NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0203988)

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Record Information

Version

2.0

Created at

2022-09-04 23:34:42 UTC

Updated at

2022-09-04 23:34:42 UTC

NP-MRD ID

NP0203988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

Description

3,4,5-Trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 3,4,5-Trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308171918092D          

 34 37  0  0  0  0            999 V2000
    3.5724   -0.4125    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
    4.2868    0.0000    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
    0.0000    0.0000    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
    4.2868    0.8250    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
   -0.7145   -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
   -0.7145   -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
    1.4289   -1.6500    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
    2.1434   -1.2375    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    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   -1.6500    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    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
   -4.2868   -1.6500    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
   -2.1434   -2.8875    0.0000 O   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 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
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 18  6  1  0  0  0  0
 18 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  2  0  0  0  0
 26 14  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 17  1  0  0  0  0
 30 20  2  0  0  0  0
 31 20  1  0  0  0  0
 32  8  1  0  0  0  0
 32 18  1  0  0  0  0
 33  9  1  0  0  0  0
 33 21  1  0  0  0  0
 34 19  1  0  0  0  0
 34 21  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    5.0892    0.4177   -3.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7147    0.6991   -2.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9757    1.2485   -2.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1274    0.4539   -1.0559 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8542   -0.1023   -1.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750    0.0906    0.0632 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8637   -0.2230   -0.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6809    0.4011    0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5164   -0.2684   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7492    0.3106    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551   -0.3447   -0.1656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    0.1459   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -0.7026   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5207   -0.3245   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5691   -1.2102   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3430   -2.4925   -0.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3713   -3.3700   -1.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0274   -2.8827   -1.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0053   -2.0119   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1703    1.4356    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3915    2.0670    0.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0438    2.1930    0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1056    3.3822    1.0917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145    1.6055    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483    2.3000    0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7985    3.6050    1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849    1.6935    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    2.4323    0.8357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8612   -0.8742    1.0334 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7494   -2.1824    0.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3249   -0.5489    1.1518 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9112   -1.5574    1.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9820   -0.4589   -0.2086 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0360   -1.6989   -0.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3267    1.8126   -1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518    1.4392   -0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4369    1.0873    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -1.3025   -0.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7971    0.6613    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6007   -0.8988   -0.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7828   -3.9863   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8182   -3.8925   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9596   -2.3142   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5057    2.9959    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639    4.2491    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064    3.3742    1.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105   -0.7391    2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -2.3477    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4310    0.4429    1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4458   -1.5804    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9925   -0.0199   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8353   -2.2096   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 29  1  0
 29 30  1  0
 29  6  1  0
  6  7  1  0
  7  8  1  0
  8 27  2  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 24  2  0
 24 10  1  0
 10 11  1  0
 11 12  1  0
 12 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10  9  2  0
  6  5  1  0
  5  4  1  0
  4 33  1  0
 33 34  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 33 31  1  0
  9  8  1  0
 22 24  1  0
 19 13  1  0
 32 50  1  0
 31 49  1  1
 29 47  1  1
 30 48  1  0
  6 37  1  1
 28 46  1  0
 26 45  1  0
 21 44  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
  9 38  1  0
  4 36  1  1
 33 51  1  1
 34 52  1  0
  3 35  1  0
M  END


  Mrv1652308171918092D          

 34 37  0  0  0  0            999 V2000
    3.5724   -0.4125    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
    4.2868    0.0000    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
    0.0000    0.0000    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
    4.2868    0.8250    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
   -0.7145   -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
   -0.7145   -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
    1.4289   -1.6500    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
    2.1434   -1.2375    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    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   -1.6500    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    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
   -4.2868   -1.6500    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
   -2.1434   -2.8875    0.0000 O   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 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
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 18  6  1  0  0  0  0
 18 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  2  0  0  0  0
 26 14  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 17  1  0  0  0  0
 30 20  2  0  0  0  0
 31 20  1  0  0  0  0
 32  8  1  0  0  0  0
 32 18  1  0  0  0  0
 33  9  1  0  0  0  0
 33 21  1  0  0  0  0
 34 19  1  0  0  0  0
 34 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(OC2=C(O)C(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C=C3)=C2)OC(C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O13/c22-7-3-1-6(2-4-7)18-15(27)13(25)10-8(32-18)5-9(11(23)12(10)24)33-21-17(29)14(26)16(28)19(34-21)20(30)31/h1-5,14,16-17,19,21-24,26-29H,(H,30,31)

> <INCHI_KEY>
NYUYYEQSDXJVQI-UHFFFAOYSA-N

> <FORMULA>
C21H18O13

> <MOLECULAR_WEIGHT>
478.362

> <EXACT_MASS>
478.07474064

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.9731917753966

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
0.20850590866666624

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.294554397830025

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.600550446285267

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731998670091275

> <JCHEM_POLAR_SURFACE_AREA>
223.66999999999993

> <JCHEM_REFRACTIVITY>
108.874

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-AUG-19         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+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  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    1    2   18                                                  
CONECT    7    3    4   22                                                  
CONECT    8    5   10   32                                                  
CONECT    9    5   11   33                                                  
CONECT   10    8   12   13                                                  
CONECT   11    9   12   23                                                  
CONECT   12   10   11   24                                                  
CONECT   13   10   15   25                                                  
CONECT   14   16   17   26                                                  
CONECT   15   13   18   27                                                  
CONECT   16   14   19   28                                                  
CONECT   17   14   21   29                                                  
CONECT   18    6   15   32                                                  
CONECT   19   16   20   34                                                  
CONECT   20   19   30   31                                                  
CONECT   21   17   33   34                                                  
CONECT   22    7                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   20                                                            
CONECT   31   20                                                            
CONECT   32    8   18                                                       
CONECT   33    9   21                                                       
CONECT   34   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₁H₁₈O₁₃

Average Mass

478.3620 Da

Monoisotopic Mass

478.07474 Da

IUPAC Name

3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)C(OC2=C(O)C(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C=C3)=C2)OC(C1O)C(O)=O

InChI Identifier

InChI=1S/C21H18O13/c22-7-3-1-6(2-4-7)18-15(27)13(25)10-8(32-18)5-9(11(23)12(10)24)33-21-17(29)14(26)16(28)19(34-21)20(30)31/h1-5,14,16-17,19,21-24,26-29H,(H,30,31)

InChI Key

NYUYYEQSDXJVQI-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Aryl ketone
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Furan
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.16	ALOGPS
logP	0.21	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.87 m³·mol⁻¹	ChemAxon
Polarizability	43.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0125387

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB084299

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

75307446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0203988)

MOL for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0203988 (3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)