IMPPAT Phytochemical information: 
Gmelanone

Gmelanone
Summary

SMILES: O=C1[C@@H]2CO[C@]1(CO[C@@H]2c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2
InChI: InChI=1S/C20H16O7/c21-19-13-7-27-20(19,12-2-4-15-17(6-12)26-10-24-15)8-22-18(13)11-1-3-14-16(5-11)25-9-23-14/h1-6,13,18H,7-10H2/t13-,18-,20-/m1/s1
InChIKey: NNFGXXXVGRYOSF-CFSSXQINSA-N
DeepSMILES: O=C[C@@H]CO[C@]5CO[C@@H]7cccccc6)OCO5)))))))))))cccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1C2COC1(c1ccc3c(c1)OCO3)COC2c1ccc2c(c1)OCO2
Scaffold Graph/Node level: OC1C2COC1(C1CCC3OCOC3C1)COC2C1CCC2OCOC2C1
Scaffold Graph level: CC1C2CCC1(C1CCC3CCCC3C1)CCC2C1CCC2CCCC2C1
Functional groups: CC(=O)C; COC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzodioxoles
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Furofuranoid lignans
Synonymous chemical names:
gmelanone, Gmelanone
External chemical identifiers:
CID:CID_21722946; ZINC:ZINC000015262113
Chemical structure download


Gmelanone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.34
Log P RDKit 2.33
Topological polar surface area (Å2) RDKit 72.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Gmelanone
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.805494


Gmelanone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.16
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No