IMPPAT Phytochemical information: 
Isopenniclavine

Isopenniclavine
Summary

SMILES: OC[C@]1(O)CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3
InChI: InChI=1S/C16H18N2O2/c1-18-8-16(20,9-19)6-12-11-3-2-4-13-15(11)10(7-17-13)5-14(12)18/h2-4,6-7,14,17,19-20H,5,8-9H2,1H3/t14-,16-/m1/s1
InChIKey: KCHBNRCSCHMJFD-GDBMZVCRSA-N
DeepSMILES: OC[C@]O)CNC)[C@H]C=C6)cccccc6cC%10)c[nH]5
Scaffold Graph/Node/Bond level: C1=C2c3cccc4[nH]cc(c34)CC2NCC1
Scaffold Graph/Node level: C1CNC2CC3CNC4CCCC(C2C1)C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CCCC2C31
Functional groups: CO; CN(C)C; cC(=CC)C; c[nH]c
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:
isopenniclavine
External chemical identifiers:
CID:CID_12311156; ZINC:ZINC000033832021; FDASRS:957F5HGG0I
Chemical structure download


Isopenniclavine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 270.33
Log P RDKit 1.14
Topological polar surface area (Å2) RDKit 59.49
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
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 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
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


Isopenniclavine
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 0.73


Isopenniclavine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.19
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes