IMPPAT Phytochemical information: 
(1S,2S,4S,5R,10R,11S,13S,14R,15R,18S)-15-[(1S)-1-[(1S,4R,6S)-1,6-dimethyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-5,13-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
(1S,2S,4S,5R,10R,11S,13S,14R,15R,18S)-15-[(1S)-1-[(1S,4R,6S)-1,6-dimethyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-5,13-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
Summary

SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@@H]2O[C@@H]2[C@@]2([C@]1(C)C(=O)C=CC2)O)[C@@H]1OC(=O)[C@@]2([C@@](C1)(C)O2)C
InChI: InChI=1S/C28H38O7/c1-13(17-12-24(2)27(5,35-24)23(31)33-17)14-8-9-15-20-16(11-19(30)25(14,15)3)26(4)18(29)7-6-10-28(26,32)22-21(20)34-22/h6-7,13-17,19-22,30,32H,8-12H2,1-5H3/t13-,14+,15-,16-,17+,19-,20-,21-,22-,24-,25+,26-,27+,28-/m0/s1
InChIKey: UZLXIIADBIXQHY-JNUSPZCGSA-N
DeepSMILES: C[C@@H][C@H]CC[C@@H][C@]5C)[C@@H]O)C[C@H][C@H]6[C@@H]O[C@@H]3[C@@][C@]7C)C=O)C=CC6)))))O))))))))))))))[C@@H]OC=O)[C@@][C@@]C6)C)O3))C
Scaffold Graph/Node/Bond level: O=C1OC(CC2CCC3C2CCC2C4C(=O)C=CCC4C4OC4C32)CC2OC12
Scaffold Graph/Node level: OC1CCCC2C3OC3C3C4CCC(CC5CC6OC6C(O)O5)C4CCC3C12
Scaffold Graph level: CC1CC(CC2CCC3C2CCC2C4C(C)CCCC4C4CC4C32)CC2CC12
Functional groups: C[C@]12CCOC(=O)[C@@]1(C)O2; CO; C[C@@H]1O[C@@H]1C; CC=CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
daturalactone
External chemical identifiers:
CID:CID_21607604; ZINC:ZINC000073371237
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,2S,4S,5R,10R,11S,13S,14R,15R,18S)-15-[(1S)-1-[(1S,4R,6S)-1,6-dimethyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-5,13-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 486.61
Log P RDKit 2.56
Topological polar surface area (Å2) RDKit 108.89
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
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 3
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
(1S,2S,4S,5R,10R,11S,13S,14R,15R,18S)-15-[(1S)-1-[(1S,4R,6S)-1,6-dimethyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-5,13-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
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 2
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 0.456091
(1S,2S,4S,5R,10R,11S,13S,14R,15R,18S)-15-[(1S)-1-[(1S,4R,6S)-1,6-dimethyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-5,13-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
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 -7.33
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