IMPPAT Phytochemical information: 
Maculosin
Maculosin
Summary

SMILES: O=C1N[C@@H](Cc2ccc(cc2)O)C(=O)N2[C@H]1CCC2
InChI: InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
InChIKey: LSGOTAXPWMCUCK-RYUDHWBXSA-N
DeepSMILES: O=CN[C@@H]Ccccccc6))O))))))C=O)N[C@H]6CCC5
Scaffold Graph/Node/Bond level: O=C1NC(Cc2ccccc2)C(=O)N2CCCC12
Scaffold Graph/Node level: OC1NC(CC2CCCCC2)C(O)N2CCCC12
Scaffold Graph level: CC1CC(CC2CCCCC2)C(C)C2CCCC12
Functional groups: CNC(=O)C; cO; CN(C)C(=O)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: Amino acids and Peptides
NP Classifier Superclass: Small peptides
NP Classifier Class: Dipeptides
Synonymous chemical names:
cyclol-pro-l-tyr
External chemical identifiers:
CID:CID_119404; ChEMBL:CHEMBL359788; ChEBI:CHEBI:6631; ZINC:ZINC000001629943; SureChEMBL:SCHEMBL12035399; MolPort-003-940-854
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Maculosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 260.29
Log P RDKit 0.42
Topological polar surface area (Å2) RDKit 69.64
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
Maculosin
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 0.81
Maculosin
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 -7.16
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 No
P-glycoprotein substrate SwissADME No