NP-MRD: Showing NP-Card for Broussonetine U (NP0025685)

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Record Information

Version

1.0

Created at

2021-06-19 17:44:48 UTC

Updated at

2021-06-29 23:50:47 UTC

NP-MRD ID

NP0025685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Broussonetine U

Provided By

JEOL Database JEOL Logo

Description

13-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyrrol-5-yl]-1-hydroxytridecan-5-one belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. Broussonetine U is found in Broussonetia kaziniki Sieb. and Broussonetia kazinoki SIEB. . It was first documented in 2001 (Tsukamoto, D., et al.). Based on a literature review very few articles have been published on 13-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyrrol-5-yl]-1-hydroxytridecan-5-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119443D          

 57 57  0  0  0  0            999 V2000
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   -0.3090   -3.4892    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6879   -4.1733    1.6111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2514   -3.3773    2.8421 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2022   -2.2222    3.1747 C   0  0  2  0  0  0  0  0  0  0  0  0
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 23 24  1  0  0  0  0
  2  3  1  0  0  0  0
 17 18  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119443D          

 57 57  0  0  0  0            999 V2000
   -0.3986   -2.2696    0.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3090   -3.4892    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2914   -1.6569   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736   -1.2482   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778   -5.1434    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657   -4.3644    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2177   -4.0545    3.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7684   -3.0103    2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902   -2.6355    3.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -1.5753    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -1.9706    5.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779   -0.5636    4.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154   -1.5069    4.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7923   -0.0429    5.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.6723    2.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0696    0.7643    2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    1.5851    3.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    0.0410    3.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    1.5649    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.3358    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    5.0344    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549    5.5174   -1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    4.2424   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356    5.3831    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850    3.5300   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    3.9939    1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    1.0854    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763    0.8280   -1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0  0  0  0
 16 15  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
 15 14  1  0  0  0  0
 11 10  1  0  0  0  0
 23 16  1  0  0  0  0
 10  9  1  0  0  0  0
 14 13  1  0  0  0  0
  9  8  1  0  0  0  0
 16 17  2  0  0  0  0
  8  2  1  0  0  0  0
 23 24  1  0  0  0  0
  2  3  1  0  0  0  0
 17 18  1  0  0  0  0
  3  4  1  0  0  0  0
 18 19  1  0  0  0  0
  4  5  1  0  0  0  0
 18 21  1  0  0  0  0
  5  6  1  0  0  0  0
 21 22  1  0  0  0  0
  6  7  1  0  0  0  0
 21 23  1  0  0  0  0
  2  1  2  0  0  0  0
 21 54  1  6  0  0  0
 23 56  1  1  0  0  0
 18 50  1  1  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 24 57  1  0  0  0  0
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 22 55  1  0  0  0  0
 20 53  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1=N[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H33NO5/c20-12-8-7-10-14(22)9-5-3-1-2-4-6-11-15-17(23)18(24)16(13-21)19-15/h16-18,20-21,23-24H,1-13H2/t16-,17-,18-/m0/s1

> <INCHI_KEY>
PRALTWWUFVAKLH-BZSNNMDCSA-N

> <FORMULA>
C18H33NO5

> <MOLECULAR_WEIGHT>
343.464

> <EXACT_MASS>
343.235873167

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
38.36917587756453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyrrol-5-yl]-1-hydroxytridecan-5-one

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.2800256216666668

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.121273764873195

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.776649006338538

> <JCHEM_PKA_STRONGEST_BASIC>
4.110703165640127

> <JCHEM_POLAR_SURFACE_AREA>
110.35000000000001

> <JCHEM_REFRACTIVITY>
92.36009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-[(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-4,5-dihydro-3H-pyrrol-2-yl]-1-hydroxytridecan-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 57  0  0  0  0  0  0  0  0999 V2000
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   -1.1448    3.1112    1.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244    1.9584   -0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1027    1.7718   -1.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -5.1070   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2725   -2.8510   -2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -4.3615   -2.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -2.6424   -3.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032   -3.9165   -2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -2.4494   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7630   -1.9706    5.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7923   -0.0429    5.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.6723    2.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0696    0.7643    2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    1.5851    3.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    0.0410    3.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    1.5649    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.3358    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    5.0344    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549    5.5174   -1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    4.2424   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356    5.3831    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850    3.5300   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    3.9939    1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    1.0854    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763    0.8280   -1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 16 15  1  0
 13 12  1  0
 12 11  1  0
 15 14  1  0
 11 10  1  0
 23 16  1  0
 10  9  1  0
 14 13  1  0
  9  8  1  0
 16 17  2  0
  8  2  1  0
 23 24  1  0
  2  3  1  0
 17 18  1  0
  3  4  1  0
 18 19  1  0
  4  5  1  0
 18 21  1  0
  5  6  1  0
 21 22  1  0
  6  7  1  0
 21 23  1  0
  2  1  2  0
 21 54  1  6
 23 56  1  1
 18 50  1  1
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 13 44  1  0
 13 45  1  0
 24 57  1  0
 19 51  1  0
 19 52  1  0
 22 55  1  0
 20 53  1  0
 12 42  1  0
 12 43  1  0
 11 40  1  0
 11 41  1  0
 10 38  1  0
 10 39  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  0
  8 35  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  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      -0.399  -2.270   0.157  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.309  -3.489   0.306  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.163  -4.392  -0.823  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.460  -3.648  -2.129  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.885  -3.088  -2.247  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.293  -2.035  -1.222  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.402  -0.927  -1.230  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.688  -4.173   1.611  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.251  -3.377   2.842  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.202  -2.222   3.175  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.741  -1.364   4.358  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.649  -0.729   4.230  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.869   0.027   2.918  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.229   0.728   2.892  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.637   1.180   1.491  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.756   2.274   0.955  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.952   3.521   1.281  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.907   4.275   0.522  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.582   4.956  -0.674  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.564   5.875  -0.191  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.163   3.254   0.120  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.145   3.111   1.157  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.624   1.958  -0.002  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.103   1.772  -1.321  0.00  0.00           O+0
HETATM   25  H   UNK     0      -0.648  -5.107  -1.007  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.044  -4.949  -0.488  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.273  -2.851  -2.303  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.330  -4.362  -2.953  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.973  -2.642  -3.246  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.603  -3.917  -2.208  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.339  -2.449  -0.210  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.291  -1.657  -1.464  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.574  -1.248  -0.801  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.178  -5.143   1.637  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.766  -4.364   1.608  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.218  -4.054   3.704  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.768  -3.010   2.685  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.190  -2.636   3.414  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.353  -1.575   2.305  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.763  -1.971   5.272  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.478  -0.564   4.504  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.415  -1.507   4.336  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.792  -0.043   5.074  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.816  -0.672   2.077  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.070   0.764   2.783  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.208   1.585   3.576  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.000   0.041   3.262  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.663   1.565   1.525  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.634   0.336   0.796  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.497   5.034   1.199  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.855   5.517  -1.268  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.091   4.242  -1.329  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.036   5.383   0.512  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.685   3.530  -0.802  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.515   3.994   1.331  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.052   1.085   0.322  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.376   0.828  -1.388  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    8    3    1                                                  
CONECT    3    2    4   25   26                                             
CONECT    4    3    5   27   28                                             
CONECT    5    4    6   29   30                                             
CONECT    6    5    7   31   32                                             
CONECT    7    6   33                                                       
CONECT    8    9    2   34   35                                             
CONECT    9   10    8   36   37                                             
CONECT   10   11    9   38   39                                             
CONECT   11   12   10   40   41                                             
CONECT   12   13   11   42   43                                             
CONECT   13   12   14   44   45                                             
CONECT   14   15   13   46   47                                             
CONECT   15   16   14   48   49                                             
CONECT   16   15   23   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21   50                                             
CONECT   19   20   18   51   52                                             
CONECT   20   19   53                                                       
CONECT   21   18   22   23   54                                             
CONECT   22   21   55                                                       
CONECT   23   16   24   21   56                                             
CONECT   24   23   57                                                       
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  114    0
END

RDKit          3D

57 57  0  0  0  0  0  0  0  0999 V2000
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   -0.3090   -3.4892    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4596   -3.6481   -2.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853   -3.0885   -2.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930   -2.0352   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.9266   -1.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2514   -3.3773    2.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -2.2222    3.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412   -1.3637    4.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6244    1.9584   -0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1027    1.7718   -1.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -5.1070   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -4.9490   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725   -2.8510   -2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -4.3615   -2.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -2.6424   -3.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032   -3.9165   -2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -2.4494   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.6569   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736   -1.2482   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778   -5.1434    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2177   -4.0545    3.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7684   -3.0103    2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902   -2.6355    3.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -1.5753    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -1.9706    5.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779   -0.5636    4.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154   -1.5069    4.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7923   -0.0429    5.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -0.6723    2.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0696    0.7643    2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    1.5851    3.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    0.0410    3.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    1.5649    1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.3358    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    5.0344    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549    5.5174   -1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    4.2424   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356    5.3831    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850    3.5300   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    3.9939    1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    1.0854    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763    0.8280   -1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 16 15  1  0
 13 12  1  0
 12 11  1  0
 15 14  1  0
 11 10  1  0
 23 16  1  0
 10  9  1  0
 14 13  1  0
  9  8  1  0
 16 17  2  0
  8  2  1  0
 23 24  1  0
  2  3  1  0
 17 18  1  0
  3  4  1  0
 18 19  1  0
  4  5  1  0
 18 21  1  0
  5  6  1  0
 21 22  1  0
  6  7  1  0
 21 23  1  0
  2  1  2  0
 21 54  1  6
 23 56  1  1
 18 50  1  1
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 13 44  1  0
 13 45  1  0
 24 57  1  0
 19 51  1  0
 19 52  1  0
 22 55  1  0
 20 53  1  0
 12 42  1  0
 12 43  1  0
 11 40  1  0
 11 41  1  0
 10 38  1  0
 10 39  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  0
  8 35  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₃NO₅

Average Mass

343.4640 Da

Monoisotopic Mass

343.23587 Da

IUPAC Name

13-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyrrol-5-yl]-1-hydroxytridecan-5-one

Traditional Name

13-[(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-4,5-dihydro-3H-pyrrol-2-yl]-1-hydroxytridecan-5-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1=N[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C18H33NO5/c20-12-8-7-10-14(22)9-5-3-1-2-4-6-11-15-17(23)18(24)16(13-21)19-15/h16-18,20-21,23-24H,1-13H2/t16-,17-,18-/m0/s1

InChI Key

PRALTWWUFVAKLH-BZSNNMDCSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
1,2-diol
Ketimine
Ketone
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Imine
Carbonyl group
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	1.59	ALOGPS
logP	1.28	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	4.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	110.35 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	92.36 m³·mol⁻¹	ChemAxon
Polarizability	38.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

8696740

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10521342

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tsukamoto, D., et al. (2001). Tsukamoto, D., et al, Chem. Pharm. Bull. 49, 492 (2001). Chem. Pharm. Bull..

Showing NP-Card for Broussonetine U (NP0025685)

MOL for NP0025685 (Broussonetine U)

3D MOL for NP0025685 (Broussonetine U)

3D SDF for NP0025685 (Broussonetine U)

3D-SDF for NP0025685 (Broussonetine U)

PDB for NP0025685 (Broussonetine U)

3D PDB for NP0025685 (Broussonetine U)

SMILES for NP0025685 (Broussonetine U)

INCHI for NP0025685 (Broussonetine U)

Structure for NP0025685 (Broussonetine U)

3D Structure for NP0025685 (Broussonetine U)