IMPPAT Phytochemical information: 
Isorotundifoline

Isorotundifoline
Summary

SMILES: CO/C=C(\[C@H]1C[C@@H]2N(C[C@@H]1CC)CC[C@@]12C(=O)Nc2c1c(O)ccc2)/C(=O)OC
InChI: InChI=1S/C22H28N2O5/c1-4-13-11-24-9-8-22(19-16(23-21(22)27)6-5-7-17(19)25)18(24)10-14(13)15(12-28-2)20(26)29-3/h5-7,12-14,18,25H,4,8-11H2,1-3H3,(H,23,27)/b15-12+/t13-,14-,18-,22-/m0/s1
InChIKey: IXWWTVSMMIIIFZ-JCIDKMOXSA-N
DeepSMILES: CO/C=C\[C@H]C[C@@H]NC[C@@H]6CC))))CC[C@]5C=O)Ncc5cO)ccc6)))))))))))))))/C=O)OC
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CCN1CCCCC12
Scaffold Graph/Node level: OC1NC2CCCCC2C12CCN1CCCCC12
Scaffold Graph level: CC1CC2CCCCC2C12CCC1CCCCC12
Functional groups: CO/C=C(\C)C(=O)OC; CN(C)C; cNC(=O)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type|Simple oxindole alkaloids
Synonymous chemical names:
isorotundifoline
External chemical identifiers:
CID:CID_102232176; ZINC:ZINC000033833533
Chemical structure download


Isorotundifoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 400.48
Log P RDKit 2.41
Topological polar surface area (Å2) RDKit 88.1
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Isorotundifoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.46


Isorotundifoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.36
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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