IMPPAT Phytochemical information: 
Bisisodiospyrin
Bisisodiospyrin
Summary

SMILES: O=C1C(=CC(=O)c2c1c(O)c(c(c2)C)c1c(C)cc(c2c1C(=O)C=CC2=O)O)C1=CC(=O)c2c(C1=O)c(O)c(c(c2)C)c1c(C)cc(c2c1C(=O)C=CC2=O)O
InChI: InChI=1S/C44H26O12/c1-15-9-21-27(49)13-19(41(53)35(21)43(55)33(15)31-17(3)11-29(51)37-23(45)5-7-25(47)39(31)37)20-14-28(50)22-10-16(2)34(44(56)36(22)42(20)54)32-18(4)12-30(52)38-24(46)6-8-26(48)40(32)38/h5-14,51-52,55-56H,1-4H3
InChIKey: HIBRRCAYIWFCBY-UHFFFAOYSA-N
DeepSMILES: O=CC=CC=O)cc6cO)ccc6)C))ccC)cccc6C=O)C=CC6=O)))))))O)))))))))))C=CC=O)ccC6=O))cO)ccc6)C))ccC)cccc6C=O)C=CC6=O)))))))O
Scaffold Graph/Node/Bond level: O=C1C=C(C2=CC(=O)c3ccc(-c4cccc5c4C(=O)C=CC5=O)cc3C2=O)C(=O)c2cc(-c3cccc4c3C(=O)C=CC4=O)ccc21
Scaffold Graph/Node level: OC1CC(C2CC(O)C3CCC(C4CCCC5C(O)CCC(O)C54)CC3C2O)C(O)C2CC(C3CCCC4C(O)CCC(O)C43)CCC12
Scaffold Graph level: CC1CC(C2CC(C)C3CCC(C4CCCC5C(C)CCC(C)C54)CC3C2C)C(C)C2CC(C3CCCC4C(C)CCC(C)C43)CCC12
Functional groups: O=C1C=C(C2=CC(=O)ccC2=O)C(=O)cc1; cO; O=C1C=CC(=O)cc1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
bisisodiospyrin
External chemical identifiers:
CID:CID_169144
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bisisodiospyrin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 746.68
Log P RDKit 6.26
Topological polar surface area (Å2) RDKit 217.48
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 56
Number of heteroatoms RDKit 12
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 40
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 8
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 8
Bisisodiospyrin
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 4
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 0.18
Bisisodiospyrin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -5.76
Number of PAINS structural alerts SwissADME 1
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 Yes