IMPPAT Phytochemical information: 
Iguesterin

Iguesterin
Summary

SMILES: CC1=CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CC=C4C3=CC(=O)C(=C4C)O)[C@]1(CC2)C)C)C
InChI: InChI=1S/C28H36O2/c1-17-9-10-25(3)11-13-27(5)22-8-7-19-18(2)24(30)21(29)16-20(19)26(22,4)12-14-28(27,6)23(25)15-17/h7-9,16,23,30H,10-15H2,1-6H3/t23-,25-,26+,27-,28+/m1/s1
InChIKey: FLMDVQMCMIGPEK-IPTPSVHJSA-N
DeepSMILES: CC=CC[C@][C@@H]C6)[C@]C)CC[C@@]C=CC=CC6=CC=O)C=C6C))O))))))))[C@]6CC%10))C)))C))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2=CC=C3C(CCC4C3CCC3CC=CCC34)C2=C1
Scaffold Graph/Node level: OC1CCC2CCC3C(CCC4C5CCCCC5CCC43)C2C1
Scaffold Graph level: CC1CCC2CCC3C(CCC4C5CCCCC5CCC43)C2C1
Functional groups: CC=C(C)C; CC1=C(O)C(=O)C=C2CC(=CC=C21)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
Synonymous chemical names:
iguesterin
External chemical identifiers:
CID:CID_46881919; ChEMBL:CHEMBL1092796; SureChEMBL:SCHEMBL20988640
Chemical structure download


Iguesterin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 404.59
Log P RDKit 7.16
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.61
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Iguesterin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
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 0.434771


Iguesterin
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 -4.44
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No