IMPPAT Phytochemical information: 
9,10-Dihydroxy-5-(4-hydroxy-2-methoxyphenyl)-6-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-dimethoxybenzo[a]xanthen-2-one
9,10-Dihydroxy-5-(4-hydroxy-2-methoxyphenyl)-6-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-dimethoxybenzo[a]xanthen-2-one
Summary

SMILES: COc1cc(O)ccc1c1c(Cc2ccc(c(c2)OC)O)c2oc3cc(O)c(cc3cc2c2c1cc(OC)c(=O)c2OC)O
InChI: InChI=1S/C34H28O10/c1-40-27-13-18(35)6-7-19(27)30-20-14-29(42-3)32(39)34(43-4)31(20)22-11-17-12-24(37)25(38)15-26(17)44-33(22)21(30)9-16-5-8-23(36)28(10-16)41-2/h5-8,10-15,35-38H,9H2,1-4H3
InChIKey: WLDGLUYONPYMAV-UHFFFAOYSA-N
DeepSMILES: COcccO)ccc6ccCcccccc6)OC)))O))))))cocccO)ccc6cc%10cc%14ccOC))c=O)c6OC))))))))))))O
Scaffold Graph/Node/Bond level: O=c1ccc2c(-c3ccccc3)c(Cc3ccccc3)c3oc4ccccc4cc3c2c1
Scaffold Graph/Node level: OC1CCC2C(C1)C1CC3CCCCC3OC1C(CC1CCCCC1)C2C1CCCCC1
Scaffold Graph level: CC1CCC2C(C1)C1CC3CCCCC3CC1C(CC1CCCCC1)C2C1CCCCC1
Functional groups: cOC; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Diarylheptanoids
ClassyFire Subclass: Linear diarylheptanoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
Santalin B, santalin b
External chemical identifiers:
CID:CID_5490285
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9,10-Dihydroxy-5-(4-hydroxy-2-methoxyphenyl)-6-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-dimethoxybenzo[a]xanthen-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 596.59
Log P RDKit 6.21
Topological polar surface area (Å2) RDKit 148.05
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 29
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 5
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 6
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
9,10-Dihydroxy-5-(4-hydroxy-2-methoxyphenyl)-6-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-dimethoxybenzo[a]xanthen-2-one
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 4
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 0.095167
9,10-Dihydroxy-5-(4-hydroxy-2-methoxyphenyl)-6-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-dimethoxybenzo[a]xanthen-2-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.08
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No