NP-MRD: Showing NP-Card for Apigenin 7-O-glucuronide methyl ester (NP0076172)

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Record Information

Version

2.0

Created at

2022-04-28 21:19:56 UTC

Updated at

2022-04-28 21:19:56 UTC

NP-MRD ID

NP0076172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apigenin 7-O-glucuronide methyl ester

Description

Apigenin 7-(6''-methylglucuronide) 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, apigenin 7-(6''-methylglucuronide) is considered to be a flavonoid. Apigenin 7-O-glucuronide methyl ester is found in Aster indicus, Bellis perennis, Broussonetia papyrifera, Chaenomeles sinensis, Erigeron annuus, Helichrysum arenarium, Hyssopus officinalis, Meehania fargesii, Ocimum tenuiflorum and Physocarpus capitatus. Apigenin 7-O-glucuronide methyl ester was first documented in 2005 (PMID: 16061337). Based on a literature review a small amount of articles have been published on Apigenin 7-(6''-methylglucuronide) (PMID: 21815723).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223192D          

 33 36  0  0  1  0            999 V2000
    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   -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
   -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
   -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
   -3.5724   -2.8875    0.0000 O   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
    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
    2.8579   -1.6500    0.0000 O   0  0  0  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  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  2  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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.8579    0.0000    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  2 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
  1 18  2  0  0  0  0
 17 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  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 30  1  6  0  0  0
 22 31  1  1  0  0  0
 21 32  1  6  0  0  0
 15 33  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -7.2999    0.0418   -3.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6856   -0.1331   -1.9223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3304    0.1125   -1.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6493    0.4990   -2.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6680   -0.0618   -0.4074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3408    0.2556   -0.5235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.2265    0.6999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3263    0.5068    0.4185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201   -0.2560    0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257   -1.4974    1.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8382   -2.2243    1.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7647   -3.4998    2.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0683   -1.7232    1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2391   -2.4408    1.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1566   -3.5664    1.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4294   -1.8660    0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -0.6189    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7689   -0.0038   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9889   -0.6110   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1746   -0.0109   -0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1271    1.2335   -0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3079    1.8352   -1.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9195    1.8770   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7426    1.2480   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.0125    0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961   -0.4797    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377    0.2340    0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613    1.2352    1.6764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7843    0.6297    2.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047    1.9234    0.9644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9420    2.4911   -0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3989    0.8184    0.5848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7330    0.1012    1.7109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1065   -0.7106   -3.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8237    1.0403   -3.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5548    0.0459   -3.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242   -1.1447   -0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -0.7606    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743   -1.9419    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -3.8647    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3433   -2.4261    1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0779   -1.5851    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1359   -0.5099   -0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1921    1.3839   -1.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9131    2.8574   -1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8178    1.7805   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.2292   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5142    1.9995    1.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -0.1813    3.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8884    2.6823    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    2.6270   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3148    1.2731    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7113   -0.0828    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
  7 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  5  1  0
 27  9  1  0
 24 18  1  0
 26 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  7 38  1  1
 10 39  1  0
 12 40  1  0
 16 41  1  0
 27 47  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 28 48  1  1
 29 49  1  0
 30 50  1  1
 31 51  1  0
 32 52  1  6
 33 53  1  0
M  END


  Mrv1652304282223192D          

 33 36  0  0  1  0            999 V2000
    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   -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
   -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
   -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
   -3.5724   -2.8875    0.0000 O   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
    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
    2.8579   -1.6500    0.0000 O   0  0  0  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  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  2  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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.8579    0.0000    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  2 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
  1 18  2  0  0  0  0
 17 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  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 30  1  6  0  0  0
 22 31  1  1  0  0  0
 21 32  1  6  0  0  0
 15 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076172

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-11-6-12(24)16-13(25)8-14(32-15(16)7-11)9-2-4-10(23)5-3-9/h2-8,17-20,22-24,26-28H,1H3/t17-,18-,19+,20-,22+/m0/s1

> <INCHI_KEY>
XXKIWCKZQFBXIR-SXFAUFNYSA-N

> <FORMULA>
C22H20O11

> <MOLECULAR_WEIGHT>
460.391

> <EXACT_MASS>
460.100561464

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.42289296894208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylate

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.9047896343333338

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.741327959315846

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.29761906880957

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868312099437173

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
109.69479999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylate

> <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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    7   18                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15    2   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17    1                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   32                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
CONECT   32   21                                                            
CONECT   33   15                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₁

Average Mass

460.3910 Da

Monoisotopic Mass

460.10056 Da

IUPAC Name

methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylate

Traditional Name

methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H20O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-11-6-12(24)16-13(25)8-14(32-15(16)7-11)9-2-4-10(23)5-3-9/h2-8,17-20,22-24,26-28H,1H3/t17-,18-,19+,20-,22+/m0/s1

InChI Key

XXKIWCKZQFBXIR-SXFAUFNYSA-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
Aster indicus	LOTUS Database	35616633
Bellis perennis	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Erigeron annuus	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Hyssopus officinalis L.	LOTUS Database	35616633
Meehania fargesii	LOTUS Database	35616633
Ocimum tenuiflorum	LOTUS Database	35616633
Physocarpus capitatus	Plant	KNApSAcK

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
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
Chromone
O-glycosyl compound
Benzopyran
1-benzopyran
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Methyl ester
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Acetal
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	1.32	ALOGPS
logP	0.9	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.69 m³·mol⁻¹	ChemAxon
Polarizability	44.42 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	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

23340695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13844658

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hammoud L, Seghiri R, Benayache S, Mosset P, Lobstein A, Chaabi M, Leon F, Brouard I, Bermejo J, Benayache F: A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M. Nat Prod Res. 2012;26(3):203-8. doi: 10.1080/14786419.2010.534995. Epub 2011 Aug 4. [PubMed:21815723 ]
Nazaruk J, Jakoniuk P: Flavonoid composition and antimicrobial activity of Cirsium rivulare (Jacq.) All. flowers. J Ethnopharmacol. 2005 Nov 14;102(2):208-12. doi: 10.1016/j.jep.2005.06.012. Epub 2005 Aug 2. [PubMed:16061337 ]

Showing NP-Card for Apigenin 7-O-glucuronide methyl ester (NP0076172)

MOL for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

3D MOL for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

3D SDF for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

3D-SDF for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

PDB for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

3D PDB for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

SMILES for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

INCHI for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

Structure for NP0076172 (Apigenin 7-O-glucuronide methyl ester)

3D Structure for NP0076172 (Apigenin 7-O-glucuronide methyl ester)