IMPPAT Phytochemical information: 
Lansioside A
Lansioside A
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CCC(=C)[C@@H]3CC[C@H]2C(=CC[C@H]([C@]2(C)CCC(=O)O)C(=C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
InChI: InChI=1S/C38H61NO8/c1-21(2)25-12-10-22(3)26(37(25,8)19-17-31(42)43)13-14-27-23(4)11-15-29-36(6,7)30(16-18-38(27,29)9)47-35-32(39-24(5)41)34(45)33(44)28(20-40)46-35/h10,25-30,32-35,40,44-45H,1,4,11-20H2,2-3,5-9H3,(H,39,41)(H,42,43)/t25-,26-,27-,28+,29-,30-,32+,33+,34+,35-,37-,38+/m0/s1
InChIKey: DPUBTAIUQYXFDA-RAWPCXBLSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]CC[C@][C@H]C6C)C))CCC=C)[C@@H]6CC[C@H]C=CC[C@H][C@]6C)CCC=O)O)))))C=C)C)))))C))))))))))C))))))[C@@H][C@H][C@@H]6O))O))NC=O)C
Scaffold Graph/Node/Bond level: C=C1CCC2CC(OC3CCCCO3)CCC2C1CCC1C=CCCC1
Scaffold Graph/Node level: CC1CCC2CC(OC3CCCCO3)CCC2C1CCC1CCCCC1
Scaffold Graph level: CC1CCC2CC(CC3CCCCC3)CCC2C1CCC1CCCCC1
Functional groups: CO; CC(=O)O; C=C(C)C; CO[C@@H](C)OC; CC(=O)NC; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Onocerane triterpenoids
Synonymous chemical names:
lansioside a
External chemical identifiers:
CID:CID_21634995; ChEBI:CHEBI:66545; ZINC:ZINC000096085625; SureChEMBL:SCHEMBL7147620
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lansioside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 659.91
Log P RDKit 5.53
Topological polar surface area (Å2) RDKit 145.55
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 30
Shape complexity RDKit 0.79
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Lansioside A
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 0.143794
Lansioside A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -6.30
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