IMPPAT Phytochemical information: 
Rohitukine

Rohitukine
Summary

SMILES: CN1CC[C@@H]([C@@H](C1)O)c1c(O)cc(c2c1oc(C)cc2=O)O
InChI: InChI=1S/C16H19NO5/c1-8-5-10(18)15-12(20)6-11(19)14(16(15)22-8)9-3-4-17(2)7-13(9)21/h5-6,9,13,19-21H,3-4,7H2,1-2H3/t9-,13+/m0/s1
InChIKey: MOCVYVBNJQIVOV-TVQRCGJNSA-N
DeepSMILES: CNCC[C@@H][C@@H]C6)O))ccO)cccc6ocC)cc6=O)))))))O
Scaffold Graph/Node/Bond level: O=c1ccoc2c(C3CCNCC3)cccc12
Scaffold Graph/Node level: OC1CCOC2C1CCCC2C1CCNCC1
Scaffold Graph level: CC1CCCC2C1CCCC2C1CCCCC1
Functional groups: CN(C)C; CO; c=O; cO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Piperidines
ClassyFire Subclass: Phenylpiperidines
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Chromanes
NP Classifier Class: Chromones
Synonymous chemical names:
rohitukine
External chemical identifiers:
CID:13422573; ChEMBL:CHEMBL1077604; ChEBI:156498; SureChEMBL:SCHEMBL23718142
Chemical structure download


Rohitukine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 305.33
Log P RDKit 1.29
Topological polar surface area (Å2) RDKit 94.14
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
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 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Rohitukine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7349


Rohitukine
ADMET 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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.2
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes