IMPPAT Phytochemical information: 
Lithospermoside
Lithospermoside
Summary

SMILES: N#C/C=C\1/C=C[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
InChI: InChI=1S/C14H19NO8/c15-4-3-6-1-2-7(17)9(18)13(6)23-14-12(21)11(20)10(19)8(5-16)22-14/h1-3,7-14,16-21H,5H2/b6-3-/t7-,8-,9+,10-,11+,12-,13+,14+/m1/s1
InChIKey: WIIDBJNWXCWLKF-VVAXPEBGSA-N
DeepSMILES: N#C/C=C/C=C[C@H][C@@H][C@H]/6O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))O))O
Scaffold Graph/Node/Bond level: C=C1C=CCCC1OC1CCCCO1
Scaffold Graph/Node level: CC1CCCCC1OC1CCCCO1
Scaffold Graph level: CC1CCCCC1CC1CCCCC1
Functional groups: CC=C/C(=C/C#N)C; CO[C@@H](C)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Amino acids and Peptides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Small peptides
NP Classifier Class: Aminoacids
Synonymous chemical names:
Lithospermoside
External chemical identifiers:
CID:CID_10065132; ChEMBL:CHEMBL1817899; ZINC:ZINC000056874786; SureChEMBL:SCHEMBL21034847; Molport-027-720-886
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lithospermoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 329.31
Log P RDKit -3.09
Topological polar surface area (Å2) RDKit 163.63
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.57
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Lithospermoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
Lithospermoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.64
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