IMPPAT Phytochemical information: 
(2Z)-6-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one
(2Z)-6-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)cc3c2C(=O)/C(=C/c2cc(O)c(c(c2)O)O)/O3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H20O12/c22-6-14-18(28)19(29)20(30)21(33-14)32-12-5-8(23)4-11-15(12)17(27)13(31-11)3-7-1-9(24)16(26)10(25)2-7/h1-5,14,18-26,28-30H,6H2/b13-3-/t14-,18-,19+,20-,21-/m1/s1
InChIKey: CNLUHMGCIFZWFM-KJOZQHLTSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6C=O)/C=C/cccO)ccc6)O))O))))))/O5))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C(=Cc2ccccc2)Oc2cccc(OC3CCCCO3)c21
Scaffold Graph/Node level: OC1C(CC2CCCCC2)OC2CCCC(OC3CCCCO3)C21
Scaffold Graph level: CC1C(CC2CCCCC2)CC2CCCC(CC3CCCCC3)C21
Functional groups: CO; cO[C@@H](C)OC; cO; c/C=C1\OccC1=O
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:
bractein
External chemical identifiers:
CID:CID_14430150
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2Z)-6-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one
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
(2Z)-6-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.21
(2Z)-6-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one
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 -9.12
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 No