IMPPAT Phytochemical information: 
Balsaminone B
Balsaminone B
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c(OC)c3c4C(=O)c5ccccc5C(=O)c4oc3c3c2cccc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H22O10/c1-34-26-17-16-18(29)11-6-2-3-7-12(11)19(30)25(16)36-23(17)13-8-4-5-9-14(13)24(26)37-27-22(33)21(32)20(31)15(10-28)35-27/h2-9,15,20-22,27-28,31-33H,10H2,1H3/t15-,20-,21+,22-,27+/m1/s1
InChIKey: NAVQPSCNRHEZLY-FPISNOLNSA-N
DeepSMILES: OC[C@H]O[C@@H]OccOC))ccC=O)cccccc6C=O)c%10oc%13cc%17cccc6))))))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2c1oc1c2cc(OC2CCCCO2)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2C3CC(OC4CCCCO4)C4CCCCC4C3OC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2C1CC1C3CCCCC3C(CC3CCCCC3)CC12
Functional groups: CO; cO[C@@H](C)OC; cOC; cC(=O)c; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
Synonymous chemical names:
balsaminone-b
External chemical identifiers:
CID:CID_10815442; ChEMBL:CHEMBL463739; ZINC:ZINC000044387644
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Balsaminone B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.46
Log P RDKit 1.55
Topological polar surface area (Å2) RDKit 155.89
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Balsaminone B
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 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.28
Balsaminone B
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 No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.49
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No