NP-MRD: Showing NP-Card for (2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0249938)

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Record Information

Version

2.0

Created at

2022-09-07 12:38:14 UTC

Updated at

2022-09-07 12:38:15 UTC

NP-MRD ID

NP0249938

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

Kaempferol 3-O-glucuronide belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Kaempferol 3-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Kaempferol 3-O-glucuronide may be a unique S. (2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Diospyros kaki, Diplusodon uninervius and Pteris vittata. Cerevisiae (yeast) metabolite.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241223232D          

 33 36  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  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    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
   -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 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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579   -1.6500    0.0000 O   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
    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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    3.3980   -3.0284    1.7237 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398   -2.2685    0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3199   -2.6301    0.5853 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610   -0.9953    0.4628 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1942   -0.8003    0.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4909    0.1941    0.2272 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5033   -0.3996   -0.5962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7813   -0.6035   -0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177    0.2296   -0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7046    1.5086   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6465    1.8929   -1.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171    3.1555   -2.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    4.0520   -2.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191    5.3003   -2.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    3.6515   -1.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7467    2.4192   -1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0457   -0.0918   -0.0196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3279   -1.1845    0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251   -1.4532    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216   -2.5963    1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2451   -2.8461    2.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770   -3.5138    2.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -3.2686    1.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6926   -4.1929    1.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -2.1187    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602   -1.7980    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241   -2.5919    0.6977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3953    1.1776   -0.4038 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8442    0.9038   -1.6653 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5331    1.4433    0.5737 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9325    1.7954    1.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3233    0.1878    0.8238 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5119    0.1738    0.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5069   -3.1714   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4546   -1.0974   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    0.7116    1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    1.2203   -2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    3.4538   -3.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    5.4194   -3.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5351    4.3588   -1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097    2.1247   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3750   -0.7160    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4960   -2.4965    3.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1552   -4.4445    2.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572   -4.2744    1.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8251    2.1520   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337    0.2948   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    2.2777    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.7794    1.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6645    0.1430    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1256   -0.4392    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
 28 29  1  0
 28  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 17  1  0
 17 18  1  0
 18 25  2  0
 25 23  1  0
 23 24  1  0
 23 22  2  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 25 26  1  0
 26 27  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  6  5  1  0
  5  4  1  0
  4 32  1  0
 32 33  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 32 30  1  0
 26  8  1  0
 16 10  1  0
 19 18  1  0
 31 49  1  0
 30 48  1  6
 28 46  1  6
 29 47  1  0
  6 36  1  1
 24 45  1  0
 22 44  1  0
 21 43  1  0
 19 42  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
  4 35  1  6
 32 50  1  1
 33 51  1  0
  3 34  1  0
M  END


  Mrv0541 02241223232D          

 33 36  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  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    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
   -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 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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579   -1.6500    0.0000 O   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
    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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249938

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)C(OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C=C2)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)17-18(13(25)12-10(24)5-9(23)6-11(12)31-17)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-24,26-28H,(H,29,30)/t14-,15-,16+,19-,21?/m0/s1

> <INCHI_KEY>
FNTJVYCFNVUBOL-MBIBTLSJSA-N

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.3604

> <EXACT_MASS>
462.07982604

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
42.62580438078876

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.47900456366666666

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.433973515846841

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7116471559069595

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868297480420305

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
107.162

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
CONECT   18   11    7   19                                                  
CONECT   19   18                                                            
CONECT   20    8   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27    5   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28    2   30                                                  
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3604 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

(2S,3S,4S,5R)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)C(OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C=C2)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)17-18(13(25)12-10(24)5-9(23)6-11(12)31-17)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-24,26-28H,(H,29,30)/t14-,15-,16+,19-,21?/m0/s1

InChI Key

FNTJVYCFNVUBOL-MBIBTLSJSA-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
Diospyros kaki	LOTUS Database	35616633
Diplusodon uninervius	LOTUS Database	35616633
Pteris vittata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glucuronides

Alternative Parents

Substituents

Flavonoid-3-o-glucuronide
Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Beta-hydroxy acid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Hydroxy acid
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.4	ALOGPS
logP	0.48	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.16 m³·mol⁻¹	ChemAxon
Polarizability	42.63 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22846027

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0249938)

MOL for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0249938 ((2s,3s,4s,5r)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)