IMPPAT Phytochemical information: 
5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
Summary

SMILES: Oc1cc2O[C@@H]([C@@H](Cc2c(c1)O)O)c1cc(=O)c(c2c(c1)c(cc(c2O)O)[C@H]1Oc2cc(O)cc(c2C[C@H]1O)O)O
InChI: InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22-,28-,29-/m1/s1
InChIKey: IPMYMEWFZKHGAX-ZKSIBHASSA-N
DeepSMILES: OcccO[C@@H][C@@H]Cc6cc%10)O))))O))ccc=O)cccc7)cccc6O))O)))[C@H]OcccO)ccc6C[C@H]%10O))))O)))))))))))O
Scaffold Graph/Node/Bond level: O=c1cc(C2CCc3ccccc3O2)cc2c(C3CCc4ccccc4O3)cccc2c1
Scaffold Graph/Node level: OC1CC(C2CCC3CCCCC3O2)CC2C(CCCC2C2CCC3CCCCC3O2)C1
Scaffold Graph level: CC1CC(C2CCC3CCCCC3C2)CC2C(CCCC2C2CCC3CCCCC3C2)C1
Functional groups: cO; cOC; CO; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavan-3-ols
Synonymous chemical names:
theaflavin
External chemical identifiers:
CID:CID_114777; ChEMBL:CHEMBL346119; ChEBI:CHEBI:136609; ZINC:ZINC000003978446; FDASRS:1IA46M0D13; SureChEMBL:SCHEMBL19551; MolPort-027-720-916
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 564.5
Log P RDKit 2.21
Topological polar surface area (Å2) RDKit 217.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 23
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
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 0.16
5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -9.30
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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
5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1846
ENSP00000229794MAPK14902
ENSP00000264832ICAM1800
ENSP00000311032CASP3700
ENSP00000405095TAS2R39822
ENSP00000330237CASP9700
ENSP00000263025MAPK3846
ENSP00000384273RELA800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.