IMPPAT Phytochemical information: 
[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,15,20-trimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(2-methylpropanoyl)amino]propanoate
[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,15,20-trimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(2-methylpropanoyl)amino]propanoate
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)Nc3cc1cc(c3Cl)OC)OC(=O)[C@@H](N(C(=O)C(C)C)C)C)(C)O2)C)/C
InChI: InChI=1S/C36H50ClN3O11/c1-18(2)32(42)40(7)21(5)33(43)50-27-16-28(41)38-23-14-22(15-24(46-8)29(23)37)30(48-10)19(3)12-11-13-26(47-9)36(45)17-25(49-34(44)39-36)20(4)31-35(27,6)51-31/h11-15,18,20-21,25-27,30-31,45H,16-17H2,1-10H3,(H,38,41)(H,39,44)/b13-11+,19-12+/t20-,21+,25+,26-,27+,30?,31+,35+,36+/m1/s1
InChIKey: PZDXJLHGUHZVRF-CLIJUWRQSA-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%21ccc6Cl))OC))))))))))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; cNC(=O)C; cCl; cOC; 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:
nortrewiasine
External chemical identifiers:
CID:CID_44559317; ChEMBL:CHEMBL447805
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,15,20-trimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(2-methylpropanoyl)amino]propanoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 736.26
Log P RDKit 4.29
Topological polar surface area (Å2) RDKit 174.49
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 51
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 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.61
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
[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,15,20-trimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(2-methylpropanoyl)amino]propanoate
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 0.269281
[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,15,20-trimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl(2-methylpropanoyl)amino]propanoate
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 -9.18
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