IMPPAT Phytochemical information: 
Xanosporic acid
Xanosporic acid
Summary

SMILES: COc1c(CC(O)C)c2c3c(CC(O)C)c(oc4c3c3c5c2c(c1O)c(=O)cc5OCOc3cc4O)C(=O)O
InChI: InChI=1S/C28H24O11/c1-9(29)4-11-17-18-12(5-10(2)30)26(28(34)35)39-27-14(32)7-16-21(23(18)27)20-15(37-8-38-16)6-13(31)19(22(17)20)24(33)25(11)36-3/h6-7,9-10,29-30,32-33H,4-5,8H2,1-3H3,(H,34,35)
InChIKey: UMSMIPFQWKRZKC-UHFFFAOYSA-N
DeepSMILES: COccCCO)C)))cccCCO)C)))cocc6ccc%10cc%14O))c=O)cc6OCOc%11cc%15O)))))))))))))))))C=O)O
Scaffold Graph/Node/Bond level: O=c1cc2c3c4c(ccc5occc(c6cccc1c63)c54)OCO2
Scaffold Graph/Node level: OC1CC2OCOC3CCC4OCCC5C6CCCC1C6C2C3C45
Scaffold Graph level: CC1CC2CCCC3CCC4CCCC5C6CCCC1C6C2C3C45
Functional groups: cOC; cO; cC(=O)O; CO; coc; c=O; cOCOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Phenanthrols
NP Classifier Biosynthetic pathway: Polyketides
Synonymous chemical names:
tinosporic acid, xanosporic acid
External chemical identifiers:
CID:CID_46879540
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Xanosporic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 536.49
Log P RDKit 3.38
Topological polar surface area (Å2) RDKit 176.12
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 5
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
Xanosporic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.16
Xanosporic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately 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 -7.31
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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