IMPPAT Phytochemical information: 
Isorosmanol

Isorosmanol
Summary

SMILES: O[C@H]1[C@@H]2OC(=O)[C@]3([C@@H]1C(C)(C)CCC3)c1c2cc(C(C)C)c(c1O)O
InChI: InChI=1S/C20H26O5/c1-9(2)10-8-11-12(14(22)13(10)21)20-7-5-6-19(3,4)17(20)15(23)16(11)25-18(20)24/h8-9,15-17,21-23H,5-7H2,1-4H3/t15-,16+,17-,20-/m0/s1
InChIKey: UXVPWKDITRJELA-CLWJZODNSA-N
DeepSMILES: O[C@H][C@@H]OC=O)[C@][C@@H]6CC)C)CCC6)))))cc6ccCC)C))cc6O))O
Scaffold Graph/Node/Bond level: O=C1OC2CC3CCCCC13c1ccccc12
Scaffold Graph/Node level: OC1OC2CC3CCCCC31C1CCCCC21
Scaffold Graph level: CC1CC2CC3CCCCC13C1CCCCC21
Functional groups: CO; COC(=O)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: Diterpenoids
NP Classifier Class: Abietane diterpenoids
Synonymous chemical names:
isorosmanol, Isorosmanol
External chemical identifiers:
CID:CID_13820511; ChEMBL:CHEMBL494659; ChEBI:CHEBI:175403; ZINC:ZINC000031157838; SureChEMBL:SCHEMBL13294492
Chemical structure download


Isorosmanol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.42
Log P RDKit 3.26
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 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Isorosmanol
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 0.54


Isorosmanol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.99
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes