IMPPAT Phytochemical information: 
Desoxyshikonin

Desoxyshikonin
Summary

SMILES: CC(=CC[C@H](C1CC(=O)c2c(C1)c(O)ccc2O)O)C
InChI: InChI=1S/C16H20O4/c1-9(2)3-4-12(17)10-7-11-13(18)5-6-14(19)16(11)15(20)8-10/h3,5-6,10,12,17-19H,4,7-8H2,1-2H3/t10?,12-/m1/s1
InChIKey: XDIFJVFIEIJYNB-TVKKRMFBSA-N
DeepSMILES: CC=CC[C@H]CCC=O)ccC6)cO)ccc6O))))))))))O))))C
Scaffold Graph/Node/Bond level: O=C1CCCc2ccccc21
Scaffold Graph/Node level: OC1CCCC2CCCCC12
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: CC=C(C)C; cC(=O)C; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Tetralins
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Meromonoterpenoids
Synonymous chemical names:
desoxyshikonin
External chemical identifiers:
CID:CID_129711776
Chemical structure download


Desoxyshikonin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 276.33
Log P RDKit 2.56
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
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


Desoxyshikonin
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 0.585429


Desoxyshikonin
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 -5.78
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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