IMPPAT Phytochemical information: 
Helenalin
Helenalin
Summary

SMILES: C=C1C(=O)O[C@H]2[C@@H]1[C@H](O)[C@]1(C)C(=O)C=C[C@H]1[C@@H](C2)C
InChI: InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
InChIKey: ZVLOPMNVFLSSAA-XEPQRQSNSA-N
DeepSMILES: C=CC=O)O[C@H][C@@H]5[C@H]O)[C@]C)C=O)C=C[C@H]5[C@@H]C%10)C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2CCC3C=CC(=O)C3CC12
Scaffold Graph/Node level: CC1C(O)OC2CCC3CCC(O)C3CC21
Scaffold Graph level: CC1CC2CCC3CCC(C)C3CC2C1C
Functional groups: C=C1CCOC1=O; CO; O=C1C=CCC1
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: Pseudoguaiane sesquiterpenoids
Synonymous chemical names:
helenalin
External chemical identifiers:
CID:23205; ChEMBL:CHEMBL338474; ChEBI:5635; ZINC:ZINC000004098120; FDASRS:4GUY9L896T; SureChEMBL:SCHEMBL161593; MolPort-044-561-384
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Helenalin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.31
Log P RDKit 1.25
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Helenalin
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5269
Helenalin
ADMET 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.47
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Helenalin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216797NFKBIA837
ENSP00000276449STAR800
ENSP00000294728VCAM1800
ENSP00000310219HSPA6800
ENSP00000329967TBK1800
ENSP00000330237CASP9786
ENSP00000353483MAPK8826
ENSP00000384273RELA938
ENSP00000425107ATG12800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.