IMPPAT Phytochemical information: 
13-Oxocryptopine
13-Oxocryptopine
Summary

SMILES: COc1cc2c(cc1OC)CCN(C)Cc1c(C(=O)C2=O)ccc2c1OCO2
InChI: InChI=1S/C21H21NO6/c1-22-7-6-12-8-17(25-2)18(26-3)9-14(12)20(24)19(23)13-4-5-16-21(15(13)10-22)28-11-27-16/h4-5,8-9H,6-7,10-11H2,1-3H3
InChIKey: UFCVPEFVGGMGSE-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC))))CCNC)CccC=O)C%10=O)))cccc6OCO5
Scaffold Graph/Node/Bond level: O=C1C(=O)c2ccc3c(c2CNCCc2ccccc21)OCO3
Scaffold Graph/Node level: OC1C(O)C2CCC3OCOC3C2CNCCC2CCCCC21
Scaffold Graph level: CC1C(C)C2CCC3CCCC3C2CCCCC2CCCCC21
Functional groups: cOC; CN(C)C; cC(=O)C(=O)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:
13-oxocryptopine
External chemical identifiers:
CID:CID_131751339; ZINC:ZINC000013411454
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
13-Oxocryptopine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 383.4
Log P RDKit 2.49
Topological polar surface area (Å2) RDKit 74.3
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
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 14
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.33
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
13-Oxocryptopine
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 0.737797
13-Oxocryptopine
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 -6.84
Number of PAINS structural alerts SwissADME 1
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