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; cO; coc; c=O
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, Rohitukine
External chemical identifiers:
CID:CID_13422573; ChEMBL:CHEMBL1077604; ChEBI: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 0.734864


Rohitukine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.20
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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