IMPPAT Phytochemical information: 
Dihydro-beta-cyclopyrethrosin

Dihydro-beta-cyclopyrethrosin
Summary

SMILES: CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)[C@@H]2C)C[C@@]2([C@@H]1C(=C)CC[C@H]2O)C
InChI: InChI=1S/C17H24O5/c1-8-5-6-12(19)17(4)7-11-13(9(2)16(20)22-11)15(14(8)17)21-10(3)18/h9,11-15,19H,1,5-7H2,2-4H3/t9-,11+,12-,13-,14-,15+,17+/m1/s1
InChIKey: QBVSABVMVPCSEJ-JWKUIGNISA-N
DeepSMILES: CC=O)O[C@H][C@H][C@@H]OC=O)[C@@H]5C))))C[C@@][C@@H]6C=C)CC[C@H]6O))))))C
Scaffold Graph/Node/Bond level: C=C1CCCC2CC3OC(=O)CC3CC12
Scaffold Graph/Node level: CC1CCCC2CC3OC(O)CC3CC12
Scaffold Graph level: CC1CC2CC3CCCC(C)C3CC2C1
Functional groups: CC(=O)OC; COC(=O)C; C=C(C)C; CO
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
NP Classifier Class: Eudesmane sesquiterpenoids
Synonymous chemical names:
dihydro-beta-cyclopyrethrosin
External chemical identifiers:
CID:CID_21592279; ChEMBL:CHEMBL463059; ZINC:ZINC000040866382
Chemical structure download


Dihydro-beta-cyclopyrethrosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 308.37
Log P RDKit 1.83
Topological polar surface area (Å2) RDKit 72.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 2
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


Dihydro-beta-cyclopyrethrosin
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.590839


Dihydro-beta-cyclopyrethrosin
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 -6.94
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No