IMPPAT Phytochemical information: 
Skimmin

Skimmin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C15H16O8/c16-6-10-12(18)13(19)14(20)15(23-10)21-8-3-1-7-2-4-11(17)22-9(7)5-8/h1-5,10,12-16,18-20H,6H2/t10-,12-,13+,14-,15-/m1/s1
InChIKey: VPAOSFFTKWUGAD-TVKJYDDYSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6)oc=O)cc6))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2ccc(OC3CCCCO3)cc2o1
Scaffold Graph/Node level: OC1CCC2CCC(OC3CCCCO3)CC2O1
Scaffold Graph level: CC1CCC2CCC(CC3CCCCC3)CC2C1
Functional groups: CO; cO[C@@H](C)OC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Coumarin glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
Skimmin, skimmin
External chemical identifiers:
CID:CID_99693; ChEMBL:CHEMBL526377; ZINC:ZINC000001559620; FDASRS:H072F03PQN; SureChEMBL:SCHEMBL1944336; MolPort-000-881-167
Chemical structure download


Skimmin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 324.29
Log P RDKit -1.03
Topological polar surface area (Å2) RDKit 129.59
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 8
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 9
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Skimmin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53


Skimmin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.78
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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