IMPPAT Phytochemical information: 
Bracteatin 6-glucoside
Bracteatin 6-glucoside
Summary

SMILES: OCC1O[C@@H](Oc2cc3OC(=Cc4cc(O)c(c(c4)O)O)C(=O)c3c(c2)O)C([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H20O12/c22-6-14-18(28)19(29)20(30)21(33-14)31-8-4-9(23)15-12(5-8)32-13(17(15)27)3-7-1-10(24)16(26)11(25)2-7/h1-5,14,18-26,28-30H,6H2/t14?,18-,19+,20?,21-/m1/s1
InChIKey: SFXSFWVZPKEDPA-YHYCZKRCSA-N
DeepSMILES: OCCO[C@@H]OcccOC=CcccO)ccc6)O))O))))))C=O)c5cc9)O))))))))))C[C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C(=Cc2ccccc2)Oc2cc(OC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1C(CC2CCCCC2)OC2CC(OC3CCCCO3)CCC21
Scaffold Graph level: CC1C(CC2CCCCC2)CC2CC(CC3CCCCC3)CCC21
Functional groups: CO; cO[C@@H](C)OC; cC=C1OccC1=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Aurones
Synonymous chemical names:
bracteatin 6-glucoside
External chemical identifiers:
CID:CID_42607774
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bracteatin 6-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 464.38
Log P RDKit -0.7
Topological polar surface area (Å2) RDKit 206.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
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 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Bracteatin 6-glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.208866
Bracteatin 6-glucoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.73
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes