NP-MRD: Showing NP-Card for 4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one (NP0164835)

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Record Information

Version

2.0

Created at

2022-09-02 23:47:37 UTC

Updated at

2022-09-02 23:47:38 UTC

NP-MRD ID

NP0164835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one

Description

4-(3,4-Dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. 4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one is found in Coutarea hexandra, Exostema mexicanum and Hintonia latiflora. 4-(3,4-Dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508222D          

 33 36  0  0  0  0            999 V2000
    0.0000   -2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    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  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
    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
    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 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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.8579    0.8250    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
    2.1434    2.0625    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   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
  1  2  1  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  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  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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  2  0  0  0  0
 26 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -1.3183    6.0908    0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633    4.9186    0.6481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    3.6631    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    2.5272    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    1.2709    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    0.1261    0.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1350    0.0509   -0.0389 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4786   -0.4488   -1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395   -0.1799   -1.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2785   -0.2967   -2.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6594   -0.0044   -2.9333 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745   -1.2550   -0.6927 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8118   -2.3097   -1.5680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990   -1.7604    0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7283   -2.0263    1.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7918   -0.8127    1.0261 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3078   -0.0176    2.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    1.1794    0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -0.0457    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349   -1.2750    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610   -1.5945   -1.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9903   -2.7789   -1.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697   -3.7062   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904   -4.9006   -0.5614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4343   -3.4117    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3074   -4.3482    1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1006   -2.2228    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3469   -0.0803    0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9966    1.0961    0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2678    1.0154    0.8370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3977    2.2542    0.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1014    2.3422    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    3.5876    0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286    6.0351    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576    6.1561    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6640    6.9805    0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    2.6564    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.0227    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010    0.8139   -1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1973   -1.3439   -3.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706    0.4345   -3.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7227    0.9354   -2.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643   -0.8199   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860   -3.0647   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -2.7665    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9829   -1.1908    1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -1.4141    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5703    0.6044    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346   -0.8984   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -3.0322   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -5.0820   -1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221   -4.1305    2.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5395   -1.9983    2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8061   -1.0474    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797    4.5026    0.8660 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  2  0
 18 32  1  0
 32 31  1  0
 31 29  1  0
 29 30  2  0
 29 28  1  0
 28 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 32 33  2  0
 33  3  1  0
 16  7  1  0
 19 18  1  0
 27 20  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  7 38  1  6
  9 39  1  1
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  1
 13 44  1  0
 14 45  1  6
 15 46  1  0
 16 47  1  1
 17 48  1  0
 28 54  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 26 52  1  0
 27 53  1  0
 33 55  1  0
M  END


  Mrv1533004161508222D          

 33 36  0  0  0  0            999 V2000
    0.0000   -2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    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  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
    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
    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 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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.8579    0.8250    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
    2.1434    2.0625    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   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
  1  2  1  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  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  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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  2  0  0  0  0
 26 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC2OC(CO)C(O)C(O)C2O)=C2C(OC(=O)C=C2C2=CC=C(O)C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-30-10-5-14-18(11(7-17(26)31-14)9-2-3-12(24)13(25)4-9)15(6-10)32-22-21(29)20(28)19(27)16(8-23)33-22/h2-7,16,19-25,27-29H,8H2,1H3

> <INCHI_KEY>
JZBHUVGJBWDUSA-UHFFFAOYSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.65011712957235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
-0.11987713099999955

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.020462516622743

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.062506925785726

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346264787

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
119.65159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

Traditional Name

4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC2OC(CO)C(O)C(O)C2O)=C2C(OC(=O)C=C2C2=CC=C(O)C(O)=C2)=C1

InChI Identifier

InChI=1S/C22H22O11/c1-30-10-5-14-18(11(7-17(26)31-14)9-2-3-12(24)13(25)4-9)15(6-10)32-22-21(29)20(28)19(27)16(8-23)33-22/h2-7,16,19-25,27-29H,8H2,1H3

InChI Key

JZBHUVGJBWDUSA-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
Coutarea hexandra	LOTUS Database	35616633
Exostema mexicanum	LOTUS Database	35616633
Hintonia latiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin-5-o-glycoside
Coumarin o-glycoside
4-phenylcoumarin
Neoflavonoid skeleton
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Lactone
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
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	0.51	ALOGPS
logP	-0.12	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.65 m³·mol⁻¹	ChemAxon
Polarizability	43.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one (NP0164835)

MOL for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

3D MOL for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

3D SDF for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

3D-SDF for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

PDB for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

3D PDB for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

SMILES for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

INCHI for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

Structure for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)

3D Structure for NP0164835 (4-(3,4-dihydroxyphenyl)-7-methoxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one)