NP-MRD: Showing NP-Card for Wogonin 7-glucuronide (NP0052498)

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Record Information

Version

2.0

Created at

2022-04-27 23:31:12 UTC

Updated at

2022-04-27 23:31:12 UTC

NP-MRD ID

NP0052498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wogonin 7-glucuronide

Description

Wogonin 7-O-beta-D-glucuronide, also known as oroxindin, belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Thus, wogonin 7-O-beta-D-glucuronide is considered to be a flavonoid. Wogonin 7-glucuronide is found in Glycyrrhiza glabra , Scutellaria alpina, Scutellaria altissima, Scutellaria baicalensis , Scutellaria discolor, Scutellaria galericulata , Scutellaria indica and Scutellaria orientalis. Wogonin 7-glucuronide was first documented in 2012 (PMID: 22574444). Based on a literature review a small amount of articles have been published on wogonin 7-O-beta-D-glucuronide (PMID: 28623444) (PMID: 28027008).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201312D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  6  0  0  0
 24 32  1  1  0  0  0
 23 33  1  6  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -0.0432   -0.4797    1.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959    0.4651    0.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161    0.0336   -0.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -0.3214   -1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7303   -0.3034   -1.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403    0.0699   -0.7484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1695   -1.1307   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1983   -0.8687    0.7030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3632   -2.0398    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6643   -3.0601    1.4797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3423   -1.9973    2.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4319   -0.5928   -0.1341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3326    0.1403    0.6262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689    0.0980   -1.4323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0384   -0.7854   -2.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944    0.8967   -1.3027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0613    1.9662   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1322   -0.7383   -3.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -0.7975   -3.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9452   -1.2221   -4.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -0.4256   -2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7491   -0.4447   -2.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594   -0.8116   -3.4820 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5439   -0.0451   -1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.3645   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8295    0.7838    1.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923    1.1845    2.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741    1.5957    3.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551    1.6087    3.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9141    1.2204    2.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1968    0.8046    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990    0.3612   -0.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025   -0.0076   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672    0.0602    2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9392   -0.7102    1.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -1.3632    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096    0.6163    0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    0.0088    1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3352   -1.9891    2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9040   -1.5672   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6751    0.8749    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8790    0.8284   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4687   -0.4011   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536    1.2782   -2.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870    2.5606   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -1.0294   -3.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7944   -1.3561   -4.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6194   -0.0721   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037    1.1642    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3712    1.9063    4.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7695    1.9357    4.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0049    1.2318    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7180    0.5017    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 33  2  0
 33 32  1  0
 32 25  1  0
 25 24  2  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 18  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
  4  3  1  0
 16  6  1  0
 31 26  1  0
 21 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 24 48  1  0
 20 47  1  0
 18 46  1  0
  6 37  1  1
  8 38  1  1
 12 40  1  6
 13 41  1  0
 14 42  1  6
 15 43  1  0
 16 44  1  6
 17 45  1  0
 11 39  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  1  0
 31 53  1  0
M  END


  Mrv1652304282201312D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  6  0  0  0
 24 32  1  1  0  0  0
 23 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(=CC(=O)C2=C(O)C=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1

> <INCHI_KEY>
LNOHXHDWGCMVCO-NTKSAMNMSA-N

> <FORMULA>
C22H20O11

> <MOLECULAR_WEIGHT>
460.391

> <EXACT_MASS>
460.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.877634993670696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
0.9047896343333338

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.836534449702756

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7056924042498642

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868279933102004

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
109.40799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oroxindin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    3                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25                                                            
CONECT   32   24                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-8-methoxyflavone 7-O-beta-D-glucuronide	ChEBI
5,7-Dihydroxy-8-methoxyflavone 7-O-b-D-glucuronide	Generator
5,7-Dihydroxy-8-methoxyflavone 7-O-β-D-glucuronide	Generator
Wogonin 7-O-b-D-glucuronide	Generator
Wogonin 7-O-β-D-glucuronide	Generator
Oroxindin	MeSH

Chemical Formula

C₂₂H₂₀O₁₁

Average Mass

460.3910 Da

Monoisotopic Mass

460.10056 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxane-2-carboxylic acid

Traditional Name

oroxindin

CAS Registry Number

Not Available

SMILES

COC1=C2OC(=CC(=O)C2=C(O)C=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1

InChI Key

LNOHXHDWGCMVCO-NTKSAMNMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Glycyrrhiza glabra	Plant	KNApSAcK
Scutellaria alpina	LOTUS Database	35616633
Scutellaria altissima	LOTUS Database	35616633
Scutellaria baicalensis	Plant	KNApSAcK
Scutellaria discolor	LOTUS Database	35616633
Scutellaria galericulata	Plant	KNApSAcK
Scutellaria indica	LOTUS Database	35616633
Scutellaria orientalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Pyranone
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Acetal
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:61282 )
beta-D-glucosiduronic acid (CHEBI:61282 )
monomethoxyflavone (CHEBI:61282 )
glycosyloxyflavone (CHEBI:61282 )
monohydroxyflavone (CHEBI:61282 )

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	1.16	ALOGPS
logP	0.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.41 m³·mol⁻¹	ChemAxon
Polarizability	43.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

2341950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3084961

PDB ID

Not Available

ChEBI ID

61282

Good Scents ID

Not Available

References

General References

Paudel MK, Sakamoto S, Tanaka H, Morimoto S: An overview and comparison of a recombinant antigen-binding fragment and an antigen-binding fragment from a monoclonal antibody against wogonin glucuronide. J Nat Med. 2017 Oct;71(4):703-710. doi: 10.1007/s11418-017-1100-y. Epub 2017 Jun 16. [PubMed:28623444 ]
Paudel MK, Sakamoto S, Huy LV, Tanaka H, Miyamoto T, Takano A, Morimoto S: Development of an immunoassay using an anti-wogonin glucuronide monoclonal antibody. J Immunoassay Immunochem. 2017;38(5):457-470. doi: 10.1080/15321819.2016.1273236. Epub 2016 Dec 27. [PubMed:28027008 ]
Kuroda M, Iwabuchi K, Mimaki Y: Chemical constituents of the aerial parts of Scutellaria lateriflora and their alpha-glucosidase inhibitory activities. Nat Prod Commun. 2012 Apr;7(4):471-4. [PubMed:22574444 ]

Showing NP-Card for Wogonin 7-glucuronide (NP0052498)

MOL for NP0052498 (Wogonin 7-glucuronide)

3D MOL for NP0052498 (Wogonin 7-glucuronide)

3D SDF for NP0052498 (Wogonin 7-glucuronide)

3D-SDF for NP0052498 (Wogonin 7-glucuronide)

PDB for NP0052498 (Wogonin 7-glucuronide)

3D PDB for NP0052498 (Wogonin 7-glucuronide)

SMILES for NP0052498 (Wogonin 7-glucuronide)

INCHI for NP0052498 (Wogonin 7-glucuronide)

Structure for NP0052498 (Wogonin 7-glucuronide)

3D Structure for NP0052498 (Wogonin 7-glucuronide)