IMPPAT Phytochemical information: 
Tyloindicine B

Tyloindicine B
Summary

SMILES: COc1ccc(cc1O)C1=C(CN2[C@@](C1)(C)CCC2)c1cccc(c1)OC(=O)C
InChI: InChI=1S/C24H27NO4/c1-16(26)29-19-7-4-6-17(12-19)21-15-25-11-5-10-24(25,2)14-20(21)18-8-9-23(28-3)22(27)13-18/h4,6-9,12-13,27H,5,10-11,14-15H2,1-3H3/t24-/m0/s1
InChIKey: NXAUETMHJIPRPU-DEOSSOPVSA-N
DeepSMILES: COcccccc6O)))C=CCN[C@@]C6)C)CCC5))))))cccccc6)OC=O)C
Scaffold Graph/Node/Bond level: c1ccc(C2=C(c3ccccc3)CN3CCCC3C2)cc1
Scaffold Graph/Node level: C1CCC(C2CC3CCCN3CC2C2CCCCC2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCC3CC2C2CCCCC2)CC1
Functional groups: cOC; cO; cC(=C(c)C)C; CN(C)C; cOC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
tyloindicine b, Tyloindicine B
External chemical identifiers:
CID:CID_101831586; ZINC:ZINC000014824724
Chemical structure download


Tyloindicine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 393.48
Log P RDKit 4.5
Topological polar surface area (Å2) RDKit 59
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Tyloindicine B
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


Tyloindicine B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.27
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes