IMPPAT Phytochemical information: 
Bergamottin
Bergamottin
Summary

SMILES: C/C(=C\COc1c2ccoc2cc2c1ccc(=O)o2)/CCC=C(C)C
InChI: InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
InChIKey: DBMJZOMNXBSRED-OQLLNIDSSA-N
DeepSMILES: C/C=C\COccccoc5ccc9ccc=O)o6))))))))))))))))/CCC=CC)C
Scaffold Graph/Node/Bond level: O=c1ccc2cc3ccoc3cc2o1
Scaffold Graph/Node level: OC1CCC2CC3CCOC3CC2O1
Scaffold Graph level: CC1CCC2CC3CCCC3CC2C1
Functional groups: C/C=C(\C)C; cOC; coc; c=O; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins|Simple coumarins
Synonymous chemical names:
alpha bergamottin, bergamottin(5-geranyloxy psoralen), Bergamottin, bergamotine, bergamottin, bergamotin
External chemical identifiers:
CID:CID_5471349; ChEMBL:CHEMBL1078442; ChEBI:CHEBI:70476; ZINC:ZINC000001658570; FDASRS:JMU611YFRB; SureChEMBL:SCHEMBL569529; MolPort-000-881-227
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bergamottin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.4
Log P RDKit 5.61
Topological polar surface area (Å2) RDKit 52.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
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 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
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
Bergamottin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
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 0.432794
Bergamottin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.61
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Bergamottin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000324648CYP2B6770
ENSP00000270570SLC47A1800
ENSP00000260630CYP1B1733
ENSP00000336528NR1I2727
ENSP00000242057AHR700
ENSP00000337915CYP3A4834
ENSP00000356958NR1I3700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.