IMPPAT Phytochemical information: 
Chanoclavine

Chanoclavine
Summary

SMILES: CN[C@@H]1Cc2c[nH]c3c2c([C@H]1/C=C(/CO)\C)ccc3
InChI: InChI=1S/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+/t13-,15-/m1/s1
InChIKey: SAHHMCVYMGARBT-HEESEWQSSA-N
DeepSMILES: CN[C@@H]Ccc[nH]cc5c[C@H]9/C=C/CO))\C))))ccc6
Scaffold Graph/Node/Bond level: c1cc2c3c(c[nH]c3c1)CCC2
Scaffold Graph/Node level: C1CC2CCCC3NCC(C1)C23
Scaffold Graph level: C1CC2CCCC3CCC(C1)C23
Functional groups: CNC; c[nH]c; C/C(C)=C/C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ergoline and derivatives
ClassyFire Subclass: Clavines and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Ergot alkaloids
Synonymous chemical names:
chanoclavines i, Chanoclavine, chanoclavine, chanoclavin-i
External chemical identifiers:
CID:CID_5281381; ChEBI:CHEBI:3576; FDASRS:32X6F73RE2
Chemical structure download


Chanoclavine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 256.35
Log P RDKit 2.33
Topological polar surface area (Å2) RDKit 48.05
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Chanoclavine
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 0.738188


Chanoclavine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.31
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes