IMPPAT Phytochemical information: 
10-Epitrewiasine
10-Epitrewiasine
Summary

SMILES: COC1/C(=C/C=C/[C@H](OC)[C@]2(O)NC(=O)O[C@@H](C2)[C@H]([C@H]2[C@@]([C@H](CC(=O)N(c3cc1cc(OC)c3Cl)C)OC(=O)[C@@H](N(C(=O)C(C)C)C)C)(C)O2)C)/C
InChI: InChI=1S/C37H52ClN3O11/c1-19(2)33(43)40(7)22(5)34(44)51-28-17-29(42)41(8)24-15-23(16-25(47-9)30(24)38)31(49-11)20(3)13-12-14-27(48-10)37(46)18-26(50-35(45)39-37)21(4)32-36(28,6)52-32/h12-16,19,21-22,26-28,31-32,46H,17-18H2,1-11H3,(H,39,45)/b14-12+,20-13+/t21-,22+,26+,27+,28+,31?,32+,36+,37+/m1/s1
InChIKey: GNTFDQQBHGBGMN-SVKFYDQHSA-N
DeepSMILES: COC/C=C/C=C/[C@H]OC))[C@]O)NC=O)O[C@@H]C6)[C@H][C@H][C@@][C@H]CC=O)Nccc%21ccOC))c6Cl)))))))C))))OC=O)[C@@H]NC=O)CC)C)))C))C)))))C)O3)))C)))))))))))/C
Scaffold Graph/Node/Bond level: O=C1CCC2OC2CC2CC(CC=CC=CCc3cccc(c3)N1)NC(=O)O2
Scaffold Graph/Node level: OC1CCC2OC2CC2CC(CCCCCCC3CCCC(C3)N1)NC(O)O2
Scaffold Graph level: CC1CCC2CC2CC2CC(C)CC(CCCCCCC3CCCC(C1)C3)C2
Functional groups: COC; C/C(C)=C/C=C/C; C[C@@]1(O)CCOC(=O)N1; C[C@@]1(C)O[C@H]1C; cN(C)C(=O)C; cOC; cCl; COC(C)=O; CC(=O)N(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolactams
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Macrolides
NP Classifier Class: Ansa macrolides
Synonymous chemical names:
Epitrewiasine, 10-
External chemical identifiers:
CID:CID_44559316; ChEMBL:CHEMBL510998
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
10-Epitrewiasine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 750.29
Log P RDKit 4.32
Topological polar surface area (Å2) RDKit 165.7
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 52
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4
10-Epitrewiasine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.301428
10-Epitrewiasine
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -9.13
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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