IMPPAT Phytochemical information: 
(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Summary

SMILES: COc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)C1[C@H]1[C@H](Oc2c(C1=O)c(O)cc(c2)O)c1ccc(cc1)OC)O
InChI: InChI=1S/C32H26O10/c1-39-19-7-3-15(4-8-19)31-27(29(37)25-21(35)11-17(33)13-23(25)41-31)28-30(38)26-22(36)12-18(34)14-24(26)42-32(28)16-5-9-20(40-2)10-6-16/h3-14,27-28,31-36H,1-2H3/t27-,28?,31-,32-/m1/s1
InChIKey: BTCICADMSGBCKA-VGVWILAUSA-N
DeepSMILES: COcccccc6))[C@H]OcccO)ccc6C=O)C%10[C@H][C@H]OccC6=O))cO)ccc6)O)))))))cccccc6))OC)))))))))))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2OC(c2ccccc2)C1C1C(=O)c2ccccc2OC1c1ccccc1
Scaffold Graph/Node level: OC1C2CCCCC2OC(C2CCCCC2)C1C1C(O)C2CCCCC2OC1C1CCCCC1
Scaffold Graph level: CC1C2CCCCC2CC(C2CCCCC2)C1C1C(C)C2CCCCC2CC1C1CCCCC1
Functional groups: cO; cOC; cC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Biflavonoids and polyflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
chamaejasmenin b
External chemical identifiers:
CID:CID_16745525; ChEMBL:CHEMBL1545093
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 570.55
Log P RDKit 5.09
Topological polar surface area (Å2) RDKit 151.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 26
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 5
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
(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Drug-likeness
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 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25525
(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.03
Number of PAINS structural alerts SwissADME 0
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
(2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000683ENSG00000197386HTT3064NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000614ENSG00000087460GNAS2778NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_001551ENSG00000145335SNCA6622NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_001677ENSG00000100219XBP17494BindingDB, NPASS