IMPPAT Phytochemical information: 
Cyclointegrin

Cyclointegrin
Summary

SMILES: COc1cc(O)c2c(c1)oc1-c3ccc(cc3OC(CCc1c2=O)(C)C)O
InChI: InChI=1S/C21H20O6/c1-21(2)7-6-14-19(24)18-15(23)9-12(25-3)10-17(18)26-20(14)13-5-4-11(22)8-16(13)27-21/h4-5,8-10,22-23H,6-7H2,1-3H3
InChIKey: LRBWGBCDUCRXLG-UHFFFAOYSA-N
DeepSMILES: COcccO)ccc6)oc-cccccc6OCCCc%12c%16=O)))))C)C)))))O
Scaffold Graph/Node/Bond level: O=c1c2c(oc3ccccc13)-c1ccccc1OCCC2
Scaffold Graph/Node level: OC1C2CCCCC2OC2C3CCCCC3OCCCC12
Scaffold Graph level: CC1C2CCCCC2CC2C3CCCCC3CCCCC12
Functional groups: cOC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
cyclointegrin
External chemical identifiers:
CID:CID_44258672; ChEBI:CHEBI:175721
Chemical structure download


Cyclointegrin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.39
Log P RDKit 3.98
Topological polar surface area (Å2) RDKit 89.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
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 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
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 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


Cyclointegrin
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.68


Cyclointegrin
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.72
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No