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: CC=C(C)C; CC1=CC(=O)ccC1=O; 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, shikonin
External chemical identifiers:
CID:CID_479503; ChEMBL:CHEMBL9470; ChEBI: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
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 0.584707
Shikonin
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 -5.96
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 2
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
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_001770ENSG00000167780SOAT28435NPASS
TAR_EXP_001805ENSG00000159216RUNX1861ChEMBL
TAR_EXP_001810ENSG00000067955CBFB865ChEMBL, NPASS
TAR_EXP_001935ENSG00000164045CDC25A993ChEMBL, NPASS
TAR_EXP_001937ENSG00000101224CDC25B994ChEMBL, NPASS
TAR_EXP_001939ENSG00000158402CDC25C995ChEMBL
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL, NPASS
TAR_EXP_001619ENSG00000131747TOP2A7153ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL, NPASS
TAR_EXP_001620ENSG00000077097TOP2B7155ChEMBL, NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001737ENSG00000145391SETD780854ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068ChEMBL, NPASS
TAR_EXP_001552ENSG00000057252SOAT16646ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_001128ENSG00000067225PKM5315ChEMBL, NPASS
TAR_EXP_001127ENSG00000262785PKLR5313ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_001306ENSG00000196396PTPN15770ChEMBL, NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS