IMPPAT Phytochemical information: 
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13R,16S,17S,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-12-oxo-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13R,16S,17S,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-12-oxo-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Summary

SMILES: CO[C@H]1C[C@@]2(O)[C@H]3[C@H]([C@@H]1C[C@H]3[C@@]13[C@H]4[C@]2(O)[C@@H](OC)[C@@H]1[C@](C(=O)N4)(CC[C@@H]3OC)COC(=O)c1ccccc1N1C(=O)C[C@@H](C1=O)C)OC
InChI: InChI=1S/C35H44N2O11/c1-16-12-23(38)37(28(16)39)20-9-7-6-8-17(20)29(40)48-15-32-11-10-22(45-3)34-19-13-18-21(44-2)14-33(42,24(19)25(18)46-4)35(43,27(47-5)26(32)34)30(34)36-31(32)41/h6-9,16,18-19,21-22,24-27,30,42-43H,10-15H2,1-5H3,(H,36,41)/t16-,18+,19+,21-,22-,24+,25-,26+,27-,30-,32-,33+,34-,35+/m0/s1
InChIKey: WSFIYJSHRVUTRA-MTGFEDCLSA-N
DeepSMILES: CO[C@H]C[C@@]O)[C@H][C@H][C@@H]6C[C@H]5[C@@][C@H][C@]9O)[C@@H]OC))[C@@H]5[C@]C=O)N7))CC[C@@H]9OC)))))COC=O)cccccc6NC=O)C[C@@H]C5=O))C)))))))))))))))))))))))OC
Scaffold Graph/Node/Bond level: O=C(OCC12CCCC34C5CC6CCC(C5C6)C(CC13)C4NC2=O)c1ccccc1N1C(=O)CCC1=O
Scaffold Graph/Node level: OC(OCC12CCCC34C5CC6CCC(C5C6)C(CC13)C4NC2O)C1CCCCC1N1C(O)CCC1O
Scaffold Graph level: CC(CCC12CCCC34C5CC6CCC(C5C6)C(CC13)C4CC2C)C1CCCCC1C1C(C)CCC1C
Functional groups: COC; CO; cN1C(=O)CCC1=O; CNC(=O)C; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
zaliline
External chemical identifiers:
CID:CID_101631702; ZINC:ZINC000084923897
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13R,16S,17S,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-12-oxo-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 668.74
Log P RDKit 0.83
Topological polar surface area (Å2) RDKit 170.16
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13R,16S,17S,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-12-oxo-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.26
[(1S,2R,3R,4S,5R,6S,8R,9S,10S,13R,16S,17S,18S)-8,9-dihydroxy-4,6,16,18-tetramethoxy-12-oxo-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME 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 -10.67
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