IMPPAT Phytochemical information: 
Citrunobin
Citrunobin
Summary

SMILES: COc1cc(O)c(c2c1C=CC(O2)(C)C)C(=O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C21H20O5/c1-21(2)11-10-15-18(25-3)12-17(24)19(20(15)26-21)16(23)9-6-13-4-7-14(22)8-5-13/h4-12,22,24H,1-3H3/b9-6+
InChIKey: RPGWAGOTDRYEAD-RMKNXTFCSA-N
DeepSMILES: COcccO)ccc6C=CCO6)C)C))))))C=O)/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)c1cccc2c1OCC=C2
Scaffold Graph/Node level: OC(CCC1CCCCC1)C1CCCC2CCCOC21
Scaffold Graph level: CC(CCC1CCCCC1)C1CCCC2CCCCC21
Functional groups: cOC; cO; cC=CC; c/C=C/C(c)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Linear 1,3-diarylpropanoids
ClassyFire Subclass: Chalcones and dihydrochalcones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Chalcones
Synonymous chemical names:
citrunobin
External chemical identifiers:
CID:CID_14542258; ChEBI:CHEBI:175512; ZINC:ZINC000013398289
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Citrunobin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.39
Log P RDKit 4.19
Topological polar surface area (Å2) RDKit 75.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
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 17
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 4
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
Citrunobin
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.637407
Citrunobin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.30
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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