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: CO; c=O; cC(=O)O; cO; cOC; cOCOc; coc
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: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 filter RDKit Passed
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 0.1588
Xanosporic acid
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 2.0
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