IMPPAT Phytochemical information: 
epi-Tulipinolide diepoxide
epi-Tulipinolide diepoxide
Summary

SMILES: CC(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2CC[C@@]2([C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)O2)C
InChI: InChI=1S/C17H22O6/c1-8-12-10(20-9(2)18)7-17(4)11(22-17)5-6-16(3)14(23-16)13(12)21-15(8)19/h10-14H,1,5-7H2,2-4H3/t10-,11-,12-,13+,14-,16-,17-/m1/s1
InChIKey: WVJZWGBZQIZLSZ-KLGRDHRDSA-N
DeepSMILES: CC=O)O[C@@H]C[C@@]C)O[C@@H]3CC[C@@][C@@H][C@@H][C@@H]%11C=C)C=O)O5)))))O3))C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C1CCC1OC1CCC1OC12
Scaffold Graph/Node level: CC1C(O)OC2C1CCC1OC1CCC1OC12
Scaffold Graph level: CC1CC2C3CC3CCC3CC3CCC2C1C
Functional groups: CC(=O)OC; C[C@H]1O[C@]1(C)C; C[C@]1(C)O[C@@H]1C; C=C1CCOC1=O
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: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
epitulipinolide diepoxide
External chemical identifiers:
CID:CID_442311; ChEBI:CHEBI:10553; ZINC:ZINC000004098200
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
epi-Tulipinolide diepoxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 322.36
Log P RDKit 1.51
Topological polar surface area (Å2) RDKit 77.66
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
epi-Tulipinolide diepoxide
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 0.41366
epi-Tulipinolide diepoxide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.34
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No