cccccc6)OC)))O)))))O))Occcccc6)cCCNC=O)/C=C/cccccc6))O)))))))))))c[nH]5
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)NCCc1c[nH]c2ccc(OCCc3ccccc3)cc12
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCCC1CNC2CCC(OCCC3CCCCC3)CC12
Scaffold Graph level: CC(CCCC1CCC2CCC(CCCC3CCCCC3)CC12)CCC1CCCCC1
Functional groups: CO; cO; c[nH]c; cOC; c/C=C/C(=O)NC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acid amides
Synonymous chemical names:
ipobscurine b
External chemical identifiers:
CID:CID_5318459; ZINC:ZINC000033831933
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ipobscurine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 518.57
Log P RDKit 3.43
Topological polar surface area (Å2) RDKit 144.27
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 23
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
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
Ipobscurine B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.166949
Ipobscurine B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.21
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No