IMPPAT Phytochemical information: 
12-beta-(Benzoyloxy)daphnetoxin
12-beta-(Benzoyloxy)daphnetoxin
Summary

SMILES: OC[C@]12O[C@H]1[C@H]1[C@H]3O[C@@]4(O[C@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)C(=C1)C)[C@@H]([C@H]([C@@]3(O4)C(=C)C)OC(=O)c1ccccc1)C)c1ccccc1
InChI: InChI=1S/C34H34O10/c1-17(2)32-25(40-28(37)20-11-7-5-8-12-20)19(4)33-22-15-18(3)24(36)31(22,39)29(38)30(16-35)26(41-30)23(33)27(32)42-34(43-32,44-33)21-13-9-6-10-14-21/h5-15,19,22-23,25-27,29,35,38-39H,1,16H2,2-4H3/t19-,22-,23+,25-,26+,27-,29-,30+,31-,32+,33+,34+/m1/s1
InChIKey: QKMXESBAFIKRAD-LPHDITAFSA-N
DeepSMILES: OC[C@]O[C@H]3[C@H][C@H]O[C@@]O[C@]6[C@H][C@@][C@@H]%12O))O)C=O)C=C5)C)))))[C@@H][C@H][C@@]8O7)C=C)C)))OC=O)cccccc6)))))))))C))))cccccc6
Scaffold Graph/Node/Bond level: O=C(OC1CC23OC4(c5ccccc5)OC1C(O4)C2C1OC1CC1C(=O)C=CC13)c1ccccc1
Scaffold Graph/Node level: OC1CCC2C1CC1OC1C1C3OC4(C5CCCCC5)OC3C(OC(O)C3CCCCC3)CC21O4
Scaffold Graph level: CC(CC1CC23CC4(C5CCCCC5)CC1C(C4)C2C1CC1CC1C(C)CCC13)C1CCCCC1
Functional groups: CO; C[C@]1(C)O[C@H]1C; c[C@@]1(OC)OCCO1; CC1=CCCC1=O; C=C(C)C; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Daphnane diterpenoids
Synonymous chemical names:
genkwadaphnin
External chemical identifiers:
CID:CID_124210
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
12-beta-(Benzoyloxy)daphnetoxin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 602.64
Log P RDKit 2.17
Topological polar surface area (Å2) RDKit 144.28
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
12-beta-(Benzoyloxy)daphnetoxin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.264655
12-beta-(Benzoyloxy)daphnetoxin
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 No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.03
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes