IMPPAT Phytochemical information: 
Heterophyllin

Heterophyllin
Summary

SMILES: CC(=CCc1c(oc2c(c1=O)c(O)c1c(c2CC=C(C)C)OC(C=C1)(C)C)c1cc(O)c(cc1O)O)C
InChI: InChI=1S/C30H32O7/c1-15(2)7-9-17-25(34)24-26(35)18-11-12-30(5,6)37-28(18)19(10-8-16(3)4)29(24)36-27(17)20-13-22(32)23(33)14-21(20)31/h7-8,11-14,31-33,35H,9-10H2,1-6H3
InChIKey: CBYLXVCMCVXUQQ-UHFFFAOYSA-N
DeepSMILES: CC=CCccoccc6=O))cO)ccc6CC=CC)C)))))OCC=C6))C)C)))))))))cccO)ccc6O)))O)))))))))C
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2cc3c(cc12)C=CCO3
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC3OCCCC3CC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC3CCCCC3CC12
Functional groups: CC=C(C)C; cO; coc; c=O; cOC; cC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
heterophyllin
External chemical identifiers:
CID:CID_14557105; ChEMBL:CHEMBL461821; ChEBI:CHEBI:171988; ZINC:ZINC000015273917
Chemical structure download


Heterophyllin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 504.58
Log P RDKit 6.48
Topological polar surface area (Å2) RDKit 120.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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


Heterophyllin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.18


Heterophyllin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.34
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Heterophyllin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000447803DDIT3816
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.