IMPPAT Phytochemical information: 
Stephanaberrine

Stephanaberrine
Summary

SMILES: CN1CCC23C41C[C@@H](O[C@]4(O)C(=O)CC2)c1c3cc2c(c1)OCO2
InChI: InChI=1S/C18H19NO5/c1-19-5-4-16-3-2-15(20)18(21)17(16,19)8-14(24-18)10-6-12-13(7-11(10)16)23-9-22-12/h6-7,14,21H,2-5,8-9H2,1H3/t14-,16?,17?,18-/m1/s1
InChIKey: CRHLDFQHFBGPOT-AGERRDQYSA-N
DeepSMILES: CNCCCC5C[C@@H]O[C@]5O)C=O)CC9)))))cc6cccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1CCC23CCNC24CC(OC14)c1cc2c(cc13)OCO2
Scaffold Graph/Node level: OC1CCC23CCNC24CC(OC14)C1CC2OCOC2CC13
Scaffold Graph level: CC1CCC23CCCC24CC(CC14)C1CC2CCCC2CC13
Functional groups: CN(C)C; CC(=O)[C@](O)(C)OC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Hasubanan alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
stephanaberrine
External chemical identifiers:
CID:CID_184518
Chemical structure download


Stephanaberrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 329.35
Log P RDKit 1.25
Topological polar surface area (Å2) RDKit 68.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.61
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Stephanaberrine
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 0.77


Stephanaberrine
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 -7.87
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No