IMPPAT Phytochemical information: 
(1R,2R,3R,7S,9R,13R,14S,15R,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.02,7.03,15.07,14.013,17]heptadec-5-ene-4,11,16-trione
(1R,2R,3R,7S,9R,13R,14S,15R,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.02,7.03,15.07,14.013,17]heptadec-5-ene-4,11,16-trione
Summary

SMILES: OC[C@]12[C@@H]3OC(=O)C[C@H]1[C@]1([C@@]4(C3)[C@]3([C@@H]2C(=O)[C@@]1([C@@]3(O)C(=O)C=C4C)O)C)C
InChI: InChI=1S/C20H22O7/c1-8-4-10(22)19(25)16(3)13-14(24)20(19,26)15(2)9-5-12(23)27-11(6-18(8,15)16)17(9,13)7-21/h4,9,11,13,21,25-26H,5-7H2,1-3H3/t9-,11+,13-,15-,16+,17+,18-,19+,20+/m0/s1
InChIKey: QUDGSOQXSJGXMH-HDFMWDNXSA-N
DeepSMILES: OC[C@][C@@H]OC=O)C[C@H]6[C@][C@@]C8)[C@][C@@H]%10C=O)[C@@]6[C@@]5O)C=O)C=C9C)))))O))))C)))C
Scaffold Graph/Node/Bond level: O=C1CC2C3C(CC45C=CC(=O)C6C(C(=O)C3C64)C25)O1
Scaffold Graph/Node level: OC1CC2C3C(CC45CCC(O)C6C(C(O)C3C64)C25)O1
Scaffold Graph level: CC1CC2CC34CCC(C)C5C6C(C)C(C2C(C1)C63)C54
Functional groups: CO; CC(=O)OC; CC(=O)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:
shinjulactone c
External chemical identifiers:
CID:CID_71717359; ZINC:ZINC000095593940
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,3R,7S,9R,13R,14S,15R,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.02,7.03,15.07,14.013,17]heptadec-5-ene-4,11,16-trione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 374.39
Log P RDKit -0.48
Topological polar surface area (Å2) RDKit 121.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 6
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
(1R,2R,3R,7S,9R,13R,14S,15R,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.02,7.03,15.07,14.013,17]heptadec-5-ene-4,11,16-trione
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 1
Ghose rule RDKit Failed
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 0.53
(1R,2R,3R,7S,9R,13R,14S,15R,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.02,7.03,15.07,14.013,17]heptadec-5-ene-4,11,16-trione
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 -9.56
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes