IMPPAT Phytochemical information: 
Pendulinine

Pendulinine
Summary

SMILES: COc1cc2CCN(C3c2c2c1Oc1c(O2)c(O)cc2c1[C@H](Cc1ccc(c(c1)Oc1ccc(C3)cc1)O)N(CC2)C)C
InChI: InChI=1S/C35H34N2O6/c1-36-13-11-22-18-29(40-3)33-35-31(22)24(36)14-19-4-7-23(8-5-19)41-28-16-20(6-9-26(28)38)15-25-30-21(10-12-37(25)2)17-27(39)32(42-35)34(30)43-33/h4-9,16-18,24-25,38-39H,10-15H2,1-3H3/t24?,25-/m0/s1
InChIKey: SAOOVIWEVMRLNC-BBMPLOMVSA-N
DeepSMILES: COcccCCNCc6cc%10OccO6)cO)ccc6[C@H]Ccccccc6)OccccC%24)cc6))))))))O))))))NCC6))C))))))))))))))C
Scaffold Graph/Node/Bond level: c1cc2cc(c1)Oc1ccc(cc1)CC1NCCc3ccc4c(c31)Oc1ccc3c(c1O4)C(C2)NCC3
Scaffold Graph/Node level: C1CC2CC(C1)OC1CCC(CC1)CC1NCCC3CCC4OC5C(CCC6CCNC(C2)C65)OC4C31
Scaffold Graph level: C1CC2CC3CCC(CC3)CC3CCCC4CCC5CC6C(CCC7CCCC(CC(C1)C2)C76)CC5C43
Functional groups: cOC; cO; CN(C)C; 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
Synonymous chemical names:
pendulinine
External chemical identifiers:
CID:CID_101422869
Chemical structure download


Pendulinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 578.67
Log P RDKit 6.65
Topological polar surface area (Å2) RDKit 83.86
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 43
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 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 7
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 11
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 11


Pendulinine
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 0.23


Pendulinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.82
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