IMPPAT Phytochemical information: 
Graminone b
Graminone b
Summary

SMILES: COc1cc(O)cc(c1)[C@@H]1OC[C@@H]2[C@H]1C(=O)O[C@H]2c1cc(O)c(c(c1)OC)OC
InChI: InChI=1S/C21H22O8/c1-25-13-5-10(4-12(22)8-13)19-17-14(9-28-19)18(29-21(17)24)11-6-15(23)20(27-3)16(7-11)26-2/h4-8,14,17-19,22-23H,9H2,1-3H3/t14-,17-,18+,19+/m1/s1
InChIKey: JTDVCRMQMDJLOR-OAOYMFHYSA-N
DeepSMILES: COcccO)ccc6)[C@@H]OC[C@@H][C@H]5C=O)O[C@H]5cccO)ccc6)OC)))OC
Scaffold Graph/Node/Bond level: O=C1OC(c2ccccc2)C2COC(c3ccccc3)C12
Scaffold Graph/Node level: OC1OC(C2CCCCC2)C2COC(C3CCCCC3)C12
Scaffold Graph level: CC1CC(C2CCCCC2)C2CCC(C3CCCCC3)C12
Functional groups: cOC; cO; COC; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Stilbenoids|Lignans
NP Classifier Class: Furofuranoid lignans|Stilbenolignans
Synonymous chemical names:
graminone b
External chemical identifiers:
CID:CID_10001150; ChEMBL:CHEMBL460859; ChEBI:CHEBI:65979; ZINC:ZINC000040393518
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Graminone b
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 402.4
Log P RDKit 2.73
Topological polar surface area (Å2) RDKit 103.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Graminone b
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73613
Graminone b
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.33
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes