NP-MRD: Showing NP-Card for 7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one (NP0059960)

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Record Information

Version

2.0

Created at

2022-04-28 05:05:33 UTC

Updated at

2022-04-28 05:05:33 UTC

NP-MRD ID

NP0059960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one

Description

(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-2-(hydroxymethyl)oxan-3-yl acetate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one is found in Calicotome villosa . Based on a literature review very few articles have been published on (2S,3S,4R,5R,6S)-4,5-dihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-2-(hydroxymethyl)oxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207052D          

 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
    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
   -1.4289    0.8250    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
   -2.1434    2.0625    0.0000 C   0  0  2  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
   -0.7145    2.0625    0.0000 C   0  0  1  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
    0.0000    2.4750    0.0000 C   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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   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
   -2.8579    0.8250    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
  3 18  1  0  0  0  0
  1 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  1  0  0  0
 21 33  1  6  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -7.8200   -0.7313    0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3237   -0.7816    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7750   -1.7224    1.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5462    0.1738   -0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1145    0.1351   -0.0393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6287    1.3245    0.7075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5442    2.4988    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2833    3.5850    1.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    1.6314    0.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    0.8543   -0.3309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2881   -0.4053    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174   -0.9351    0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -2.2159    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709   -2.8035    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3990   -4.0675    1.4706 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5313   -2.1148    0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -2.6483    0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9344   -3.7959    1.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8778   -1.8328    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108   -0.5669    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8689    0.2512   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.5480   -0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7249    2.3711   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0188    1.9116   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2547    0.6368   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1682   -0.1519   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849   -0.1254   -0.0548 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -0.8245    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1430   -0.2628    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    0.7064   -1.6516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3791    1.9376   -2.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6806    0.0861   -1.4742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6879   -1.2667   -1.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2518   -1.1268    1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1291    0.3473    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2431   -1.2446   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394   -0.7755    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213    1.1257    1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4341    2.8212   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079    2.2305    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4314    4.0047    0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6936    1.4242   -0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -2.8004    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -4.7158    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8415   -2.3093    0.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6833    1.9092   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5746    3.3725   -1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8842    2.5072   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353    0.2284   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3781   -1.1426    0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    0.7479   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127    0.0163   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986    2.0848   -2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079    0.6505   -2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -1.7546   -1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 27  1  0
 27 28  1  0
 28 29  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 10 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  5  1  0
 29 12  1  0
 26 21  1  0
 28 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  6 38  1  1
  7 39  1  0
  7 40  1  0
  8 41  1  0
 10 42  1  6
 13 43  1  0
 15 44  1  0
 19 45  1  0
 29 51  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 30 52  1  6
 31 53  1  0
 32 54  1  6
 33 55  1  0
M  END


  Mrv1652304282207052D          

 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
    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
   -1.4289    0.8250    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
   -2.1434    2.0625    0.0000 C   0  0  2  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
   -0.7145    2.0625    0.0000 C   0  0  1  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
    0.0000    2.4750    0.0000 C   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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   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
   -2.8579    0.8250    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
  3 18  1  0  0  0  0
  1 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  1  0  0  0
 21 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0059960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H](CO)O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=CC=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O10/c1-11(25)30-22-18(10-24)33-23(21(29)20(22)28)31-13-7-14(26)19-15(27)9-16(32-17(19)8-13)12-5-3-2-4-6-12/h2-9,18,20-24,26,28-29H,10H2,1H3/t18-,20+,21+,22+,23+/m0/s1

> <INCHI_KEY>
DRNKLAZUHQQSNP-UTCUMILBSA-N

> <FORMULA>
C23H22O10

> <MOLECULAR_WEIGHT>
458.419

> <EXACT_MASS>
458.121296908

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.013053837204964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.183311772333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.257093351471559

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.314216273958318

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981808913290407

> <JCHEM_POLAR_SURFACE_AREA>
151.98

> <JCHEM_REFRACTIVITY>
112.22889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-[(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxy]-2-(hydroxymethyl)oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
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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       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    3                                                            
CONECT   19    1   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   33                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   22                                                            
CONECT   33   21                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4R,5R,6S)-4,5-Dihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-2-(hydroxymethyl)oxan-3-yl acetic acid	Generator

Chemical Formula

C₂₃H₂₂O₁₀

Average Mass

458.4190 Da

Monoisotopic Mass

458.12130 Da

IUPAC Name

(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-2-(hydroxymethyl)oxan-3-yl acetate

Traditional Name

(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-[(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxy]-2-(hydroxymethyl)oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H](CO)O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=CC=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H22O10/c1-11(25)30-22-18(10-24)33-23(21(29)20(22)28)31-13-7-14(26)19-15(27)9-16(32-17(19)8-13)12-5-3-2-4-6-12/h2-9,18,20-24,26,28-29H,10H2,1H3/t18-,20+,21+,22+,23+/m0/s1

InChI Key

DRNKLAZUHQQSNP-UTCUMILBSA-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
Calicotome villosa	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	1.38	ALOGPS
logP	1.18	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.23 m³·mol⁻¹	ChemAxon
Polarizability	45.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163103889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one (NP0059960)

MOL for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

3D MOL for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

3D SDF for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

3D-SDF for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

PDB for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

3D PDB for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

SMILES for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

INCHI for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

Structure for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)

3D Structure for NP0059960 (7-[(4-O-Acetyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one)