IMPPAT Phytochemical information: 
Cycloheterophyllin
Cycloheterophyllin
Summary

SMILES: CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1oc1-c3cc(O)c(cc3OC(c1c2=O)C=C(C)C)O)O)C
InChI: InChI=1S/C30H30O7/c1-14(2)7-8-17-27-16(9-10-30(5,6)37-27)25(33)24-26(34)23-22(11-15(3)4)35-21-13-20(32)19(31)12-18(21)29(23)36-28(17)24/h7,9-13,22,31-33H,8H2,1-6H3
InChIKey: ZZPIXEJZTXAVCX-UHFFFAOYSA-N
DeepSMILES: CC=CCccOCC)C)C=Cc6ccc%10oc-cccO)ccc6OCc%10c%14=O)))C=CC)C)))))))O)))))))))O)))))))))))C
Scaffold Graph/Node/Bond level: O=c1c2c(oc3cc4c(cc13)C=CCO4)-c1ccccc1OC2
Scaffold Graph/Node level: OC1C2CC3CCCOC3CC2OC2C3CCCCC3OCC12
Scaffold Graph level: CC1C2CC3CCCCC3CC2CC2C3CCCCC3CCC12
Functional groups: CC=C(C)C; cO; cOC; cC=CC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Pyranoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
Cycloheterophyllin, cycloheterophyllin
External chemical identifiers:
CID:CID_5316250; ChEMBL:CHEMBL461820; ChEBI:CHEBI:175844; MolPort-035-706-553
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cycloheterophyllin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 502.56
Log P RDKit 6.67
Topological polar surface area (Å2) RDKit 109.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
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 1
Stereochemical complexity RDKit 0.03
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 3
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5
Cycloheterophyllin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.271015
Cycloheterophyllin
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 -4.56
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No