IMPPAT Phytochemical information: 
Maesopsin

Maesopsin
Summary

SMILES: Oc1ccc(cc1)CC1(O)Oc2c(C1=O)c(O)cc(c2)O
InChI: InChI=1S/C15H12O6/c16-9-3-1-8(2-4-9)7-15(20)14(19)13-11(18)5-10(17)6-12(13)21-15/h1-6,16-18,20H,7H2
InChIKey: LOFYFDPXORJJEE-UHFFFAOYSA-N
DeepSMILES: Occcccc6))CCO)OccC5=O))cO)ccc6)O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2OC1Cc1ccccc1
Scaffold Graph/Node level: OC1C(CC2CCCCC2)OC2CCCCC21
Scaffold Graph level: CC1C(CC2CCCCC2)CC2CCCCC21
Functional groups: cO; CC1(O)OccC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Aurone flavonoids
ClassyFire Subclass: Auronols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Aurones
Synonymous chemical names:
Maesopsin, maesopsin
External chemical identifiers:
CID:CID_160803; ChEMBL:CHEMBL462109; SureChEMBL:SCHEMBL9957960
Chemical structure download


Maesopsin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 288.26
Log P RDKit 1.31
Topological polar surface area (Å2) RDKit 107.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.13
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Maesopsin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.663447


Maesopsin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes