IMPPAT Phytochemical information: 
(2S)-6,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
(2S)-6,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Summary

SMILES: CC(=CCc1c(O)c(O)c(c2c1O[C@@H](CC2=O)c1ccc(cc1)O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)C
InChI: InChI=1S/C32H40O15/c1-12(2)4-9-16-22(36)26(40)30(20-17(34)10-18(45-29(16)20)14-5-7-15(33)8-6-14)47-32-28(42)25(39)23(37)19(46-32)11-43-31-27(41)24(38)21(35)13(3)44-31/h4-8,13,18-19,21,23-25,27-28,31-33,35-42H,9-11H2,1-3H3/t13-,18-,19+,21-,23+,24+,25-,27+,28+,31+,32-/m0/s1
InChIKey: POYMCXRWXZAMNO-RXYNRAJXSA-N
DeepSMILES: CC=CCccO)cO)ccc6O[C@@H]CC6=O)))cccccc6))O)))))))))O[C@@H]O[C@H]CO[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))[C@H][C@@H][C@H]6O))O))O))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2cccc(OC3CCCC(COC4CCCCO4)O3)c21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCC(OC3CCCC(COC4CCCCO4)O3)C12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCC(CC3CCCC(CCC4CCCCC4)C3)C12
Functional groups: CC=C(C)C; cO; cOC; cC(=O)C; cO[C@@H](C)OC; CO[C@@H](C)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
nirurin [5,6,7,4'-tetrahydroxy-8-(3-methylbut-2-aryl) flavone -5-o-rutinoside]
External chemical identifiers:
CID:CID_21120611
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-6,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 664.66
Log P RDKit 0.05
Topological polar surface area (Å2) RDKit 245.29
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.34
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
(2S)-6,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
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 3
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 0.133683
(2S)-6,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.38
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME Yes