IMPPAT Phytochemical information: 
Cryptopine

Cryptopine
Summary

SMILES: COc1cc2C(=O)Cc3ccc4c(c3CN(CCc2cc1OC)C)OCO4
InChI: InChI=1S/C21H23NO5/c1-22-7-6-14-9-19(24-2)20(25-3)10-15(14)17(23)8-13-4-5-18-21(16(13)11-22)27-12-26-18/h4-5,9-10H,6-8,11-12H2,1-3H3
InChIKey: XPOJSWHIKCNLEQ-UHFFFAOYSA-N
DeepSMILES: COcccC=O)Ccccccc6CNCCc%14cc%18OC)))))))C))))OCO5
Scaffold Graph/Node/Bond level: O=C1Cc2ccc3c(c2CNCCc2ccccc21)OCO3
Scaffold Graph/Node level: OC1CC2CCC3OCOC3C2CNCCC2CCCCC12
Scaffold Graph level: CC1CC2CCC3CCCC3C2CCCCC2CCCCC12
Functional groups: cOC; cC(=O)C; CN(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protopine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Protopine alkaloids
Synonymous chemical names:
Cryptopine, cryptocavine, cryptopine
External chemical identifiers:
CID:CID_72616; ChEMBL:CHEMBL1339015; ZINC:ZINC000019632726; FDASRS:MW13X5YK4A; SureChEMBL:SCHEMBL178039; MolPort-001-742-769
Chemical structure download


Cryptopine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 369.42
Log P RDKit 2.85
Topological polar surface area (Å2) RDKit 57.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Cryptopine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.811413


Cryptopine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.48
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes