IMPPAT Phytochemical information: 
15R-PGA2 methyl ester, 15-acetate

15R-PGA2 methyl ester, 15-acetate
Summary

SMILES: CCCCC[C@@H](OC(=O)C)/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)OC
InChI: InChI=1S/C23H34O5/c1-4-5-8-11-20(28-18(2)24)16-14-19-15-17-22(25)21(19)12-9-6-7-10-13-23(26)27-3/h6,9,14-17,19-21H,4-5,7-8,10-13H2,1-3H3/b9-6-,16-14+/t19-,20+,21+/m0/s1
InChIKey: KURMKPDMINCWHJ-QPBHISEGSA-N
DeepSMILES: CCCCC[C@@H]OC=O)C)))/C=C/[C@H]C=CC=O)[C@@H]5C/C=C\CCCC=O)OC
Scaffold Graph/Node/Bond level: O=C1C=CCC1
Scaffold Graph/Node level: OC1CCCC1
Scaffold Graph level: CC1CCCC1
Functional groups: CC(=O)OC; C/C=C/C; O=C1C=CCC1; C/C=C\C; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Eicosanoids
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Eicosanoids
NP Classifier Class: Isoprostanes|Prostaglandins
Synonymous chemical names:
prostaglandin
External chemical identifiers:
CID:CID_42607302; ChEBI:CHEBI:168746; ZINC:ZINC000102185384
Chemical structure download


15R-PGA2 methyl ester, 15-acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 390.52
Log P RDKit 4.72
Topological polar surface area (Å2) RDKit 69.67
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.61
Number of rotatable bonds RDKit 15
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1


15R-PGA2 methyl ester, 15-acetate
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 Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.258588


15R-PGA2 methyl ester, 15-acetate
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 -5.48
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes