IMPPAT Phytochemical information: 
(1R,4S,7R)-1-(2-hydroxyethyl)-7-(hydroxymethyl)-2-oxabicyclo[2.2.1]heptan-7-ol
(1R,4S,7R)-1-(2-hydroxyethyl)-7-(hydroxymethyl)-2-oxabicyclo[2.2.1]heptan-7-ol
Summary

SMILES: OCC[C@@]12CC[C@H]([C@@]2(O)CO)CO1
InChI: InChI=1S/C9H16O4/c10-4-3-8-2-1-7(5-13-8)9(8,12)6-11/h7,10-12H,1-6H2/t7-,8+,9-/m0/s1
InChIKey: ZTVGFVPGILCAPR-YIZRAAEISA-N
DeepSMILES: OCC[C@]CC[C@H][C@@]5O)CO)))CO6
Scaffold Graph/Node/Bond level: C1CC2CC1CO2
Scaffold Graph/Node level: C1CC2CC1CO2
Scaffold Graph level: C1CC2CCC1C2
Functional groups: CO; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxanes
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
cyclocerberidol
External chemical identifiers:
CID:CID_14466835; ZINC:ZINC000013414861
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,4S,7R)-1-(2-hydroxyethyl)-7-(hydroxymethyl)-2-oxabicyclo[2.2.1]heptan-7-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 188.22
Log P RDKit -0.73
Topological polar surface area (Å2) RDKit 69.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 1
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2
(1R,4S,7R)-1-(2-hydroxyethyl)-7-(hydroxymethyl)-2-oxabicyclo[2.2.1]heptan-7-ol
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 1
Ghose rule RDKit Failed
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 0.55
(1R,4S,7R)-1-(2-hydroxyethyl)-7-(hydroxymethyl)-2-oxabicyclo[2.2.1]heptan-7-ol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.39
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