IMPPAT Phytochemical information: 
Periplogenin

Periplogenin
Summary

SMILES: O[C@H]1CC[C@]2([C@](C1)(O)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
InChI: InChI=1S/C23H34O5/c1-20-7-3-15(24)12-22(20,26)9-5-18-17(20)4-8-21(2)16(6-10-23(18,21)27)14-11-19(25)28-13-14/h11,15-18,24,26-27H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,20+,21+,22-,23-/m0/s1
InChIKey: QJPCKAJTLHDNCS-FBAXFMHRSA-N
DeepSMILES: O[C@H]CC[C@][C@]C6)O)CC[C@@H][C@@H]6CC[C@][C@]6O)CC[C@@H]5C=CC=O)OC5)))))))))C)))))))))C
Scaffold Graph/Node/Bond level: O=C1C=C(C2CCC3C2CCC2C4CCCCC4CCC23)CO1
Scaffold Graph/Node level: OC1CC(C2CCC3C2CCC2C4CCCCC4CCC23)CO1
Scaffold Graph level: CC1CCC(C2CCC3C2CCC2C4CCCCC4CCC23)C1
Functional groups: CO; CC1=CC(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cardenolides
Synonymous chemical names:
Periplogenin, periplogenin
External chemical identifiers:
CID:CID_10574; ChEMBL:CHEMBL460768; ZINC:ZINC000004023037; FDASRS:B6808P7IY9; SureChEMBL:SCHEMBL1483841; MolPort-002-508-311
Chemical structure download


Periplogenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 390.52
Log P RDKit 2.72
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 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 8
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.87
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Periplogenin
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 0.599472


Periplogenin
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 -7.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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