IMPPAT Phytochemical information: 
cyclo[DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe]
cyclo[DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe]
Summary

SMILES: CC(C1OC(=O)C(Cc2ccccc2)N(C)C(=O)C(OC(=O)C(N(C(=O)C(OC(=O)C(N(C1=O)C)Cc1ccccc1)C(C)C)C)Cc1ccccc1)C(C)C)C
InChI: InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3
InChIKey: GYSCAQFHASJXRS-UHFFFAOYSA-N
DeepSMILES: CCCOC=O)CCcccccc6)))))))NC)C=O)COC=O)CNC=O)COC=O)CNC%18=O))C))Ccccccc6))))))))))CC)C))))C))Ccccccc6))))))))))CC)C)))))))))C
Scaffold Graph/Node/Bond level: O=C1COC(=O)C(Cc2ccccc2)NC(=O)COC(=O)C(Cc2ccccc2)NC(=O)COC(=O)C(Cc2ccccc2)N1
Scaffold Graph/Node level: OC1COC(O)C(CC2CCCCC2)NC(O)COC(O)C(CC2CCCCC2)NC(O)COC(O)C(CC2CCCCC2)N1
Scaffold Graph level: CC1CCC(C)C(CC2CCCCC2)CC(C)CCC(C)C(CC2CCCCC2)CC(C)CCC(C)C(CC2CCCCC2)C1
Functional groups: CC(=O)N(C)C; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Peptidomimetics
ClassyFire Subclass: Depsipeptides
NP Classifier Biosynthetic pathway: Amino acids and Peptides|Polyketides
NP Classifier Superclass: Oligopeptides
NP Classifier Class: Cyclic peptides|Depsipeptides
Synonymous chemical names:
beauvericin
External chemical identifiers:
CID:CID_105014; ChEMBL:CHEMBL1977672; SureChEMBL:SCHEMBL6452789
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
cyclo[DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe]
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 783.96
Log P RDKit 4.91
Topological polar surface area (Å2) RDKit 139.83
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 45
Number of heavy atoms RDKit 57
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
cyclo[DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe]
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.218887
cyclo[DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe-DL-OVal-DL-N(Me)Phe]
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.10
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 Yes