IMPPAT Phytochemical information: 
Shikonofuran B

Shikonofuran B
Summary

SMILES: CCC(C(=O)OC(c1coc(c1)c1cc(O)ccc1O)CC=C(C)C)C
InChI: InChI=1S/C21H26O5/c1-5-14(4)21(24)26-19(9-6-13(2)3)15-10-20(25-12-15)17-11-16(22)7-8-18(17)23/h6-8,10-12,14,19,22-23H,5,9H2,1-4H3
InChIKey: PEZOMNLHRUVLDV-UHFFFAOYSA-N
DeepSMILES: CCCC=O)OCccocc5)cccO)ccc6O)))))))))))CC=CC)C)))))))C
Scaffold Graph/Node/Bond level: c1ccc(-c2ccco2)cc1
Scaffold Graph/Node level: C1CCC(C2CCCO2)CC1
Scaffold Graph level: C1CCC(C2CCCC2)CC1
Functional groups: COC(C)=O; coc; cO; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Benzenediols
Synonymous chemical names:
shikonofuran b, Shikonofuran B
External chemical identifiers:
CID:CID_5321287
Chemical structure download


Shikonofuran B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.43
Log P RDKit 5.34
Topological polar surface area (Å2) RDKit 79.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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


Shikonofuran B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.396367


Shikonofuran B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.92
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No