NP-MRD: Showing NP-Card for (1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione (NP0293583)

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Record Information

Version

2.0

Created at

2022-09-10 01:39:50 UTC

Updated at

2022-09-10 01:39:50 UTC

NP-MRD ID

NP0293583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione

Description

(1R,3S,4S,5S,6R,10S,11S,12S,13R,17R,18S,19S,20R)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]Docosane-9,14-dione belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms. (1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione is found in Bidens parviflora. Based on a literature review very few articles have been published on (1R,3S,4S,5S,6R,10S,11S,12S,13R,17R,18S,19S,20R)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]Docosane-9,14-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102203392D          

 45 50  0  0  1  0            999 V2000
   -0.1825    1.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284    0.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441    0.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503    0.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1529    1.2290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8655    0.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5818    1.2224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1975    1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9809    1.5129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2944    0.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2906   -0.0183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5743   -0.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705   -1.2525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8542   -1.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416   -1.2460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215   -2.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 40 41  1  6  0  0  0
  7 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
  5 44  1  0  0  0  0
 44 45  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102203392D          

 45 50  0  0  1  0            999 V2000
   -0.1825    1.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1529    1.2290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8655    0.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5818    1.2224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.2944    0.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2906   -0.0183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5743   -0.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705   -1.2525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8542   -1.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416   -1.2460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215   -2.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127   -1.2395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6806   -0.4151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1438   -0.4471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7493    0.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373   -0.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    0.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9605    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661    1.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    0.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -1.2715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6720   -1.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277   -2.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879   -3.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925   -3.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528   -3.6938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766   -1.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2831   -1.6683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2793   -2.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994   -1.2591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7120   -1.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032   -0.4341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7196   -0.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364    2.0087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6890    2.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114    2.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9296    2.6821    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 16  1  6  0  0  0
 18 19  1  0  0  0  0
 19  2  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 20 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 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
 29 35  1  0  0  0  0
 13 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  6  0  0  0
  7 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
  5 44  1  0  0  0  0
 44 45  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0293583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@]12O[C@H](COC(=O)[C@H]3[C@H]([C@@H]([C@H]3C(=O)OC[C@H]3O[C@H](O1)[C@H](O)[C@@H](O)[C@@H]3O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)[C@@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O15/c31-11-30-26(38)23(35)17(44-30)10-42-28(40)21-19(13-3-7-15(33)8-4-13)18(12-1-5-14(32)6-2-12)20(21)27(39)41-9-16-22(34)24(36)25(37)29(43-16)45-30/h1-8,16-26,29,31-38H,9-11H2/t16-,17-,18+,19+,20-,21+,22-,23-,24+,25-,26+,29-,30+/m1/s1

> <INCHI_KEY>
LXZBDLMRSNTLOR-POUUPCGESA-N

> <FORMULA>
C30H34O15

> <MOLECULAR_WEIGHT>
634.587

> <EXACT_MASS>
634.189770395

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
61.593461120014396

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4S,5S,6R,10S,11S,12S,13R,17R,18S,19S,20R)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1^{3,6}.0^{10,13}]docosane-9,14-dione

> <JCHEM_LOGP>
-0.741613532999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.798966570479573

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.198870653156764

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4558263002974163

> <JCHEM_POLAR_SURFACE_AREA>
242.12999999999997

> <JCHEM_REFRACTIVITY>
145.92250000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4S,5S,6R,10S,11S,12S,13R,17R,18S,19S,20R)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1^{3,6}.0^{10,13}]docosane-9,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.341   1.946   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.240   0.519   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.016   1.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.521   1.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.019   2.294   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.349   1.518   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.686   2.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.835   3.307   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.298   2.824   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.016   1.506   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.009  -0.034   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.672  -0.798   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.665  -2.338   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.328  -3.102   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.998  -2.326   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.660  -3.090   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.653  -4.630   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.330  -2.314   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.270  -0.775   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.268  -0.835   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.399   0.211   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.870  -0.245   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.000   0.801   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.660   2.303   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.790   3.349   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.189   2.759   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.058   1.713   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.209  -2.373   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.254  -3.504   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.798  -4.975   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.844  -6.105   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.346  -5.765   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.392  -6.895   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.802  -4.294   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.756  -3.163   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.995  -3.114   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.988  -4.654   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.332  -2.350   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.662  -3.126   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.339  -0.810   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.677  -0.046   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.041   3.749   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.886   5.037   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.501   3.757   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       3.602   5.007   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   44                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10   42                                             
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18    2   20                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   20   18   29                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
CONECT   36   13   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   11   41                                                  
CONECT   41   40                                                            
CONECT   42    7   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42    5   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₁₅

Average Mass

634.5870 Da

Monoisotopic Mass

634.18977 Da

IUPAC Name

(1R,3S,4S,5S,6R,10S,11S,12S,13R,17R,18S,19S,20R)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1^{3,6}.0^{10,13}]docosane-9,14-dione

Traditional Name

(1R,3S,4S,5S,6R,10S,11S,12S,13R,17R,18S,19S,20R)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1^{3,6}.0^{10,13}]docosane-9,14-dione

CAS Registry Number

Not Available

SMILES

OC[C@]12O[C@H](COC(=O)[C@H]3[C@H]([C@@H]([C@H]3C(=O)OC[C@H]3O[C@H](O1)[C@H](O)[C@@H](O)[C@@H]3O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)[C@@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C30H34O15/c31-11-30-26(38)23(35)17(44-30)10-42-28(40)21-19(13-3-7-15(33)8-4-13)18(12-1-5-14(32)6-2-12)20(21)27(39)41-9-16-22(34)24(36)25(37)29(43-16)45-30/h1-8,16-26,29,31-38H,9-11H2/t16-,17-,18+,19+,20-,21+,22-,23-,24+,25-,26+,29-,30+/m1/s1

InChI Key

LXZBDLMRSNTLOR-POUUPCGESA-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
Bidens parviflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Cyclobutane lignans

Sub Class

Not Available

Direct Parent

Cyclobutane lignans

Alternative Parents

Substituents

Cyclobutane lignan skeleton
Lignan lactone
Stilbene
Macrolide
Disaccharide
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Oxane
Benzenoid
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	-0.74	ChemAxon
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	242.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	145.92 m³·mol⁻¹	ChemAxon
Polarizability	61.59 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	No	ChemAxon

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PubChem Compound

162898780

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References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione (NP0293583)

MOL for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

3D MOL for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

3D SDF for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

3D-SDF for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

PDB for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

3D PDB for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

SMILES for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

INCHI for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

Structure for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)

3D Structure for NP0293583 ((1r,3s,4s,5s,6r,10s,11s,12s,13r,17r,18s,19s,20r)-4,5,18,19,20-pentahydroxy-3-(hydroxymethyl)-11,12-bis(4-hydroxyphenyl)-2,8,15,21,22-pentaoxatetracyclo[15.3.1.1³,⁶.0¹⁰,¹³]docosane-9,14-dione)