IMPPAT Phytochemical information: 
Portulic lactone

Portulic lactone
Summary

SMILES: OC/C=C(/CC[C@@]1(CO)[C@H](C)C[C@@]23[C@@H]1CCC[C@@](C2)(OC3=O)C)\CO
InChI: InChI=1S/C20H32O5/c1-14-10-20-12-18(2,25-17(20)24)7-3-4-16(20)19(14,13-23)8-5-15(11-22)6-9-21/h6,14,16,21-23H,3-5,7-13H2,1-2H3/b15-6-/t14-,16-,18+,19-,20+/m1/s1
InChIKey: UWTGBDCCWCEIBB-MMDFDTFJSA-N
DeepSMILES: OC/C=C/CC[C@@]CO))[C@H]C)C[C@@][C@@H]5CCC[C@@]C7)OC8=O)))C))))))))))))\CO
Scaffold Graph/Node/Bond level: O=C1OC2CCCC3CCCC13C2
Scaffold Graph/Node level: OC1OC2CCCC3CCCC31C2
Scaffold Graph level: CC1CC2CCCC3CCCC13C2
Functional groups: CO; C/C=C(/C)C; COC(=O)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: Sesquiterpenoids
Synonymous chemical names:
Portulic lactone, portulic lactone
External chemical identifiers:
CID:CID_21633001; ZINC:ZINC000146259609
Chemical structure download


Portulic lactone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.47
Log P RDKit 2.19
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.85
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Portulic lactone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.50379


Portulic lactone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.21
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 Yes