IMPPAT Phytochemical information: 
3'-Prenylrubranine
3'-Prenylrubranine
Summary

SMILES: CC(=CCc1c(O)c(C(=O)/C=C/c2ccccc2)c2c3c1O[C@]1(C)CC[C@@H]([C@@H]3C1)C(O2)(C)C)C
InChI: InChI=1S/C30H34O4/c1-18(2)11-13-20-26(32)25(23(31)14-12-19-9-7-6-8-10-19)28-24-21-17-30(5,34-27(20)24)16-15-22(21)29(3,4)33-28/h6-12,14,21-22,32H,13,15-17H2,1-5H3/b14-12+/t21-,22-,30+/m0/s1
InChIKey: FYCUILMSDSLIGD-NLBJBFNFSA-N
DeepSMILES: CC=CCccO)cC=O)/C=C/cccccc6)))))))))ccc6O[C@]C)CC[C@@H][C@@H]8C6))CO%10)C)C)))))))))))))))C
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)c1ccc2c3c1OCC1CCC(CC31)O2
Scaffold Graph/Node level: OC(CCC1CCCCC1)C1CCC2OC3CCC4COC1C2C4C3
Scaffold Graph level: CC(CCC1CCCCC1)C1CCC2CC3CCC4CCC1C2C4C3
Functional groups: CC=C(C)C; cO; c/C=C/C(c)=O; cOC
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:
3'-prenylrubranine, 3’-prenylrubranine
External chemical identifiers:
CID:CID_42607682; ZINC:ZINC000102943711
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3'-Prenylrubranine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 458.6
Log P RDKit 7
Topological polar surface area (Å2) RDKit 55.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
3'-Prenylrubranine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3
3'-Prenylrubranine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.89
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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