IMPPAT Phytochemical information: 
(1S,4S,5R,6R,7R,8R,13S,17S,18S,19R)-8-[(Z)-3,4-dimethylpent-2-enyl]-4,5,17-trihydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
(1S,4S,5R,6R,7R,8R,13S,17S,18S,19R)-8-[(Z)-3,4-dimethylpent-2-enyl]-4,5,17-trihydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
Summary

SMILES: C/C(=C/C[C@H]1C(=O)OC2[C@]34[C@@H]1[C@@H](C)[C@@H](O)[C@]([C@@H]4[C@@]1([C@@H](C2)C(=CC(=O)[C@H]1O)C)C)(OC3)O)/C(C)C
InChI: InChI=1S/C27H38O7/c1-12(2)13(3)7-8-16-20-15(5)21(29)27(32)24-25(6)17(14(4)9-18(28)22(25)30)10-19(34-23(16)31)26(20,24)11-33-27/h7,9,12,15-17,19-22,24,29-30,32H,8,10-11H2,1-6H3/b13-7-/t15-,16-,17+,19?,20-,21-,22-,24-,25-,26+,27-/m1/s1
InChIKey: OLLSASRUNICQER-TVAMVDQESA-N
DeepSMILES: C/C=C/C[C@H]C=O)OC[C@@][C@@H]6[C@@H]C)[C@@H]O)[C@][C@@H]6[C@@][C@@H]C%10)C=CC=O)[C@H]6O))))C)))C)))OC7))O))))))))))))/CC)C
Scaffold Graph/Node/Bond level: O=C1C=CC2CC3OC(=O)CC4CCC5OCC43C5C2C1
Scaffold Graph/Node level: OC1CCC2CC3OC(O)CC4CCC5OCC43C5C2C1
Scaffold Graph level: CC1CCC2CC3CC(C)CC4CCC5CCC43C5C2C1
Functional groups: C/C=C(/C)C; COC(=O)C; CO; CO[C@@](O)(C)C; CC(=CC(=O)C)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: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
quecellin
External chemical identifiers:
CID:CID_5459060
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,4S,5R,6R,7R,8R,13S,17S,18S,19R)-8-[(Z)-3,4-dimethylpent-2-enyl]-4,5,17-trihydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 474.59
Log P RDKit 2.38
Topological polar surface area (Å2) RDKit 113.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(1S,4S,5R,6R,7R,8R,13S,17S,18S,19R)-8-[(Z)-3,4-dimethylpent-2-enyl]-4,5,17-trihydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
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 1
Ghose filter RDKit Failed
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 0.425148
(1S,4S,5R,6R,7R,8R,13S,17S,18S,19R)-8-[(Z)-3,4-dimethylpent-2-enyl]-4,5,17-trihydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.49
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