IMPPAT Phytochemical information: 
Diffusarotenoid

Diffusarotenoid
Summary

SMILES: CCCCC(=O)OC1Oc2c(O)cccc2-c2c1oc1cc(O)c(cc1c2=O)C
InChI: InChI=1S/C22H20O7/c1-3-4-8-17(25)28-22-21-18(12-6-5-7-14(23)20(12)29-22)19(26)13-9-11(2)15(24)10-16(13)27-21/h5-7,9-10,22-24H,3-4,8H2,1-2H3
InChIKey: QGXIYXXRDGMFBG-UHFFFAOYSA-N
DeepSMILES: CCCCC=O)OCOccO)cccc6-cc%10occcO)ccc6c%10=O))))C
Scaffold Graph/Node/Bond level: O=c1c2c(oc3ccccc13)COc1ccccc1-2
Scaffold Graph/Node level: OC1C2CCCCC2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCCCC2CC2CCC3CCCCC3C21
Functional groups: cOC(OC(C)=O)c; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Rotenoids
Synonymous chemical names:
diffusarotenoid
External chemical identifiers:
CID:CID_100933428
Chemical structure download


Diffusarotenoid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 396.4
Log P RDKit 4.3
Topological polar surface area (Å2) RDKit 106.2
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
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 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.27
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 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


Diffusarotenoid
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 0.63


Diffusarotenoid
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 -6.03
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