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, Helenalin
External chemical identifiers:
CID:CID_23205; ChEMBL:CHEMBL338474; ChEBI: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
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 0.526862
Helenalin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.47
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 No
Helenalin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001236ENSG00000185386MAPK115600ChEMBL
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001239ENSG00000156711MAPK135603ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053ChEMBL, NPASS
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_001467ENSG00000188130MAPK126300ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001599ENSG00000164362TERT7015ChEMBL, NPASS
TAR_EXP_001645ENSG00000105397TYK27297ChEMBL, NPASS
TAR_EXP_000969ENSG00000077150NFKB24791ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001892ENSG00000135898GPR559290BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_001677ENSG00000100219XBP17494BindingDB, ChEMBL, NPASS
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_001366ENSG00000117152RGS45999ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_000867ENSG00000135679MDM24193BindingDB, ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185BindingDB, ChEMBL, NPASS
TAR_EXP_000333ENSG00000134817APLNR187BindingDB
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000003ENSG00000278570NR2E310002ChEMBL, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088ChEMBL, NPASS
TAR_EXP_000785ENSG00000105639JAK33718ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740ChEMBL, NPASS
TAR_EXP_000783ENSG00000162434JAK13716ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000683ENSG00000197386HTT3064ChEMBL, NPASS
TAR_EXP_000784ENSG00000096968JAK23717ChEMBL, NPASS