IMPPAT Phytochemical information: 
Atropine oxide

Atropine oxide
Summary

SMILES: OCC(c1ccccc1)C(=O)OC1C[C@@H]2CC[C@H](C1)[N+]2([O-])C
InChI: InChI=1S/C17H23NO4/c1-18(21)13-7-8-14(18)10-15(9-13)22-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16?,18?
InChIKey: HGWPFSBHDACWNL-GFBLOWMDSA-N
DeepSMILES: OCCcccccc6))))))C=O)OCC[C@@H]CC[C@H]C7)[N+]5[O-])C
Scaffold Graph/Node/Bond level: O=C(Cc1ccccc1)OC1CC2CCC(C1)[NH2+]2
Scaffold Graph/Node level: OC(CC1CCCCC1)OC1CC2CCC(C1)N2
Scaffold Graph level: CC(CC1CCCCC1)CC1CC2CCC(C2)C1
Functional groups: CO; COC(C)=O; C[N+]([O-])(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Tropane alkaloids
Synonymous chemical names:
hyoscyamine-n-oxide, hyoscyamine n-oxide
External chemical identifiers:
CID:CID_3000668
Chemical structure download


Atropine oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 305.37
Log P RDKit 1.94
Topological polar surface area (Å2) RDKit 69.59
Number of hydrogen bond acceptors RDKit 4
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 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Atropine oxide
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 0.52


Atropine oxide
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 -7.20
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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