NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one (NP0145589)

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Record Information

Version

2.0

Created at

2022-09-02 00:49:14 UTC

Updated at

2022-09-02 00:49:14 UTC

NP-MRD ID

NP0145589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

Description

Luteolin-4'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. 5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one is found in Artemisia judaica, Campanula persicifolia, Centaurea deflexa, Chaenomeles sinensis, Genista corsica, Veronica stricta, Kummerowia striata, Lathyrus pratensis, Lawsonia inermis, Meehania urticifolia, Picris hieracioides, Punica granatum, Salix babylonica, Saussurea medusa, Serratula coronata, Tinospora crispa and Vicia subvillosa. 5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one was first documented in 2017 (PMID: 28840692). Luteolin-4'-O-beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 30989856) (PMID: 31646682) (PMID: 28222613) (PMID: 28620306).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006302D          

 32 35  0  0  0  0            999 V2000
   15.8139    2.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2370    2.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6755    2.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6889    0.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5410    0.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0440   -0.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5294    1.7159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2408    2.1354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9640    1.7263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9679    0.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2564    0.4830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2660   -0.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1028    0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1016   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8150   -0.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8132    0.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5274    0.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5307   -0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2485   -0.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9677   -0.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9642    0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2417    0.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2508   -1.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8136   -1.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3895    0.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6760    0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3933    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1048    0.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1026    1.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3832    2.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6746    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3776    2.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  2  0  0  0  0
 16 13  1  0  0  0  0
 17 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
  7  1  1  1  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  8  2  1  6  0  0  0
 19 23  2  0  0  0  0
  9  3  1  1  0  0  0
 15 24  1  0  0  0  0
 10  4  1  6  0  0  0
 13 25  1  0  0  0  0
 21 26  1  0  0  0  0
  6 12  1  0  0  0  0
 26 27  2  0  0  0  0
 13 14  2  0  0  0  0
 27 28  1  0  0  0  0
 11  5  1  0  0  0  0
 28 29  2  0  0  0  0
 14 15  1  0  0  0  0
 29 30  1  0  0  0  0
 15 18  2  0  0  0  0
 30 31  2  0  0  0  0
 31 26  1  0  0  0  0
  5  7  1  0  0  0  0
 30 32  1  0  0  0  0
 29  1  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    6.1981   -2.2473    1.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5590   -1.4181    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -1.4954    0.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865   -0.6202    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355   -0.6887    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2766   -1.6102    1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081   -1.6628    1.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8796   -0.7401    0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221   -0.8853    0.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827   -0.2301   -0.0549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0111    0.3317    1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0471    1.0757    0.4024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3893    2.1840    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3977    3.0061    0.9119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890    0.1136    0.2172 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1348    0.5506   -0.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908   -1.2262   -0.1447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5307   -2.0470    0.9741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2619   -1.1247   -0.8142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4357   -0.7073   -2.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297    0.2076   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656    1.1338   -1.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1394    0.2031   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593    0.3100   -0.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2559    0.4242   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8227    1.4065   -1.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1820    1.5433   -1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6899    2.5609   -2.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100    0.6974   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4696   -0.3105   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3177   -1.1417    0.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1068   -0.4451   -0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170   -2.2522    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -2.3617    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982   -2.4138    1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0292    0.5997   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6841    1.5068   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4947    2.8133    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6542    1.7333    2.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4196    3.1045   -0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945    0.0092    1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7784    1.1304   -0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2866   -1.7233   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.7229    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -2.1370   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -1.4551   -2.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    1.8005   -1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6682    0.9346   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1859    2.0805   -2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8454    2.3188   -3.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0858    0.7705   -1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2633   -1.8842    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 23  1  0
 23 21  2  0
 21 22  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 32  1  0
 32 30  2  0
 30 31  1  0
 30 29  1  0
 29 27  2  0
 27 28  1  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 10 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 12  1  0
 21  8  1  0
 24  4  1  0
 25 32  1  0
 14 40  1  0
 13 38  1  0
 13 39  1  0
 12 37  1  6
 10 36  1  6
  7 35  1  0
  6 34  1  0
 23 48  1  0
 22 47  1  0
  3 33  1  0
 31 52  1  0
 29 51  1  0
 28 50  1  0
 26 49  1  0
 19 45  1  6
 20 46  1  0
 17 43  1  6
 18 44  1  0
 15 41  1  1
 16 42  1  0
M  END


  Mrv1652309272006302D          

 32 35  0  0  0  0            999 V2000
   15.8139    2.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2370    2.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6755    2.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6889    0.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5410    0.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0440   -0.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5294    1.7159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2408    2.1354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9640    1.7263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9679    0.9027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2564    0.4830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2660   -0.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1028    0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1016   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8150   -0.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8132    0.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5274    0.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5307   -0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2485   -0.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9677   -0.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9642    0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2417    0.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2508   -1.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8136   -1.6036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3895    0.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6760    0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3933    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1048    0.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1026    1.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3832    2.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6746    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3776    2.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  2  0  0  0  0
 16 13  1  0  0  0  0
 17 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
  7  1  1  1  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  8  2  1  6  0  0  0
 19 23  2  0  0  0  0
  9  3  1  1  0  0  0
 15 24  1  0  0  0  0
 10  4  1  6  0  0  0
 13 25  1  0  0  0  0
 21 26  1  0  0  0  0
  6 12  1  0  0  0  0
 26 27  2  0  0  0  0
 13 14  2  0  0  0  0
 27 28  1  0  0  0  0
 11  5  1  0  0  0  0
 28 29  2  0  0  0  0
 14 15  1  0  0  0  0
 29 30  1  0  0  0  0
 15 18  2  0  0  0  0
 30 31  2  0  0  0  0
 31 26  1  0  0  0  0
  5  7  1  0  0  0  0
 30 32  1  0  0  0  0
 29  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(C=C2O)C2=CC(=O)C3=C(O)C=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-13-2-1-8(3-10(13)24)14-6-12(26)17-11(25)4-9(23)5-15(17)30-14/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
UHNXUSWGOJMEFO-QNDFHXLGSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.21497936672831

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.1350557186666665

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.15533747623271

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.577082531122513

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549038426

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
107.0392

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0      29.519   3.957   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      32.176   5.524   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.861   4.006   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.886   0.928   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.877   1.656   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.682  -1.142   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      30.855   3.203   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.183   3.986   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.533   3.223   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.540   1.685   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.212   0.902   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.230  -0.638   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.858   0.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.856  -0.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.188  -1.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.185   1.624   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.518   0.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.524  -0.691   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.864  -1.457   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.206  -0.680   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.200   0.872   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      22.851   1.647   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      22.868  -2.994   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.185  -2.993   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      17.527   1.623   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      25.529   1.645   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.867   0.873   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.196   1.644   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.192   3.183   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.849   3.947   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.526   3.171   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      26.838   5.484   0.000  0.00  0.00           O+0
CONECT    1    7   29                                                       
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   11    7                                                       
CONECT    6   12                                                            
CONECT    7    8    1    5                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   11    4                                                  
CONECT   11   10   12    5                                                  
CONECT   12   11    6                                                       
CONECT   13   16   25   14                                                  
CONECT   14   13   15                                                       
CONECT   15   24   14   18                                                  
CONECT   16   17   13                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   15                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   17   21                                                       
CONECT   23   19                                                            
CONECT   24   15                                                            
CONECT   25   13                                                            
CONECT   26   21   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30    1                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
5,7,3'-Trihydroxyflavone 4'-O-beta-D-glucopyranoside	ChEBI
5,7,3'-Trihydroxyflavone 4'-O-b-D-glucopyranoside	Generator
5,7,3'-Trihydroxyflavone 4'-O-β-D-glucopyranoside	Generator
Luteolin-4'-O-b-D-glucopyranoside	Generator
Luteolin-4'-O-β-D-glucopyranoside	Generator
Luteolin 4'-glucoside	PhytoBank
Luteolin 4’-glucoside	PhytoBank
2-[4-(beta-D-Glucopyranosyloxy)-3-hydroxyphenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one	PhytoBank
2-[4-(β-D-Glucopyranosyloxy)-3-hydroxyphenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one	PhytoBank
3',4',5,7-Tetrahydroxyflavone 4'-beta-D-glucoside	PhytoBank
3',4',5,7-Tetrahydroxyflavone 4'-β-D-glucoside	PhytoBank
3’,4’,5,7-Tetrahydroxyflavone 4’-β-D-glucoside	PhytoBank
4'-beta-D-Glucosylluteolin	PhytoBank
4'-β-D-Glucosylluteolin	PhytoBank
4’-β-D-Glucosylluteolin	PhytoBank
Luteolin 4'-O-glucoside	PhytoBank
Luteolin 4’-O-glucoside	PhytoBank
Luteolin 4'-O-beta-D-glucopyranoside	PhytoBank
Luteolin 4'-O-β-D-glucopyranoside	PhytoBank
Luteolin 4’-O-β-D-glucopyranoside	PhytoBank
Luteolin 4'-O-beta-D-glucoside	PhytoBank
Luteolin 4'-O-β-D-glucoside	PhytoBank
Luteolin 4’-O-β-D-glucoside	PhytoBank
Juncein	PhytoBank

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(C=C2O)C2=CC(=O)C3=C(O)C=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-13-2-1-8(3-10(13)24)14-6-12(26)17-11(25)4-9(23)5-15(17)30-14/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

InChI Key

UHNXUSWGOJMEFO-QNDFHXLGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia judaica	LOTUS Database	35616633
Campanula persicifolia	LOTUS Database	35616633
Centaurea deflexa	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Genista corsica	LOTUS Database	35616633
Hebe stricta	LOTUS Database	35616633
Kummerowia striata	LOTUS Database	35616633
Lathyrus pratensis	LOTUS Database	35616633
Lawsonia inermis	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Salix babylonica	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Serratula coronata	LOTUS Database	35616633
Tinospora crispa	LOTUS Database	35616633
Vicia subvillosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-4p-o-glycoside
Flavonoid o-glycoside
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:68986 )
monosaccharide derivative (CHEBI:68986 )
glycosyloxyflavone (CHEBI:68986 )
trihydroxyflavone (CHEBI:68986 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.56	ALOGPS
logP	0.14	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.04 m³·mol⁻¹	ChemAxon
Polarizability	43.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4477503

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319116

PDB ID

Not Available

ChEBI ID

68986

Good Scents ID

Not Available

References

General References

Liang X, Jiao YY, Wang WH, Li SF, Zhang LW: [Phenolic constituents from Wikstroemia chamaedaphne]. Zhongguo Zhong Yao Za Zhi. 2019 Mar;44(5):962-967. doi: 10.19540/j.cnki.cjcmm.2019.0017. [PubMed:30989856 ]
Wang LT, Sun ZH, Zhong ML, Wu HF, Zhang HJ, Zhu NL, Sun GB, Ye XX, Xu XD, Zhu YD, Yang JS: [Studies on chemical constituents of Clinopodium chinense]. Zhongguo Zhong Yao Za Zhi. 2017 Jul;42(13):2510-2517. doi: 10.19540/j.cnki.cjcmm.2017.0116. [PubMed:28840692 ]
Tian X, Guo S, Zhang S, Li P, Wang T, Ho CT, Pan MH, Bai N: Chemical characterization of main bioactive constituents in Paeonia ostii seed meal and GC-MS analysis of seed oil. J Food Biochem. 2020 Jan;44(1):e13088. doi: 10.1111/jfbc.13088. Epub 2019 Oct 23. [PubMed:31646682 ]
Dall'Acqua S, Peron G, Ferrari S, Gandin V, Bramucci M, Quassinti L, Martonfi P, Maggi F: Phytochemical investigations and antiproliferative secondary metabolites from Thymus alternans growing in Slovakia. Pharm Biol. 2017 Dec;55(1):1162-1170. doi: 10.1080/13880209.2017.1291689. [PubMed:28222613 ]
Iqbal K, Iqbal J, Staerk D, Kongstad KT: Characterization of Antileishmanial Compounds from Lawsonia inermis L. Leaves Using Semi-High Resolution Antileishmanial Profiling Combined with HPLC-HRMS-SPE-NMR. Front Pharmacol. 2017 May 31;8:337. doi: 10.3389/fphar.2017.00337. eCollection 2017. [PubMed:28620306 ]
LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one (NP0145589)

MOL for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D MOL for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D SDF for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D-SDF for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

PDB for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D PDB for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

SMILES for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

INCHI for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

Structure for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D Structure for NP0145589 (5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)