IMPPAT Phytochemical information: 
Artemisin

Artemisin
Summary

SMILES: O[C@H]1C[C@@]2(C)C=CC(=O)C(=C2[C@@H]2[C@@H]1[C@H](C)C(=O)O2)C
InChI: InChI=1S/C15H18O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h4-5,8,10-11,13,17H,6H2,1-3H3/t8-,10-,11+,13-,15+/m0/s1
InChIKey: LUHMMHZLDLBAKX-DBIGVJDZSA-N
DeepSMILES: O[C@H]C[C@@]C)C=CC=O)C=C6[C@@H][C@@H]%10[C@H]C)C=O)O5))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2CCC3CC(=O)OC3C2=C1
Scaffold Graph/Node level: OC1CCC2CCC3CC(O)OC3C2C1
Scaffold Graph level: CC1CCC2CCC3CC(C)CC3C2C1
Functional groups: CO; CC1=C(C)CC=CC1=O; COC(=O)C
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: Eudesmane sesquiterpenoids
Synonymous chemical names:
alpha-hydroxysantonin, 7-hydroxysantonin (artemisin), artemisin
External chemical identifiers:
CID:CID_65030; ChEMBL:CHEMBL158124; ChEBI:CHEBI:2852; FDASRS:Y1R67R7XWU; SureChEMBL:SCHEMBL83537
Chemical structure download


Artemisin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.31
Log P RDKit 1.39
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 5
Stereochemical complexity RDKit 0.33
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


Artemisin
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 0.670034


Artemisin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.09
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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


Artemisin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000342007CYP1A2700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.