IMPPAT Phytochemical information: 
Rubraxanthone

Rubraxanthone
Summary

SMILES: COc1c(O)cc2c(c1C/C=C(/CCC=C(C)C)\C)c(=O)c1c(o2)cc(cc1O)O
InChI: InChI=1S/C24H26O6/c1-13(2)6-5-7-14(3)8-9-16-21-20(12-18(27)24(16)29-4)30-19-11-15(25)10-17(26)22(19)23(21)28/h6,8,10-12,25-27H,5,7,9H2,1-4H3/b14-8+
InChIKey: JLTSTSRANGPLOQ-RIYZIHGNSA-N
DeepSMILES: COccO)cccc6C/C=C/CCC=CC)C)))))\C)))))c=O)cco6)cccc6O)))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: cOC; cO; C/C=C(/C)C; CC=C(C)C; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
rubraxanthone
External chemical identifiers:
CID:CID_9953366; ChEMBL:CHEMBL458846; ChEBI:CHEBI:66318; ZINC:ZINC000013393279; SureChEMBL:SCHEMBL8664946
Chemical structure download


Rubraxanthone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 410.47
Log P RDKit 5.31
Topological polar surface area (Å2) RDKit 100.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 6
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 17
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


Rubraxanthone
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.376251


Rubraxanthone
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 High
Log Kp (Skin permeation, cm/s) SwissADME -4.40
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