IMPPAT Phytochemical information: 
10-epi-Olguine
10-epi-Olguine
Summary

SMILES: CC(=O)O[C@H]([C@H](OC(=O)C)/C=C/[C@@H]1O[C@@H]1[C@@H]1OC(=O)C=C[C@@H]1OC(=O)C)C
InChI: InChI=1S/C18H22O9/c1-9(23-10(2)19)13(24-11(3)20)5-6-15-17(26-15)18-14(25-12(4)21)7-8-16(22)27-18/h5-9,13-15,17-18H,1-4H3/b6-5+/t9-,13+,14-,15-,17-,18+/m0/s1
InChIKey: WSMOXQBLJXEQNX-GMHYHFCSSA-N
DeepSMILES: CC=O)O[C@H][C@H]OC=O)C)))/C=C/[C@@H]O[C@@H]3[C@@H]OC=O)C=C[C@@H]6OC=O)C)))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CCC(C2CO2)O1
Scaffold Graph/Node level: OC1CCCC(C2CO2)O1
Scaffold Graph level: CC1CCCC(C2CC2)C1
Functional groups: CC(=O)OC; C/C=C/[C@@H]1O[C@@H]1C; O=C1C=CCCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tetracarboxylic acids and derivatives
Synonymous chemical names:
10-epi-olguine ( 5,6-dihydro-α-pyrone)
External chemical identifiers:
CID:CID_6442294; ChEMBL:CHEMBL463301; ZINC:ZINC000033955327; SureChEMBL:SCHEMBL17616679
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
10-epi-Olguine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 382.37
Log P RDKit 0.61
Topological polar surface area (Å2) RDKit 117.73
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 10
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
10-epi-Olguine
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 0.269931
10-epi-Olguine
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 -8.28
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No