IMPPAT Phytochemical information: 
Cassiamin C

Cassiamin C
Summary

SMILES: Cc1cc2c(c(c1c1c(C)cc3c(c1O)C(=O)c1c(C3=O)cccc1O)O)C(=O)c1c(C2=O)cccc1O
InChI: InChI=1S/C30H18O8/c1-11-9-15-23(29(37)21-13(25(15)33)5-3-7-17(21)31)27(35)19(11)20-12(2)10-16-24(28(20)36)30(38)22-14(26(16)34)6-4-8-18(22)32/h3-10,31-32,35-36H,1-2H3
InChIKey: VUPMYTWJSPRETC-UHFFFAOYSA-N
DeepSMILES: Ccccccc6ccC)cccc6O))C=O)ccC6=O))cccc6O))))))))))))))O))C=O)ccC6=O))cccc6O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2cc(-c3ccc4c(c3)C(=O)c3ccccc3C4=O)ccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CC(C3CCC4C(O)C5CCCCC5C(O)C4C3)CCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CC(C3CCC4C(C)C5CCCCC5C(C)C4C3)CCC12
Functional groups: cC(=O)c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
cassiamin c
External chemical identifiers:
CID:CID_442728; ChEMBL:CHEMBL516967; ChEBI:CHEBI:3455; ZINC:ZINC000004098654
Chemical structure download


Cassiamin C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.47
Log P RDKit 4.34
Topological polar surface area (Å2) RDKit 149.2
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
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 28
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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


Cassiamin C
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 Good
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 0.26


Cassiamin C
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 -5.24
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
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