IMPPAT Phytochemical information: 
Cadensin D

Cadensin D
Summary

SMILES: OC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)c(OC)cc1c2oc2ccccc2c1=O
InChI: InChI=1S/C25H22O9/c1-29-16-8-12(9-17(30-2)21(16)28)22-19(11-26)33-25-23-14(10-18(31-3)24(25)34-22)20(27)13-6-4-5-7-15(13)32-23/h4-10,19,22,26,28H,11H2,1-3H3/t19-,22-/m1/s1
InChIKey: MIKIHCHUGBZLHD-DENIHFKCSA-N
DeepSMILES: OC[C@H]OccO[C@@H]6cccOC))ccc6)OC)))O)))))))cOC))ccc6occcccc6c%10=O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2c3c(ccc12)OC(c1ccccc1)CO3
Scaffold Graph/Node level: OC1C2CCCCC2OC2C1CCC1OC(C3CCCCC3)COC12
Scaffold Graph level: CC1C2CCCCC2CC2C3CCC(C4CCCCC4)CC3CCC12
Functional groups: CO; c=O; cOC; cO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzodioxanes
ClassyFire Subclass: Phenylbenzodioxanes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
hypericorin
External chemical identifiers:
CID:CID_190366; ZINC:ZINC000013381016
Chemical structure download


Cadensin D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 466.44
Log P RDKit 3.55
Topological polar surface area (Å2) RDKit 116.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.24
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 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
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


Cadensin D
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.43


Cadensin D
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 -6.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes