IMPPAT Phytochemical information: 
Uncinatone

Uncinatone
Summary

SMILES: C[C@H]1Cc2c(O1)c(O)c1c(c2O)C(=O)C=C2[C@]1(C)CCC(=C2C)C
InChI: InChI=1S/C20H22O4/c1-9-5-6-20(4)13(11(9)3)8-14(21)15-16(20)18(23)19-12(17(15)22)7-10(2)24-19/h8,10,22-23H,5-7H2,1-4H3/t10-,20-/m0/s1
InChIKey: IQGPVLVWUUPQMQ-FVINQWEUSA-N
DeepSMILES: C[C@H]CccO5)cO)ccc6O))C=O)C=C[C@]6C)CCC=C6C))C
Scaffold Graph/Node/Bond level: O=C1C=C2C=CCCC2c2cc3c(cc21)CCO3
Scaffold Graph/Node level: OC1CC2CCCCC2C2CC3OCCC3CC12
Scaffold Graph level: CC1CC2CCCCC2C2CC3CCCC3CC12
Functional groups: cOC; cO; cC(=O)C=C(C)C(C)=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Abeoabietane diterpenoids|Furanoabietane diterpenoids
Synonymous chemical names:
Uncinatone, uncinatone
External chemical identifiers:
CID:CID_442547; ChEMBL:CHEMBL4159483; ChEBI:CHEBI:9861; ZINC:ZINC000004098464; SureChEMBL:SCHEMBL4743868; MolPort-039-338-328
Chemical structure download


Uncinatone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.39
Log P RDKit 3.93
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4


Uncinatone
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 0.708932


Uncinatone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.74
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes