IMPPAT Phytochemical information: 
Heraclesol

Heraclesol
Summary

SMILES: COc1c(OC[C@H](C(O)(C)C)O)c2occc2c2c1ccc(=O)o2
InChI: InChI=1S/C17H18O7/c1-17(2,20)11(18)8-23-16-14(21-3)9-4-5-12(19)24-13(9)10-6-7-22-15(10)16/h4-7,11,18,20H,8H2,1-3H3/t11-/m1/s1
InChIKey: SYCQEMIWUFVJHN-LLVKDONJSA-N
DeepSMILES: COccOC[C@H]CO)C)C))O))))coccc5cc9ccc=O)o6
Scaffold Graph/Node/Bond level: O=c1ccc2ccc3occc3c2o1
Scaffold Graph/Node level: OC1CCC2CCC3OCCC3C2O1
Scaffold Graph level: CC1CCC2CCC3CCCC3C2C1
Functional groups: cOC; CO; 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:
heraclesol
External chemical identifiers:
CID:CID_15596587; ZINC:ZINC000013323045
Chemical structure download


Heraclesol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 334.32
Log P RDKit 2.06
Topological polar surface area (Å2) RDKit 102.27
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 7
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 11
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 5
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


Heraclesol
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.69


Heraclesol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -7.22
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes