IMPPAT Phytochemical information: 
Cucumopine

Cucumopine
Summary

SMILES: OC(=O)CC[C@@]1(N[C@@H](Cc2c1nc[nH]2)C(=O)O)C(=O)O
InChI: InChI=1S/C11H13N3O6/c15-7(16)1-2-11(10(19)20)8-5(12-4-13-8)3-6(14-11)9(17)18/h4,6,14H,1-3H2,(H,12,13)(H,15,16)(H,17,18)(H,19,20)/t6-,11-/m0/s1
InChIKey: XGCZNSAJOHDWQS-KGFZYKRKSA-N
DeepSMILES: OC=O)CC[C@@]N[C@@H]Ccc6nc[nH]5))))))C=O)O))))C=O)O
Scaffold Graph/Node/Bond level: c1nc2c([nH]1)CCNC2
Scaffold Graph/Node level: C1CC2NCNC2CN1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CC(=O)O; CNC; cnc; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Histidine alkaloids
NP Classifier Class: Imidazole alkaloids
Synonymous chemical names:
mikimopine, Mikimopine
External chemical identifiers:
CID:CID_441561; ChEBI:CHEBI:3937; MolPort-046-196-580
Chemical structure download


Cucumopine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 283.24
Log P RDKit -0.85
Topological polar surface area (Å2) RDKit 152.61
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Cucumopine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.46826


Cucumopine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -10.61
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No