IMPPAT Phytochemical information: 
8-Deoxy-11,13-dihydroxygrosheimin

8-Deoxy-11,13-dihydroxygrosheimin
Summary

SMILES: OCC1(O)C(=O)OC2C1CCC(=C)C1C2C(C)C(=O)C1
InChI: InChI=1S/C15H20O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-10,12-13,16,19H,1,3-6H2,2H3
InChIKey: XJUFXNXZZRHROZ-UHFFFAOYSA-N
DeepSMILES: OCCO)C=O)OCC5CCC=C)CC7CC)C=O)C5
Scaffold Graph/Node/Bond level: C=C1CCC2CC(=O)OC2C2CC(=O)CC12
Scaffold Graph/Node level: CC1CCC2CC(O)OC2C2CC(O)CC12
Scaffold Graph level: CC1CC2CCC(C)C3CC(C)CC3C2C1
Functional groups: CO; COC(=O)C; C=C(C)C; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Guaiane sesquiterpenoids
Synonymous chemical names:
8-deoxy-11,13-dihydroxygrosheimin
External chemical identifiers:
CID:CID_5260103; ChEBI:CHEBI:168729; SureChEMBL:SCHEMBL12459119
Chemical structure download


8-Deoxy-11,13-dihydroxygrosheimin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.32
Log P RDKit 0.44
Topological polar surface area (Å2) RDKit 83.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


8-Deoxy-11,13-dihydroxygrosheimin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.54


8-Deoxy-11,13-dihydroxygrosheimin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.67
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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