IMPPAT Phytochemical information: 
Asparagamine A
Asparagamine A
Summary

SMILES: CC/C=C/[C@]12[C@@H]3CC4N1CC[C@H]2C1(O3)C4[C@@H](/C(=C\2/OC(=O)C(=C2OC)C)/O1)C
InChI: InChI=1S/C22H27NO5/c1-5-6-8-21-14-7-9-23(21)13-10-15(21)27-22(14)16(13)11(2)18(28-22)19-17(25-4)12(3)20(24)26-19/h6,8,11,13-16H,5,7,9-10H2,1-4H3/b8-6+,19-18-/t11-,13?,14+,15-,16?,21-,22?/m0/s1
InChIKey: XNUWGEPKIOWLHQ-ZYRMMYEKSA-N
DeepSMILES: CC/C=C/[C@][C@@H]CCN5CC[C@H]8CO9)C7[C@@H]/C=C/OC=O)C=C/5OC)))C)))))/O5))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=C2CC3C4CC5OC3(O2)C2CCN4C52)O1
Scaffold Graph/Node level: OC1CCC(C2CC3C4CC5OC3(O2)C2CCN4C52)O1
Scaffold Graph level: CC1CCC(C2CC3C4CC5CC3(C2)C2CCC4C52)C1
Functional groups: C/C=C/C; CN(C)C; COC1=C(C)C(=O)O/C1=C1/CCC(C)(OC)O1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Stemona alkaloids
Synonymous chemical names:
asparagamine a
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Asparagamine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 385.46
Log P RDKit 2.87
Topological polar surface area (Å2) RDKit 57.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Asparagamine A
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 0.55
Asparagamine A
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.95
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