IMPPAT Phytochemical information: 
Cyclocurcumin

Cyclocurcumin
Summary

SMILES: COc1cc(/C=C/C2=CC(=O)CC(O2)c2ccc(c(c2)OC)O)ccc1O
InChI: InChI=1S/C21H20O6/c1-25-20-9-13(4-7-17(20)23)3-6-16-11-15(22)12-19(27-16)14-5-8-18(24)21(10-14)26-2/h3-11,19,23-24H,12H2,1-2H3/b6-3+
InChIKey: IZLBLUIBVMGMIY-ZZXKWVIFSA-N
DeepSMILES: COccc/C=C/C=CC=O)CCO6)cccccc6)OC)))O))))))))))))ccc6O
Scaffold Graph/Node/Bond level: O=C1C=C(C=Cc2ccccc2)OC(c2ccccc2)C1
Scaffold Graph/Node level: OC1CC(CCC2CCCCC2)OC(C2CCCCC2)C1
Scaffold Graph level: CC1CC(CCC2CCCCC2)CC(C2CCCCC2)C1
Functional groups: cOC; c/C=C/C1=CC(=O)CCO1; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Diarylheptanoids
ClassyFire Subclass: Linear diarylheptanoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Diarylheptanoids
NP Classifier Class: Linear diarylheptanoids
Synonymous chemical names:
cyclocurcumin
External chemical identifiers:
CID:CID_69879809; ChEMBL:CHEMBL4098368; ChEBI:CHEBI:175723; SureChEMBL:SCHEMBL6727064; MolPort-042-675-262
Chemical structure download


Cyclocurcumin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.39
Log P RDKit 3.74
Topological polar surface area (Å2) RDKit 85.22
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 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.19
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Cyclocurcumin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.836195


Cyclocurcumin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.42
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No