NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol (NP0224409)

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Record Information

Version

2.0

Created at

2022-09-06 02:45:37 UTC

Updated at

2022-09-06 02:45:37 UTC

NP-MRD ID

NP0224409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol

Description

(-)-Syringaresnol-4-O-|A-D-apiofuranosyl-(1 inverted exclamation marku2)-|A-D-glucopyranoside belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol is found in Albizia julibrissin. Based on a literature review very few articles have been published on (-)-Syringaresnol-4-O-|A-D-apiofuranosyl-(1 inverted exclamation marku2)-|A-D-glucopyranoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204452D          

 50 55  0  0  1  0            999 V2000
    1.4012    2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    2.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960   -4.6449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9480   -4.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -4.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3070   -3.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140   -3.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099   -4.9879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8169   -5.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4579   -5.6010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7128   -6.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -5.4295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0989   -6.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -6.8272    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1384   -7.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384   -7.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -8.1621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6894   -8.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393   -8.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393   -9.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8689   -7.4947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0439   -7.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788    2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  6  0  0  0
 37 38  1  0  0  0  0
 35 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 19 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 44  2  0  0  0  0
 14 44  1  0  0  0  0
  5 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 46 49  2  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END


  Mrv1652309062204452D          

 50 55  0  0  1  0            999 V2000
    1.4012    2.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    2.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960   -4.6449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9480   -4.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -4.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3070   -3.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140   -3.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099   -4.9879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8169   -5.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4579   -5.6010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7128   -6.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -5.4295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0989   -6.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -6.8272    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1384   -7.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384   -7.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -8.1621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6894   -8.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393   -8.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393   -9.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8689   -7.4947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0439   -7.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788    2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  6  0  0  0
 37 38  1  0  0  0  0
 35 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 19 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 44  2  0  0  0  0
 14 44  1  0  0  0  0
  5 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 46 49  2  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2C1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O17/c1-41-18-5-14(6-19(42-2)23(18)36)26-16-10-46-27(17(16)11-45-26)15-7-20(43-3)28(21(8-15)44-4)49-31-29(25(38)24(37)22(9-34)48-31)50-32-30(39)33(40,12-35)13-47-32/h5-8,16-17,22,24-27,29-32,34-40H,9-13H2,1-4H3/t16-,17-,22-,24-,25+,26+,27+,29-,30+,31+,32+,33-/m1/s1

> <INCHI_KEY>
BUBVKRMIMSPLND-XSTKEGOHSA-N

> <FORMULA>
C33H44O17

> <MOLECULAR_WEIGHT>
712.698

> <EXACT_MASS>
712.257849957

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
70.66192838047404

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-6-{4-[(1R,3aS,4R,6aS)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol

> <JCHEM_LOGP>
-1.5821501373333324

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.808724399925788

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.301642003945357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810925917908886

> <JCHEM_POLAR_SURFACE_AREA>
233.90999999999997

> <JCHEM_REFRACTIVITY>
166.8412

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-6-{4-[(1R,3aS,4R,6aS)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol

> <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  C   UNK     0       2.615   4.898   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.079   4.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.555   2.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.476   1.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.894  -6.061   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.924  -4.917   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.339  -8.670   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.370  -7.526   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.876  -7.846   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.906  -6.702   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.413  -7.022   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.352  -9.311   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.858  -9.631   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.321 -10.455   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.797 -11.920   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.815 -10.135   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.785 -11.280   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.260 -12.744   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.725 -13.220   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.725 -14.760   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.260 -15.236   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.887 -16.643   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.927 -16.006   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.927 -17.546   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.355 -13.990   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.815 -13.990   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.820  -7.710   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.314  -7.390   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.982   1.785   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -3.964   3.570   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -4.440   5.034   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -1.428   4.394   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.904   5.859   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   49                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   45                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   44                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   41                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   39                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39   35   32   40                                                  
CONECT   40   39                                                            
CONECT   41   19   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   14                                                       
CONECT   45    5   46                                                       
CONECT   46   45   47   49                                                  
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   46    3   50                                                  
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₄O₁₇

Average Mass

712.6980 Da

Monoisotopic Mass

712.25785 Da

IUPAC Name

(2R,3S,4S,5R,6S)-6-{4-[(1R,3aS,4R,6aS)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2C1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)C(OC)=C1

InChI Identifier

InChI=1S/C33H44O17/c1-41-18-5-14(6-19(42-2)23(18)36)26-16-10-46-27(17(16)11-45-26)15-7-20(43-3)28(21(8-15)44-4)49-31-29(25(38)24(37)22(9-34)48-31)50-32-30(39)33(40,12-35)13-47-32/h5-8,16-17,22,24-27,29-32,34-40H,9-13H2,1-4H3/t16-,17-,22-,24-,25+,26+,27+,29-,30+,31+,32+,33-/m1/s1

InChI Key

BUBVKRMIMSPLND-XSTKEGOHSA-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
Albizia julibrissin	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Furanoid lignan
Furofuran lignan skeleton
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Fatty acyl glycoside
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Disaccharide
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Phenol ether
Furofuran
Phenoxy compound
Methoxybenzene
Anisole
Phenol
Alkyl aryl ether
Fatty acyl
Oxane
Benzenoid
Monocyclic benzene moiety
Oxolane
Tertiary alcohol
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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	-1.6	ChemAxon
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	233.91 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	166.84 m³·mol⁻¹	ChemAxon
Polarizability	70.66 Å³	ChemAxon
Number of Rings	6	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

C00000724

Chemspider ID

57620518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101604422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol (NP0224409)

MOL for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

3D MOL for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

3D SDF for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

3D-SDF for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

PDB for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

3D PDB for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

SMILES for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

INCHI for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

Structure for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)

3D Structure for NP0224409 ((2r,3s,4s,5r,6s)-6-{4-[(1r,3as,4r,6as)-4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol)