IMPPAT Phytochemical information: 
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c(c3c2cccc3)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H28O13/c23-6-12-14(26)16(28)18(30)21(33-12)32-11-5-10(25)20(9-4-2-1-3-8(9)11)35-22-19(31)17(29)15(27)13(7-24)34-22/h1-5,12-19,21-31H,6-7H2/t12-,13-,14-,15-,16+,17+,18-,19-,21-,22+/m1/s1
InChIKey: MFKUFDGNYITGPN-WFRIJLMHSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6cccc6))))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc2c(OC3CCCCO3)ccc(OC3CCCCO3)c2c1
Scaffold Graph/Node level: C1CCC(OC2CCC(OC3CCCCO3)C3CCCCC23)OC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCCCC3)C3CCCCC23)CC1
Functional groups: CO; 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: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthalenes and derivatives
Synonymous chemical names:
lawsoniaside(1,2,4-trihydroxynaphthalene-1,4-di-β-d-glucopyranoside)
External chemical identifiers:
CID:CID_189451
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 500.45
Log P RDKit -3.1
Topological polar surface area (Å2) RDKit 218.99
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.192164
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-1-yl]oxyoxane-3,4,5-triol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.42
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No