IMPPAT Phytochemical information: 
Juniperolide

Juniperolide
Summary

SMILES: O=C1C2=C[C@](O)(CC[C@@H]2[C@@]2([C@H]3[C@@H]1OC(=O)[C@@]3(C)CCC2)C)C(C)C
InChI: InChI=1S/C20H28O4/c1-11(2)20(23)9-6-13-12(10-20)14(21)15-16-18(13,3)7-5-8-19(16,4)17(22)24-15/h10-11,13,15-16,23H,5-9H2,1-4H3/t13-,15+,16+,18+,19-,20+/m0/s1
InChIKey: UGRRLQKVGXWATD-UYGWLRSGSA-N
DeepSMILES: O=CC=C[C@]O)CC[C@@H]6[C@@][C@H][C@@H]%10OC=O)[C@@]5C)CCC9))))))))C)))))CC)C
Scaffold Graph/Node/Bond level: O=C1OC2C(=O)C3=CCCCC3C3CCCC1C23
Scaffold Graph/Node level: OC1OC2C(O)C3CCCCC3C3CCCC1C32
Scaffold Graph level: CC1CC2C(C)C3CCCCC3C3CCCC1C23
Functional groups: CC=C(C)C(=O)C; CO; 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: Diterpenoids
NP Classifier Class: Abietane diterpenoids
Synonymous chemical names:
juniperolide
External chemical identifiers:
CID:CID_101552747; ZINC:ZINC000085887780
Chemical structure download


Juniperolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.44
Log P RDKit 3.03
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
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 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Juniperolide
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 0.75


Juniperolide
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.93
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes