IMPPAT Phytochemical information: 
Zizyphine A
Zizyphine A
Summary

SMILES: CC[C@@H]([C@@H](C(=O)N1CC[C@H]2[C@H]1C(=O)N1CCC[C@H]1C(=O)N/C=C\c1ccc(O2)cc1OC)NC(=O)[C@H]([C@H](CC)C)N(C)C)C
InChI: InChI=1S/C33H49N5O6/c1-8-20(3)27(35-31(40)28(36(5)6)21(4)9-2)32(41)38-18-15-25-29(38)33(42)37-17-10-11-24(37)30(39)34-16-14-22-12-13-23(44-25)19-26(22)43-7/h12-14,16,19-21,24-25,27-29H,8-11,15,17-18H2,1-7H3,(H,34,39)(H,35,40)/b16-14-/t20-,21-,24-,25-,27-,28-,29-/m0/s1
InChIKey: NXCUAFMNFVTKHA-YEEQOOFQSA-N
DeepSMILES: CC[C@@H][C@@H]C=O)NCC[C@H][C@H]5C=O)NCCC[C@H]5C=O)N/C=C\ccccO%17)cc6OC))))))))))))))))))))))))NC=O)[C@H][C@H]CC))C))NC)C))))))C
Scaffold Graph/Node/Bond level: O=C1NC=Cc2ccc(cc2)OC2CCNC2C(=O)N2CCCC12
Scaffold Graph/Node level: OC1NCCC2CCC(CC2)OC2CCNC2C(O)N2CCCC12
Scaffold Graph level: CC1CCCC2CCC(CC2)CC2CCCC2C(C)C2CCCC12
Functional groups: CNC(C)=O; CN(C(C)=O)C; CN(C)C; CN(C)C(=O)C; c/C=C\NC(=O)C; cOC
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|Amino acids and Peptides
NP Classifier Superclass: Peptide alkaloids
NP Classifier Class: Ansa peptide alkaloids
Synonymous chemical names:
Zizyphine A, zizyphine a
External chemical identifiers:
CID:CID_6324833; ChEBI:CHEBI:10121; ZINC:ZINC000095630242
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Zizyphine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 611.78
Log P RDKit 2.64
Topological polar surface area (Å2) RDKit 120.52
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
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 5
Zizyphine A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.440656
Zizyphine A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.21
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 No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes