IMPPAT Phytochemical information: 
Sorgolactone

Sorgolactone
Summary

SMILES: O=C1O[C@H]2[C@@H](/C/1=C\O[C@@H]1OC(=O)C(=C1)C)CC1=C2[C@@H](C)CCC1
InChI: InChI=1S/C18H20O5/c1-9-4-3-5-11-7-12-13(18(20)23-16(12)15(9)11)8-21-14-6-10(2)17(19)22-14/h6,8-9,12,14,16H,3-5,7H2,1-2H3/b13-8+/t9-,12+,14+,16-/m0/s1
InChIKey: KHSREFIWULNDAB-YCUBLIQYSA-N
DeepSMILES: O=CO[C@H][C@@H]/C/5=C\O[C@@H]OC=O)C=C5)C))))))))CC=C5[C@@H]C)CCC6
Scaffold Graph/Node/Bond level: O=C1C=CC(OC=C2C(=O)OC3C4=C(CCCC4)CC23)O1
Scaffold Graph/Node level: OC1CCC(OCC2C(O)OC3C4CCCCC4CC23)O1
Scaffold Graph level: CC1CCC(CCC2C(C)CC3C4CCCCC4CC23)C1
Functional groups: CC1=C[C@H](O/C=C2\CCOC2=O)OC1=O; CC(=C(C)C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Apocarotenoids (β-)
Synonymous chemical names:
sorgalactone
External chemical identifiers:
CID:CID_5281395; ChEMBL:CHEMBL2270920; ChEBI:CHEBI:9205; ZINC:ZINC000004097948; FDASRS:Z0IL7QT5MJ; SureChEMBL:SCHEMBL13857702; MolPort-042-644-281
Chemical structure download


Sorgolactone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.35
Log P RDKit 2.78
Topological polar surface area (Å2) RDKit 61.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
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 4


Sorgolactone
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 0.34


Sorgolactone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -6.67
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No