NP-MRD: Showing NP-Card for 6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one (NP0056447)

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Record Information

Version

2.0

Created at

2022-04-28 02:13:45 UTC

Updated at

2022-04-28 02:13:45 UTC

NP-MRD ID

NP0056447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one

Description

6A,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Thus, 6a,12b-dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one is considered to be a flavonoid. 6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one is found in Burkea africana . Based on a literature review very few articles have been published on 6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204132D          

 32 36  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  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
    1.4289   -0.0000    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 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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  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  5  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  9 19  1  6  0  0  0
 14 20  1  0  0  0  0
 13 21  1  0  0  0  0
 12 22  1  0  0  0  0
  8 23  1  1  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
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 25 31  1  0  0  0  0
  2 32  1  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
   -0.9243   -4.0138    0.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914   -2.9573    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2416   -2.5512   -0.4165 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4020   -1.1657   -0.6294 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6153   -0.5194    0.7223 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0765   -0.4743    0.9576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6827   -1.3753    1.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -1.3649    2.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5183   -2.3270    2.9178 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510   -0.4398    1.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2104   -0.3997    1.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2624    0.4867    0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    1.4183   -0.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    0.4535    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    0.8107    0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0883    1.5963   -0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    2.9454   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056    3.6592   -1.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156    5.0370   -1.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    2.9686   -2.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8292    1.6021   -2.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.8989   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7985   -0.5582   -1.3461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0346   -0.9562   -0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0776   -2.1184    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2383   -2.4922    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3738   -1.7052    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5040   -2.1057    1.3706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3388   -0.5634   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487    0.2684   -0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1696   -0.1944   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.9841   -1.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -0.9865   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977   -1.0779    1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0289   -2.1048    2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -2.3439    3.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7342   -1.0061    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7180    2.1113   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4807    1.1943   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5323    3.4761    0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    5.6430   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930    3.5213   -3.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.1134   -3.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209   -0.9881   -2.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784   -3.3747    1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3488   -1.6051    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3066    0.0380    0.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483    1.5428   -1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 22  2  0
 22 21  1  0
 21 20  2  0
 22 23  1  0
 23  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 24  2  0
  4  5  1  0
  5 15  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 20 18  1  0
 24 23  1  0
 14  6  1  0
 15 16  1  0
 24 25  1  0
 19 41  1  0
 17 40  1  0
 21 43  1  0
 20 42  1  0
 23 44  1  6
  4 33  1  6
 26 45  1  0
 28 46  1  0
 30 47  1  0
 32 48  1  0
  5 34  1  1
  7 35  1  0
  9 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
M  END


  Mrv1652304282204132D          

 32 36  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  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
    1.4289   -0.0000    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 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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  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  5  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  9 19  1  6  0  0  0
 14 20  1  0  0  0  0
 13 21  1  0  0  0  0
 12 22  1  0  0  0  0
  8 23  1  1  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
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 25 31  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)[C@H]1[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C13)[C@H](O2)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H16O10/c23-8-1-2-9-14(5-8)31-20(7-3-11(24)17(27)12(25)4-7)21-16(9)15-10(22(30)32-21)6-13(26)18(28)19(15)29/h1-6,16,20-21,23-29H/t16-,20-,21+/m1/s1

> <INCHI_KEY>
FDVGUFRMRNGBAK-HBGVWJBISA-N

> <FORMULA>
C22H16O10

> <MOLECULAR_WEIGHT>
440.36

> <EXACT_MASS>
440.074346715

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
41.346384439889135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10S)-5,15,16,17-tetrahydroxy-9-(3,4,5-trihydroxyphenyl)-8,11-dioxatetracyclo[8.8.0.0^{2,7}.0^{13,18}]octadeca-2(7),3,5,13,15,17-hexaen-12-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.705241882

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.767342513644808

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8490697467672375

> <JCHEM_PKA_STRONGEST_BASIC>
-4.915038954804779

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
108.27299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10S)-5,15,16,17-tetrahydroxy-9-(3,4,5-trihydroxyphenyl)-8,11-dioxatetracyclo[8.8.0.0^{2,7}.0^{13,18}]octadeca-2(7),3,5,13,15,17-hexaen-12-one

> <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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    9                                                       
CONECT   20   14                                                            
CONECT   21   13                                                            
CONECT   22   12                                                            
CONECT   23    8   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27                                                            
CONECT   30   26                                                            
CONECT   31   25                                                            
CONECT   32    2                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₁₆O₁₀

Average Mass

440.3600 Da

Monoisotopic Mass

440.07435 Da

IUPAC Name

(1R,9R,10S)-5,15,16,17-tetrahydroxy-9-(3,4,5-trihydroxyphenyl)-8,11-dioxatetracyclo[8.8.0.0^{2,7}.0^{13,18}]octadeca-2(7),3,5,13,15,17-hexaen-12-one

Traditional Name

(1R,9R,10S)-5,15,16,17-tetrahydroxy-9-(3,4,5-trihydroxyphenyl)-8,11-dioxatetracyclo[8.8.0.0^{2,7}.0^{13,18}]octadeca-2(7),3,5,13,15,17-hexaen-12-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1)[C@H]1[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C13)[C@H](O2)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C22H16O10/c23-8-1-2-9-14(5-8)31-20(7-3-11(24)17(27)12(25)4-7)21-16(9)15-10(22(30)32-21)6-13(26)18(28)19(15)29/h1-6,16,20-21,23-29H/t16-,20-,21+/m1/s1

InChI Key

FDVGUFRMRNGBAK-HBGVWJBISA-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
Burkea africana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Gallic acid or derivatives
Chromane
Benzopyran
Isochromane
1-benzopyran
2-benzopyran
Pyrogallol derivative
Benzenetriol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Oxacycle
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020016 )

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	2.55	ALOGPS
logP	2.71	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.27 m³·mol⁻¹	ChemAxon
Polarizability	41.35 Å³	ChemAxon
Number of Rings	5	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

C00009323

Chemspider ID

24842499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14463113

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one (NP0056447)

MOL for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

3D MOL for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

3D SDF for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

3D-SDF for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

PDB for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

3D PDB for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

SMILES for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

INCHI for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

Structure for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)

3D Structure for NP0056447 (6a,12b-Dihydro-3,10,11,12-tetrahydroxy-6-(3,4,5-trihydroxyphenyl)-[2]benzopyrano[3,4-c]benzopyran-8(6H)-one)