IMPPAT Phytochemical information: 
(1R,4R,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol
(1R,4R,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol
Summary

SMILES: OCC1=CC[N@+]2([C@H]1[C@H](O)CC2)[O-].OCC1=CC[N@+]2([C@H]1[C@H](O)CC2)[O-]
InChI: InChI=1S/2C8H13NO3/c2*10-5-6-1-3-9(12)4-2-7(11)8(6)9/h2*1,7-8,10-11H,2-5H2/t2*7-,8-,9+/m11/s1
InChIKey: HQCZBENCWMGBQS-DJBHWWRKSA-N
DeepSMILES: OCC=CC[N@+][C@H]5[C@H]O)CC5))))[O-].OCC=CC[N@+][C@H]5[C@H]O)CC5))))[O-]
Functional groups: CO; CC=C(C)C; C[N@@+]([O-])(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
Synonymous chemical names:
isatinecine
External chemical identifiers:
CID:CID_3038509
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,4R,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.39
Log P RDKit -1.27
Topological polar surface area (Å2) RDKit 127.04
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
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 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(1R,4R,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-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 Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.28
(1R,4R,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-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 Low
Log Kp (Skin permeation, cm/s) SwissADME -10.90
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 Yes