NP-MRD: Showing NP-Card for Broussonetine T (NP0025684)

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Record Information

Version

1.0

Created at

2021-06-19 17:44:46 UTC

Updated at

2021-06-29 23:50:47 UTC

NP-MRD ID

NP0025684

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Broussonetine T

Provided By

JEOL Database JEOL Logo

Description

(9S,13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,9,13-trihydroxytridecan-4-one belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Broussonetine T is found in Broussonetia kaziniki Sieb., Broussonetia kazinoki SIEB. and Broussonetia papyrifera. It was first documented in 2021 (PMID: 34352962). Based on a literature review a significant number of articles have been published on (9S,13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,9,13-trihydroxytridecan-4-one (PMID: 34352961) (PMID: 34352960) (PMID: 34352959) (PMID: 34352958) (PMID: 34352957) (PMID: 34352956).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119443D          

 61 61  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119443D          

 61 61  0  0  0  0            999 V2000
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   -1.3941    1.0544    0.5255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1660   -0.3382    0.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4270   -1.4046   -4.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7468   -0.4330   -4.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    1.0604   -4.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    1.1088   -2.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328   -0.4436   -2.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865   -0.5418   -4.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5014    1.8032   -4.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176    2.1359   -2.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    2.0926   -3.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -0.6992   -3.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284    0.6883   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714   -0.2508   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7210    2.7565   -1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4667    2.8946    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1994    3.9982    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4815    4.9279    2.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0892    0.8561    1.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548    0.3217   -0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2739    1.2812   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -0.7952    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0  0  0  0
 16 15  1  0  0  0  0
 14 13  1  0  0  0  0
 25 18  1  0  0  0  0
 13 11  1  0  0  0  0
 15 14  1  0  0  0  0
 11 10  1  0  0  0  0
 18 19  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  1  0  0  0  0
  9  8  1  0  0  0  0
 19 20  1  0  0  0  0
  8  7  1  0  0  0  0
 20 21  1  0  0  0  0
  7  2  1  0  0  0  0
 20 23  1  0  0  0  0
  2  3  1  0  0  0  0
 23 24  1  0  0  0  0
  3  4  1  0  0  0  0
 23 25  1  0  0  0  0
  4  5  1  0  0  0  0
 16 17  1  0  0  0  0
  5  6  1  0  0  0  0
 18 16  1  0  0  0  0
  2  1  2  0  0  0  0
 18 52  1  1  0  0  0
 11 12  1  0  0  0  0
 23 58  1  1  0  0  0
 25 60  1  6  0  0  0
 19 53  1  0  0  0  0
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 15 48  1  0  0  0  0
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 14 46  1  0  0  0  0
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 26 61  1  0  0  0  0
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 13 44  1  0  0  0  0
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 11 42  1  6  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
  6 33  1  0  0  0  0
 12 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025684

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@@]1([H])N([H])[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H35NO7/c20-10-4-8-13(23)6-2-1-5-12(22)7-3-9-15(24)16-18(26)17(25)14(11-21)19-16/h12,14-22,24-26H,1-11H2/t12-,14+,15+,16+,17+,18+/m0/s1

> <INCHI_KEY>
IRZPHQYUBDNBAV-SBYMSKKQSA-N

> <FORMULA>
C18H35NO7

> <MOLECULAR_WEIGHT>
377.478

> <EXACT_MASS>
377.241352471

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
40.35046349389498

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,9,13-trihydroxytridecan-4-one

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-1.5035739823333336

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.227025846561194

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.160764391266216

> <JCHEM_PKA_STRONGEST_BASIC>
9.077124443229499

> <JCHEM_POLAR_SURFACE_AREA>
150.48

> <JCHEM_REFRACTIVITY>
95.7668

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,9,13-trihydroxytridecan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 61  0  0  0  0  0  0  0  0999 V2000
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    1.5476    1.3803   -3.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259    1.1582   -3.2437 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.7210    2.7565   -1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6826   -0.7952    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0
 16 15  1  0
 14 13  1  0
 25 18  1  0
 13 11  1  0
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 18 19  1  0
 10  9  1  0
 25 26  1  0
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  7  2  1  0
 20 23  1  0
  2  3  1  0
 23 24  1  0
  3  4  1  0
 23 25  1  0
  4  5  1  0
 16 17  1  0
  5  6  1  0
 18 16  1  0
  2  1  2  0
 18 52  1  1
 11 12  1  0
 23 58  1  1
 25 60  1  6
 19 53  1  0
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 21 55  1  0
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 13 44  1  0
 13 45  1  0
 11 42  1  6
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  9 38  1  0
  9 39  1  0
  8 36  1  0
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  3 27  1  0
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  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
 12 43  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.343  -1.128  -1.540  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.727  -1.536  -2.530  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.953  -2.842  -2.516  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.330  -3.112  -1.148  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.580  -4.332  -1.166  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.661  -4.104  -2.060  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.716  -0.749  -3.828  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.803   0.471  -3.751  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.681   0.115  -3.594  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.548   1.380  -3.595  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.026   1.158  -3.244  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.581   0.174  -4.119  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.336   0.762  -1.789  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.836   1.764  -0.740  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.538   1.292  -0.074  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.792   2.410   0.664  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.400   3.408  -0.287  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.468   1.903   1.411  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.279   3.059   1.913  0.00  0.00           N+0
HETATM   20  C   UNK     0      -2.624   2.913   1.277  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.738   3.478   2.165  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.454   4.838   2.497  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.796   1.428   0.983  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.758   1.190  -0.038  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.394   1.054   0.526  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.166  -0.338   0.725  0.00  0.00           O+0
HETATM   27  H   UNK     0      -0.166  -2.783  -3.276  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.638  -3.647  -2.802  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.255  -2.235  -0.845  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.117  -3.255  -0.400  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.036  -5.224  -1.490  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.989  -4.511  -0.166  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.249  -4.877  -1.996  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.427  -1.405  -4.656  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.747  -0.433  -4.026  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.936   1.060  -4.666  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.113   1.109  -2.915  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.833  -0.444  -2.666  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.987  -0.542  -4.418  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.501   1.803  -4.608  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.118   2.136  -2.929  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.559   2.093  -3.458  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.274  -0.699  -3.821  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.428   0.688  -1.701  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.971  -0.251  -1.577  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.596   1.868   0.044  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.721   2.757  -1.189  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.768   0.475   0.621  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.887   0.882  -0.848  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.467   2.895   1.380  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.199   3.998   0.213  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.136   1.306   2.271  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.390   2.922   2.923  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.609   3.491   0.343  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.825   2.917   3.101  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.704   3.445   1.653  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.482   4.928   2.477  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.089   0.856   1.871  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.555   0.322  -0.443  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.274   1.281  -0.540  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.683  -0.795   0.026  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    7    3    1                                                  
CONECT    3    2    4   27   28                                             
CONECT    4    3    5   29   30                                             
CONECT    5    4    6   31   32                                             
CONECT    6    5   33                                                       
CONECT    7    8    2   34   35                                             
CONECT    8    9    7   36   37                                             
CONECT    9   10    8   38   39                                             
CONECT   10   11    9   40   41                                             
CONECT   11   13   10   12   42                                             
CONECT   12   11   43                                                       
CONECT   13   14   11   44   45                                             
CONECT   14   13   15   46   47                                             
CONECT   15   16   14   48   49                                             
CONECT   16   15   17   18   50                                             
CONECT   17   16   51                                                       
CONECT   18   25   19   16   52                                             
CONECT   19   18   20   53                                                  
CONECT   20   19   21   23   54                                             
CONECT   21   22   20   55   56                                             
CONECT   22   21   57                                                       
CONECT   23   20   24   25   58                                             
CONECT   24   23   59                                                       
CONECT   25   18   26   23   60                                             
CONECT   26   25   61                                                       
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  122    0
END

RDKit          3D

61 61  0  0  0  0  0  0  0  0999 V2000
   -2.3430   -1.1277   -1.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7274   -1.5358   -2.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526   -2.8418   -2.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -3.1125   -1.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796   -4.3321   -1.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605   -4.1035   -2.0602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.7493   -3.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031    0.4708   -3.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    0.1145   -3.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476    1.3803   -3.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259    1.1582   -3.2437 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5813    0.1744   -4.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358    0.7620   -1.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8356    1.7641   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5380    1.2918   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921    2.4097    0.6638 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4003    3.4079   -0.2868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4680    1.9026    1.4111 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2794    3.0594    1.9132 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6239    2.9130    1.2770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7380    3.4780    2.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4536    4.8381    2.4968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7955    1.4282    0.9826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7584    1.1896   -0.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3941    1.0544    0.5255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1660   -0.3382    0.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663   -2.7834   -3.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6379   -3.6467   -2.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2550   -2.2352   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1173   -3.2550   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355   -5.2245   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886   -4.5109   -0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2489   -4.8767   -1.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -1.4046   -4.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7468   -0.4330   -4.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    1.0604   -4.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    1.1088   -2.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328   -0.4436   -2.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865   -0.5418   -4.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5014    1.8032   -4.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176    2.1359   -2.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590    2.0926   -3.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2738   -0.6992   -3.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284    0.6883   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714   -0.2508   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5962    1.8679    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210    2.7565   -1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7683    0.4751    0.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873    0.8816   -0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667    2.8946    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1994    3.9982    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359    1.3064    2.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    2.9223    2.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6091    3.4908    0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    2.9171    3.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7044    3.4452    1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815    4.9279    2.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0892    0.8561    1.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548    0.3217   -0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2739    1.2812   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -0.7952    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0
 16 15  1  0
 14 13  1  0
 25 18  1  0
 13 11  1  0
 15 14  1  0
 11 10  1  0
 18 19  1  0
 10  9  1  0
 25 26  1  0
  9  8  1  0
 19 20  1  0
  8  7  1  0
 20 21  1  0
  7  2  1  0
 20 23  1  0
  2  3  1  0
 23 24  1  0
  3  4  1  0
 23 25  1  0
  4  5  1  0
 16 17  1  0
  5  6  1  0
 18 16  1  0
  2  1  2  0
 18 52  1  1
 11 12  1  0
 23 58  1  1
 25 60  1  6
 19 53  1  0
 20 54  1  6
 16 50  1  1
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 26 61  1  0
 21 55  1  0
 21 56  1  0
 24 59  1  0
 17 51  1  0
 22 57  1  0
 13 44  1  0
 13 45  1  0
 11 42  1  6
 10 40  1  0
 10 41  1  0
  9 38  1  0
  9 39  1  0
  8 36  1  0
  8 37  1  0
  7 34  1  0
  7 35  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
 12 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₅NO₇

Average Mass

377.4780 Da

Monoisotopic Mass

377.24135 Da

IUPAC Name

(9S,13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,9,13-trihydroxytridecan-4-one

Traditional Name

(9S,13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,9,13-trihydroxytridecan-4-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C([H])([H])C([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@@]1([H])N([H])[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C18H35NO7/c20-10-4-8-13(23)6-2-1-5-12(22)7-3-9-15(24)16-18(26)17(25)14(11-21)19-16/h12,14-22,24-26H,1-11H2/t12-,14+,15+,16+,17+,18+/m0/s1

InChI Key

IRZPHQYUBDNBAV-SBYMSKKQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Broussonetia kaziniki Sieb.	JEOL database	Tsukamoto, D., et al, Chem. Pharm. Bull. 49, 492 (2001)
Broussonetia kazinoki SIEB.	Plant	KNApSAcK
Broussonetia papyrifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Not Available

Direct Parent

Pyrrolidines

Alternative Parents

Substituents

Pyrrolidine
1,2-aminoalcohol
1,2-diol
Ketone
Secondary alcohol
Secondary aliphatic amine
Polyol
Azacycle
Secondary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Amine
Primary alcohol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.33	ALOGPS
logP	-1.5	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	150.48 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	95.77 m³·mol⁻¹	ChemAxon
Polarizability	40.35 Å³	ChemAxon
Number of Rings	1	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

8961146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10785833

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Velazquez-Mujica J, Losco L, Aksoyler D, Chen HC: Perforator-to-perforator anastomosis as a salvage procedure during harvest of a perforator flap. Arch Plast Surg. 2021 Jul;48(4):467-469. doi: 10.5999/aps.2020.02194. Epub 2021 Jul 15. [PubMed:34352962 ]
Santamaria E, Nahas-Combina L, Altamirano-Arcos C, Vargas-Flores E: Seven steps to deliver a low-cost, efficient, and high-impact online plastic surgery course during COVID-19 confinement: master series microsurgery for residents' experience. Arch Plast Surg. 2021 Jul;48(4):462-466. doi: 10.5999/aps.2021.00360. Epub 2021 Jul 15. [PubMed:34352961 ]
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Showing NP-Card for Broussonetine T (NP0025684)

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