IMPPAT Phytochemical information: 
Shikonin
Shikonin
Summary

SMILES: CC(=CC[C@H](C1=CC(=O)c2c(C1=O)c(O)ccc2O)O)C
InChI: InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
InChIKey: NEZONWMXZKDMKF-SNVBAGLBSA-N
DeepSMILES: CC=CC[C@H]C=CC=O)ccC6=O))cO)ccc6O))))))))))O))))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2ccccc21
Scaffold Graph/Node level: OC1CCC(O)C2CCCCC12
Scaffold Graph level: CC1CCC(C)C2CCCCC12
Functional groups: CC1=CC(=O)ccC1=O; CC=C(C)C; CO; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
arnebin-4, shikonin
External chemical identifiers:
CID:479503; ChEMBL:CHEMBL9470; ChEBI:81068; ZINC:ZINC000002015152; FDASRS:3IK6592UBW; SureChEMBL:SCHEMBL33969; MolPort-005-932-876
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Shikonin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 288.3
Log P RDKit 2.12
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Shikonin
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 0.5847
Shikonin
ADMET 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 -5.96
Number of PAINS structural alerts SwissADME 2.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Shikonin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000259808RIPK1800
ENSP00000262320AXIN1800
ENSP00000269305TP53818
ENSP00000270202AKT1816
ENSP00000293272CCL5826
ENSP00000295453ALPPL2800
ENSP00000296511ANXA5816
ENSP00000320171PKM824
ENSP00000350941SRC800
ENSP00000361021PTEN850
ENSP00000363822AR800
ENSP00000363965ALPL800
ENSP00000367851CYBB733
ENSP00000374357ARNTL800
ENSP00000375881ALPP800
ENSP00000386884CXCR4800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.