NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate (NP0315339)

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Record Information

Version

2.0

Created at

2022-09-11 13:55:39 UTC

Updated at

2022-09-11 13:55:39 UTC

NP-MRD ID

NP0315339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

Description

Spectaflavoside A 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''. (2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate is found in Zingiber spectabile. (2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate was first documented in 2012 (PMID: 22546674). Based on a literature review very few articles have been published on spectaflavoside A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112215552D          

 68 75  0  0  1  0            999 V2000
    2.8579    5.7750    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
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    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    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   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
    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5749    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
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 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
 37 48  1  0  0  0  0
 48 49  1  1  0  0  0
 35 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  2  0  0  0  0
 51 57  1  0  0  0  0
 50 58  1  0  0  0  0
 58 59  1  0  0  0  0
 26 59  2  0  0  0  0
 32 59  1  0  0  0  0
 25 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
 21 62  1  0  0  0  0
 62 63  1  0  0  0  0
 11 63  1  0  0  0  0
 63 64  2  0  0  0  0
  9 65  1  0  0  0  0
 65 66  1  6  0  0  0
 65 67  1  0  0  0  0
  5 67  1  0  0  0  0
 67 68  1  6  0  0  0
M  END

     RDKit          3D

110117  0  0  0  0  0  0  0  0999 V2000
   11.3391   -0.5888   -4.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1571   -0.9091   -3.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0082   -2.1002   -3.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2251    0.0413   -2.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1411   -0.3626   -2.1901 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1813    0.3661   -0.8598 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4512   -0.5965    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0639    1.1368   -0.6576 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9440    0.3507   -0.6396 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8401    1.1627   -0.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9889    0.6695    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733    0.8604    2.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748    1.6244    2.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0833    2.5068    2.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1550    3.1670    2.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4307    2.9240    3.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3570   -0.9417    3.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5031   -2.9630   -0.3103 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0260    0.0407   -3.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112215552D          

 68 75  0  0  1  0            999 V2000
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  5 67  1  0  0  0  0
 67 68  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0315339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=C(C(O)=C3C2=O)C2=C3OC(C4=CC=C(O)C=C4)=C(O[C@@H]4O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]4O)C(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C46H42O22/c1-15-38(63-17(3)47)34(57)36(59)45(61-15)67-43-32(55)29-24(52)13-23(51)28(42(29)66-41(43)20-7-11-22(50)12-8-20)27-25(53)14-26-30(31(27)54)33(56)44(40(65-26)19-5-9-21(49)10-6-19)68-46-37(60)35(58)39(16(2)62-46)64-18(4)48/h5-16,34-39,45-46,49-54,57-60H,1-4H3/t15-,16-,34-,35-,36+,37+,38-,39-,45-,46-/m0/s1

> <INCHI_KEY>
UIUPYGWVOAFVLA-GWYUDNFRSA-N

> <FORMULA>
C46H42O22

> <MOLECULAR_WEIGHT>
946.82

> <EXACT_MASS>
946.216772992

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
91.56188080337616

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-6-[(3'-{[(2S,3R,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-4H,4'H-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <JCHEM_LOGP>
2.967510351333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.378572141178226

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.599157004451516

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9548234628223957

> <JCHEM_POLAR_SURFACE_AREA>
344.42

> <JCHEM_REFRACTIVITY>
228.88299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-6-[(3'-{[(2S,3R,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   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  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      18.672   4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.005   2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      20.005  -0.770   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      21.339   0.000   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      22.673   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.006   1.540   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      25.340   2.310   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      26.674   1.540   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      28.007   2.310   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      26.674   0.000   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      25.340  -0.770   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      22.673  -2.310   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   67                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   65                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   63                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   12   21                                                       
CONECT   21   20   22   62                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   60                                                  
CONECT   26   25   27   59                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   59                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   50                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   48                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   37   49                                                  
CONECT   49   48                                                            
CONECT   50   35   51   58                                                  
CONECT   51   50   52   57                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   51                                                       
CONECT   58   50   59                                                       
CONECT   59   58   26   32                                                  
CONECT   60   25   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   21   63                                                  
CONECT   63   62   11   64                                                  
CONECT   64   63                                                            
CONECT   65    9   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65    5   68                                                  
CONECT   68   67                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  150    0
END

View in JSmol

Synonyms

Value	Source
3-O-(4'-O-Acetyl)-alpha-L-rhamnopyranoside-(I-6,II-8)-kaempferol-3-O-(4'-O-acetyl)-alpha-L-rhamnopyranoside	MeSH
3-O-(4'-O-Acetyl)rhamnopyranoside-(I-6,II-8)-kaempferol-3-O-(4'-O-acetyl)rhamnopyranoside	MeSH

Chemical Formula

C₄₆H₄₂O₂₂

Average Mass

946.8200 Da

Monoisotopic Mass

946.21677 Da

IUPAC Name

(2S,3R,4S,5R,6S)-6-[(3'-{[(2S,3R,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-4H,4'H-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

Traditional Name

(2S,3R,4S,5R,6S)-6-[(3'-{[(2S,3R,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=C(C(O)=C3C2=O)C2=C3OC(C4=CC=C(O)C=C4)=C(O[C@@H]4O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]4O)C(=O)C3=C(O)C=C2O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C46H42O22/c1-15-38(63-17(3)47)34(57)36(59)45(61-15)67-43-32(55)29-24(52)13-23(51)28(42(29)66-41(43)20-7-11-22(50)12-8-20)27-25(53)14-26-30(31(27)54)33(56)44(40(65-26)19-5-9-21(49)10-6-19)68-46-37(60)35(58)39(16(2)62-46)64-18(4)48/h5-16,34-39,45-46,49-54,57-60H,1-4H3/t15-,16-,34-,35-,36+,37+,38-,39-,45-,46-/m0/s1

InChI Key

UIUPYGWVOAFVLA-GWYUDNFRSA-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
Zingiber spectabile	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

Bi- and polyflavonoid skeleton
Flavonoid-3-o-glycoside
Flavonoid o-glycoside
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Chromone
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	2.97	ChemAxon
pKa (Strongest Acidic)	5.6	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	344.42 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	228.88 m³·mol⁻¹	ChemAxon
Polarizability	91.56 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28530687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70690358

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sivasothy Y, Hadi AH, Mohamad K, Leong KH, Ibrahim H, Sulaiman SF, Ooi KL, Awang K: Spectaflavoside A, a new potent iron chelating dimeric flavonol glycoside from the rhizomes of Zingiber spectabile Griff. Bioorg Med Chem Lett. 2012 Jun 1;22(11):3831-6. doi: 10.1016/j.bmcl.2012.02.064. Epub 2012 Mar 7. [PubMed:22546674 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate (NP0315339)

MOL for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D MOL for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D SDF for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D-SDF for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

PDB for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D PDB for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

SMILES for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

INCHI for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

Structure for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D Structure for NP0315339 ((2s,3r,4s,5r,6s)-6-[(3'-{[(2s,3r,4s,5r,6s)-5-(acetyloxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[6,8'-bichromene]-4,4'-diyl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate)