IMPPAT Phytochemical information: 
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl]oxy]oxan-2-yl]methyl hexadecanoate
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl]oxy]oxan-2-yl]methyl hexadecanoate
Summary

SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)C=C3[C@@H]4[C@@H]2c2cc5OCOc5cc2CN4CC3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C38H57NO10/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-31(41)45-22-30-34(42)35(43)36(44)38(48-30)49-37-27(40)18-24-16-17-39-21-25-19-28-29(47-23-46-28)20-26(25)32(37)33(24)39/h18-20,27,30,32-38,40,42-44H,2-17,21-23H2,1H3/t27-,30+,32-,33+,34+,35-,36+,37+,38-/m0/s1
InChIKey: ALECKIMNHVMLRG-YQNLORQQSA-N
DeepSMILES: CCCCCCCCCCCCCCCC=O)OC[C@H]O[C@@H]O[C@@H][C@@H]O)C=C[C@@H][C@@H]6cccOCOc5cc9CN%13CC%16))))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=C2CCN3Cc4cc5c(cc4C(C(OC4CCCCO4)C1)C23)OCO5
Scaffold Graph/Node level: C1CCC(OC2CCC3CCN4CC5CC6OCOC6CC5C2C34)OC1
Scaffold Graph level: C1CCC(CC2CCC3CCC4CC5CC6CCCC6CC5C2C34)CC1
Functional groups: c1cOCO1; CN(C)C; CO; COC(C)=O; CO[C@@H](C)OC; CC(=CC)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Lycorine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
lycoriside, lycoriside (lycorine-1-o-(6'-o-palmitoyl-β-d-glucopyranoside), Lycoriside
External chemical identifiers:
CID:CID_102074928
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl]oxy]oxan-2-yl]methyl hexadecanoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 687.87
Log P RDKit 4.61
Topological polar surface area (Å2) RDKit 147.38
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
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 9
Number of sp3 hybridized carbon atoms RDKit 29
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 19
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
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 6
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl]oxy]oxan-2-yl]methyl hexadecanoate
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 0.0975325
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl]oxy]oxan-2-yl]methyl hexadecanoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly 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 -6.42
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 Yes
P-glycoprotein substrate SwissADME Yes