IMPPAT Phytochemical information: 
Kesselringine

Kesselringine
Summary

SMILES: CO[C@]12Oc3c(O)cc4c5c3[C@@](C1)(CC[C@H]5NCC4)CC[C@H]2O
InChI: InChI=1S/C18H23NO4/c1-22-18-9-17(6-3-13(18)21)5-2-11-14-10(4-7-19-11)8-12(20)16(23-18)15(14)17/h8,11,13,19-21H,2-7,9H2,1H3/t11-,13-,17+,18+/m1/s1
InChIKey: LEFDMAOTHOSJAA-MBUVNVKMSA-N
DeepSMILES: CO[C@]OccO)cccc6[C@@]C%10)CC[C@H]6NCC%10))))))CC[C@H]%12O
Scaffold Graph/Node/Bond level: c1cc2c3c4c1CCNC4CCC31CCCC(C1)O2
Scaffold Graph/Node level: C1CC2CC3(C1)CCC1NCCC4CCC(O2)C3C41
Scaffold Graph level: C1CC2CCC3CC4CCCC5(CCC(C1)C2C35)C4
Functional groups: cO[C@@](OC)(C)C; cO; CNC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
kesselringine
External chemical identifiers:
CID:CID_76967674; FDASRS:E941TI35EP
Chemical structure download


Kesselringine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 317.39
Log P RDKit 1.89
Topological polar surface area (Å2) RDKit 70.95
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Kesselringine
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74


Kesselringine
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 -7.27
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes