NP-MRD: Showing NP-Card for methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate (NP0320584)

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Record Information

Version

2.0

Created at

2022-09-11 22:18:58 UTC

Updated at

2022-09-11 22:18:58 UTC

NP-MRD ID

NP0320584

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate

Description

Methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylate 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. methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate is found in Oroxylum indicum. Methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161502172D          

 34 37  0  0  0  0            999 V2000
   -2.1434    3.7125    0.0000 C   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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    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
    2.8579    0.0000    0.0000 O   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
    3.5724   -1.2375    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
    2.8579   -2.4750    0.0000 O   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
    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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    7.3003    2.3204   -1.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    1.0498   -0.8313 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3231    0.9371   -0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639    1.9531   -1.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5820   -0.3233   -0.6967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2275   -0.1887   -0.8696 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906   -0.8847    0.1299 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1675   -0.8609   -0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0421   -0.3221    0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703   -0.6753   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -0.1771    0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    0.7150    1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641    1.0756    1.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2814    1.9352    2.8219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.5420    1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914    0.9416    2.0213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    2.1412    1.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404    1.2060    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250    1.4326    2.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7915    1.4166    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6106    0.4913   -0.6959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9235   -0.1461   -0.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3730   -1.2240   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5937   -1.8184   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4191   -1.3578   -1.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9878   -0.2840   -2.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7557    0.3075   -1.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5889   -0.4672   -0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0735   -2.3102    0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2606   -2.6715   -1.2757 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3860   -2.2579    0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2741   -3.2075    0.2965 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9888   -0.8584    0.6459 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3977   -0.9669    0.6220 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6434    2.8663   -1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3200    2.1790   -1.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3482    2.9153   -0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.0581   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7646   -0.3979    1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363   -1.3545   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219    2.3969    3.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8450    2.0059    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    2.9423    2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    2.4348    0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7138    2.4708    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7951    1.3017    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3303    1.0869   -1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255   -1.5984    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9291   -2.6571    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3880   -1.8237   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6270    0.0903   -3.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4196    1.1472   -2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3671   -3.0442    0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -3.1303   -1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2596   -2.4298    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0080   -3.3633    0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -0.2110    1.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8226   -0.2322    1.1322 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  2  0
 12 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 28  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
  7 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  5  1  0
 15  9  1  0
 28 11  1  0
 27 22  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  6
  7 39  1  1
 10 40  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  6
 23 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 29 53  1  1
 30 54  1  0
 31 55  1  1
 32 56  1  0
 33 57  1  1
 34 58  1  0
M  END


  Mrv1533004161502172D          

 34 37  0  0  0  0            999 V2000
   -2.1434    3.7125    0.0000 C   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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    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
    2.8579    0.0000    0.0000 O   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
    3.5724   -1.2375    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
    2.8579   -2.4750    0.0000 O   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
    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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC(OC2=CC3=C(C(=O)CC(O3)C3=CC=CC=C3)C(O)=C2OC)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O11/c1-30-20-14(33-23-19(28)17(26)18(27)21(34-23)22(29)31-2)9-13-15(16(20)25)11(24)8-12(32-13)10-6-4-3-5-7-10/h3-7,9,12,17-19,21,23,25-28H,8H2,1-2H3

> <INCHI_KEY>
LBZIUNBOFOPEBU-UHFFFAOYSA-N

> <FORMULA>
C23H24O11

> <MOLECULAR_WEIGHT>
476.434

> <EXACT_MASS>
476.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.7180196015358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylate

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.179102607

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.164860271265956

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.210269475220638

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686832425179702

> <JCHEM_POLAR_SURFACE_AREA>
161.21

> <JCHEM_REFRACTIVITY>
112.55300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -0.770   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+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       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    9   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   13   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29    7   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₄O₁₁

Average Mass

476.4340 Da

Monoisotopic Mass

476.13186 Da

IUPAC Name

methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylate

Traditional Name

methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(OC2=CC3=C(C(=O)CC(O3)C3=CC=CC=C3)C(O)=C2OC)C(O)C(O)C1O

InChI Identifier

InChI=1S/C23H24O11/c1-30-20-14(33-23-19(28)17(26)18(27)21(34-23)22(29)31-2)9-13-15(16(20)25)11(24)8-12(32-13)10-6-4-3-5-7-10/h3-7,9,12,17-19,21,23,25-28H,8H2,1-2H3

InChI Key

LBZIUNBOFOPEBU-UHFFFAOYSA-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
Oroxylum indicum	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
6-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Fatty acyl glycoside
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
O-glycosyl compound
Chromone
Glycosyl compound
Chromane
1-benzopyran
Benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Beta-hydroxy acid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monosaccharide
Benzenoid
Fatty acyl
Hydroxy acid
Monocyclic benzene moiety
Pyran
Oxane
Methyl ester
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
Alcohol
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	1.02	ALOGPS
logP	1.18	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	161.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.55 m³·mol⁻¹	ChemAxon
Polarizability	46.72 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

24750588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate (NP0320584)

MOL for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

3D MOL for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

3D SDF for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

3D-SDF for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

PDB for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

3D PDB for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

SMILES for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

INCHI for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

Structure for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)

3D Structure for NP0320584 (methyl 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl)oxy]oxane-2-carboxylate)