NP-MRD: Showing NP-Card for (1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0231258)

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Record Information

Version

2.0

Created at

2022-09-06 12:01:55 UTC

Updated at

2022-09-06 12:01:55 UTC

NP-MRD ID

NP0231258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Description

(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. (1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol is found in Rumex acetosa. Based on a literature review very few articles have been published on (1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062214012D          

 51 58  0  0  1  0            999 V2000
    9.8968   -1.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855   -1.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4679   -1.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566   -1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390   -1.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7630   -0.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0518   -0.0055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3341   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3277   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6575   -1.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6101   -1.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988   -1.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9052   -0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229    0.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292    0.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3469    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3533    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6420    2.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484    3.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660    3.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724    4.5374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0773    3.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7949    3.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709    2.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0581    0.8195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7758    1.2264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264    0.1864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5014    0.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941    0.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819    1.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    1.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9110    0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1158    0.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072   -1.2110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860   -1.7988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1644   -2.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -3.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400   -3.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212   -4.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -4.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -3.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3457   -2.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110   -1.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544   -0.9113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5800   -1.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4807   -0.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4870    0.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1919   -0.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 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
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 16 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 13  1  6  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  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 38 45  1  0  0  0  0
 37 46  1  0  0  0  0
 12 46  1  0  0  0  0
 37 47  1  0  0  0  0
 27 47  1  0  0  0  0
 47 48  1  1  0  0  0
  6 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
  2 51  1  0  0  0  0
M  END


  Mrv1652309062214012D          

 51 58  0  0  1  0            999 V2000
    9.8968   -1.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855   -1.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4679   -1.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566   -1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390   -1.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7630   -0.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0518   -0.0055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3341   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3277   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6575   -1.9937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6101   -1.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988   -1.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9052   -0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229    0.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292    0.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3469    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3533    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6420    2.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484    3.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3660    3.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724    4.5374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0773    3.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7949    3.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709    2.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0581    0.8195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7758    1.2264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264    0.1864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5014    0.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941    0.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819    1.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    1.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9110    0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1158    0.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072   -1.2110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860   -1.7988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1644   -2.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -3.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400   -3.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212   -4.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996   -4.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -3.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3457   -2.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110   -1.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544   -0.9113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5800   -1.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4807   -0.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4870    0.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1919   -0.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 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
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 16 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 13  1  6  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  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 38 45  1  0  0  0  0
 37 46  1  0  0  0  0
 12 46  1  0  0  0  0
 37 47  1  0  0  0  0
 27 47  1  0  0  0  0
 47 48  1  1  0  0  0
  6 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
  2 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231258

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](OC2=C3[C@@H]4[C@@H](O)[C@@](OC5=CC(O)=CC(O)=C45)(OC3=CC(O)=C2[C@@H]1C1=C(O)C=C(O)C=C1O)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C36H28O15/c37-14-7-20(43)26(21(44)8-14)30-28-23(46)11-25-29(34(28)49-33(32(30)47)12-1-3-16(39)18(41)5-12)31-27-22(45)9-15(38)10-24(27)50-36(51-25,35(31)48)13-2-4-17(40)19(42)6-13/h1-11,30-33,35,37-48H/t30-,31+,32+,33+,35+,36-/m0/s1

> <INCHI_KEY>
NTQCIMZZEOAJFR-BXSVKRRSSA-N

> <FORMULA>
C36H28O15

> <MOLECULAR_WEIGHT>
700.605

> <EXACT_MASS>
700.142820202

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
68.73903747909299

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <JCHEM_LOGP>
4.178612930666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.060649269719985

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.640286675918565

> <JCHEM_PKA_STRONGEST_BASIC>
-5.16294574906392

> <JCHEM_POLAR_SURFACE_AREA>
270.44999999999993

> <JCHEM_REFRACTIVITY>
174.7056

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      18.474  -3.131   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      17.146  -2.351   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.807  -3.111   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.479  -2.331   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.139  -3.090   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.491  -0.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.163  -0.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.824  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.812  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.427  -3.722   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.472  -3.070   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.144  -2.289   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.156  -0.749   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.496   0.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.508   1.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.848   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.859   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.532   4.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.544   6.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.883   6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.895   8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.211   6.150   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.551   6.909   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.199   4.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.175   1.530   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.515   2.289   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.076   0.348   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.536   0.360   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.149   1.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.246   2.931   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.665   2.261   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.567   1.180   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.083   1.590   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.954  -0.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.439  -0.721   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.427  -2.261   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.507  -3.358   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.907  -4.776   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.835  -6.005   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.235  -7.423   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.706  -7.612   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.106  -9.031   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.778  -6.383   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.250  -6.573   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.379  -4.965   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.047  -3.370   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.755  -1.701   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       8.549  -3.020   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      15.831  -0.031   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      15.842   1.509   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      17.158  -0.811   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   49                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   46                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   16    7   26                                                  
CONECT   26   25                                                            
CONECT   27   13   28   47                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   28   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   46   47                                             
CONECT   38   37   39   45                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   38                                                       
CONECT   46   37   12                                                       
CONECT   47   37   27   48                                                  
CONECT   48   47                                                            
CONECT   49    6   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49    2                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₂₈O₁₅

Average Mass

700.6050 Da

Monoisotopic Mass

700.14282 Da

IUPAC Name

(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Traditional Name

(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](OC2=C3[C@@H]4[C@@H](O)[C@@](OC5=CC(O)=CC(O)=C45)(OC3=CC(O)=C2[C@@H]1C1=C(O)C=C(O)C=C1O)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C36H28O15/c37-14-7-20(43)26(21(44)8-14)30-28-23(46)11-25-29(34(28)49-33(32(30)47)12-1-3-16(39)18(41)5-12)31-27-22(45)9-15(38)10-24(27)50-36(51-25,35(31)48)13-2-4-17(40)19(42)6-13/h1-11,30-33,35,37-48H/t30-,31+,32+,33+,35+,36-/m0/s1

InChI Key

NTQCIMZZEOAJFR-BXSVKRRSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rumex acetosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

A-type proanthocyanidin
Proanthocyanidin
Bi- and polyflavonoid skeleton
Catechin
Pyranoflavonoid
Linear 1,7-diphenylheptane skeleton
Pyranoneoflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
5-hydroxyflavonoid
4'-hydroxyflavonoid
Neoflavonoid skeleton
Neoflavan
Flavan
Pyranochromene
Chromane
Benzopyran
1-benzopyran
Benzenetriol
Phloroglucinol derivative
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Ketal
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	4.18	ChemAxon
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	270.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	174.71 m³·mol⁻¹	ChemAxon
Polarizability	68.74 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162910389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (NP0231258)

MOL for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D MOL for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D SDF for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D-SDF for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

PDB for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D PDB for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

SMILES for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

INCHI for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

Structure for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)

3D Structure for NP0231258 ((1r,5r,6r,7s,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-7-(2,4,6-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol)