IMPPAT Phytochemical information: 
Lanatin

Lanatin
Summary

SMILES: CC(=CCOc1cc2occc2c2c1ccc(=O)o2)C
InChI: InChI=1S/C16H14O4/c1-10(2)5-7-18-13-9-14-12(6-8-19-14)16-11(13)3-4-15(17)20-16/h3-6,8-9H,7H2,1-2H3
InChIKey: KRMAZPGDYXHYMX-UHFFFAOYSA-N
DeepSMILES: CC=CCOcccoccc5cc9ccc=O)o6))))))))))))))))C
Scaffold Graph/Node/Bond level: O=c1ccc2ccc3occc3c2o1
Scaffold Graph/Node level: OC1CCC2CCC3OCCC3C2O1
Scaffold Graph level: CC1CCC2CCC3CCCC3C2C1
Functional groups: CC=C(C)C; cOC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Furanocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins
Synonymous chemical names:
Lanatin
External chemical identifiers:
CID:CID_53398715
Chemical structure download


Lanatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 270.28
Log P RDKit 3.88
Topological polar surface area (Å2) RDKit 52.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
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 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 3
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 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


Lanatin
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 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53


Lanatin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.43
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 No
P-glycoprotein substrate SwissADME No