IMPPAT Phytochemical information: 
Cryptopleurine

Cryptopleurine
Summary

SMILES: COc1ccc2c(c1)c1cc(OC)c(cc1c1c2CN2CCCC[C@@H]2C1)OC
InChI: InChI=1S/C24H27NO3/c1-26-16-7-8-17-19(11-16)21-13-24(28-3)23(27-2)12-20(21)18-10-15-6-4-5-9-25(15)14-22(17)18/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m1/s1
InChIKey: RSHYSOGXGSUUIJ-OAHLLOKOSA-N
DeepSMILES: COcccccc6)cccOC))ccc6cc%10CNCCCC[C@@H]6C%10))))))))))))OC
Scaffold Graph/Node/Bond level: c1ccc2c(c1)c1c(c3ccccc32)CN2CCCCC2C1
Scaffold Graph/Node level: C1CCC2C(C1)C1CCCCC1C1CN3CCCCC3CC21
Scaffold Graph level: C1CCC2CC3C4CCCCC4C4CCCCC4C3CC2C1
Functional groups: CN(C)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Phenanthroquinolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Indolizidine alkaloids
Synonymous chemical names:
Cryptopleurine, cryptopleurine
External chemical identifiers:
CID:CID_92765; ChEMBL:CHEMBL198075; ChEBI:CHEBI:3932; ZINC:ZINC000004098776; FDASRS:3JZK58H75B; SureChEMBL:SCHEMBL12780396; MolPort-047-659-651
Chemical structure download


Cryptopleurine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 377.48
Log P RDKit 4.93
Topological polar surface area (Å2) RDKit 30.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Cryptopleurine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.605786


Cryptopleurine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.97
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Cryptopleurine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000353104DHDDS705
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.