IMPPAT Phytochemical information: 
Rosicine

Rosicine
Summary

SMILES: COC(=O)C1=C2Nc3c(C42[C@@H]2[C@H](C1)[C@@H]1O[C@@H]1CN2CC4)cccc3
InChI: InChI=1S/C19H20N2O3/c1-23-18(22)11-8-10-15-14(24-15)9-21-7-6-19(17(10)21)12-4-2-3-5-13(12)20-16(11)19/h2-5,10,14-15,17,20H,6-9H2,1H3/t10-,14-,15+,17+,19?/m1/s1
InChIKey: YTUCJPLHEFJMQN-KVSAPGQISA-N
DeepSMILES: COC=O)C=CNccC5[C@@H][C@H]C9)[C@@H]O[C@@H]3CN7CC%10))))))))))cccc6
Scaffold Graph/Node/Bond level: C1=C2Nc3ccccc3C23CCN2CC4OC4C(C1)C23
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3C4OC4CN4CCC12C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC3C4CC4CC4CCC12C43
Functional groups: cNC(=C(C(=O)OC)C)C; C[C@H]1O[C@H]1C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
rosicine
Chemical structure download


Rosicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.38
Log P RDKit 1.65
Topological polar surface area (Å2) RDKit 54.1
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Rosicine
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 0.628789


Rosicine
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 -7.01
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No