IMPPAT Phytochemical information: 
Chaetoglobosin U
Chaetoglobosin U
Summary

SMILES: C[C@H]1C/C=C/[C@H]2[C@@H]3O[C@]3(C)[C@H]([C@@H]3[C@@]2(C(=O)C[C@@H]2[C@@H]1C(=C(C2=O)O)C)C(=O)N[C@H]3Cc1c[nH]c2c1cccc2)C
InChI: InChI=1S/C32H36N2O5/c1-15-8-7-10-21-29-31(4,39-29)17(3)26-23(12-18-14-33-22-11-6-5-9-19(18)22)34-30(38)32(21,26)24(35)13-20-25(15)16(2)27(36)28(20)37/h5-7,9-11,14-15,17,20-21,23,25-26,29,33,36H,8,12-13H2,1-4H3,(H,34,38)/b10-7+/t15-,17-,20+,21-,23-,25-,26-,29-,31+,32+/m0/s1
InChIKey: MRENMDHAGXAXRK-QFHPAQOTSA-N
DeepSMILES: C[C@H]C/C=C/[C@H][C@@H]O[C@]3C)[C@H][C@@H][C@@]7C=O)C[C@@H][C@@H]%15C=CC5=O))O))C))))))C=O)N[C@H]5Ccc[nH]cc5cccc6)))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2CCC=CC3C4OC4CC4C(Cc5c[nH]c6ccccc56)NC(=O)C34C(=O)CC12
Scaffold Graph/Node level: OC1CCC2CCCCC3C4OC4CC4C(CC5CNC6CCCCC56)NC(O)C43C(O)CC12
Scaffold Graph level: CC1CCC2CCCCC3C4CC4CC4C(CC5CCC6CCCCC65)CC(C)C43C(C)CC12
Functional groups: C/C=C/C; C[C@]1(C)O[C@H]1C; CC(=O)C; CC1=C(O)C(=O)CC1; CNC(=O)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Cytochalasans
ClassyFire Subclass: Chaetoglobosins
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Cytochalasan alkaloids
Synonymous chemical names:
chaetoglobosin
External chemical identifiers:
CID:CID_11570022; ChEMBL:CHEMBL448756; ChEBI:CHEBI:68733; ZINC:ZINC000100091823
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Chaetoglobosin U
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 528.65
Log P RDKit 4.44
Topological polar surface area (Å2) RDKit 111.79
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Chaetoglobosin U
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 0.30324
Chaetoglobosin U
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
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 3
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