NP-MRD: Showing NP-Card for Broussonetine R (NP0025682)

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Record Information

Version

1.0

Created at

2021-06-19 17:44:41 UTC

Updated at

2021-06-29 23:50:47 UTC

NP-MRD ID

NP0025682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Broussonetine R

Provided By

JEOL Database JEOL Logo

Description

Broussonetine R is found in Broussonetia kaziniki Sieb., Broussonetia kazinoki, Broussonetia kazinoki SIEB. and Broussonetia papyrifera. It was first documented in 2013 (PMID: 23829312). Based on a literature review very few articles have been published on Broussonetine R (PMID: 31390139).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119443D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192119443D          

 56 57  0  0  0  0            999 V2000
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   -2.5048    2.8470   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9420    2.0625   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370    1.1507    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894   -2.4399    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.1287    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -3.7410    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -3.1483    0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271   -1.8709    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -3.9729   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -0.2492   -0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -1.3266   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -0.8247   -4.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.1804   -3.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    0.9292   -4.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274    1.4441   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -1.4352   -4.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.1527   -2.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -2.4581   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8675   -0.2256   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
 22 24  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
  6  7  1  0  0  0  0
 12  2  1  0  0  0  0
  7  8  1  0  0  0  0
 12  6  2  0  0  0  0
  8  9  1  0  0  0  0
  2  3  1  0  0  0  0
  9 10  1  0  0  0  0
  3  4  1  0  0  0  0
 10 11  1  0  0  0  0
 24 17  1  0  0  0  0
 24 25  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 18 19  1  0  0  0  0
 22 23  1  0  0  0  0
 19 22  1  0  0  0  0
 15 16  1  0  0  0  0
  4  5  1  0  0  0  0
 17 47  1  1  0  0  0
 17 15  1  0  0  0  0
 20 21  1  0  0  0  0
  5  6  1  0  0  0  0
  2  1  2  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
 22 53  1  6  0  0  0
 24 55  1  1  0  0  0
 18 48  1  0  0  0  0
 19 49  1  6  0  0  0
 15 45  1  1  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 11 40  1  0  0  0  0
 25 56  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 23 54  1  0  0  0  0
 16 46  1  0  0  0  0
 21 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C1=C(C(=O)C([H])([H])C([H])([H])C1([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/C18H31NO6/c20-9-2-1-4-11-5-3-6-14(22)12(11)7-8-15(23)16-18(25)17(24)13(10-21)19-16/h13,15-21,23-25H,1-10H2/t13-,15-,16-,17-,18-/m1/s1

> <INCHI_KEY>
IDNFDNMPJCCARF-JVNHZCFISA-N

> <FORMULA>
C18H31NO6

> <MOLECULAR_WEIGHT>
357.447

> <EXACT_MASS>
357.215137722

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
37.5939304798456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3R)-3-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3-hydroxypropyl]-3-(4-hydroxybutyl)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
-0.39

> <JCHEM_LOGP>
-0.8329834373333335

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.231916822693602

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.161112935596474

> <JCHEM_PKA_STRONGEST_BASIC>
8.976825647554593

> <JCHEM_POLAR_SURFACE_AREA>
130.25

> <JCHEM_REFRACTIVITY>
92.82550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3R)-3-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3-hydroxypropyl]-3-(4-hydroxybutyl)cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    1.3655   -3.3354    3.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4029   -2.1219    3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870   -1.5536    4.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7773   -0.1425    3.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.7305    3.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    0.1262    2.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5779    1.1388    2.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609    2.1172    1.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    2.9111    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    2.2247   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3194    0.9610   -0.2076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207   -1.1970    2.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.8688    1.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932   -2.8113    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -2.2290   -0.3020 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5163   -3.2868   -1.1249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131   -1.0786   -1.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7053   -0.5897   -2.0056 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.5638   -3.4416 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8572    0.8570   -3.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948    1.7796   -3.4801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2031   -1.6184   -3.5837 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7910   -2.9179   -3.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608   -1.5126   -2.2643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5839   -0.5228   -2.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -2.1862    4.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314   -1.5897    5.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -0.1467    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616    0.2723    4.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    1.7038    3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    0.9076    4.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    0.6444    2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    1.7123    3.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5470    1.6023    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    2.8382    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887    3.8868    0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927    3.0988    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    2.8470   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9420    2.0625   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370    1.1507    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894   -2.4399    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.1287    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -3.7410    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -3.1483    0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271   -1.8709    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -3.9729   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -0.2492   -0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -1.3266   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -0.8247   -4.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.1804   -3.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    0.9292   -4.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274    1.4441   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -1.4352   -4.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.1527   -2.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -2.4581   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8675   -0.2256   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 22 24  1  0
 14 13  1  0
 13 12  1  0
  6  7  1  0
 12  2  1  0
  7  8  1  0
 12  6  2  0
  8  9  1  0
  2  3  1  0
  9 10  1  0
  3  4  1  0
 10 11  1  0
 24 17  1  0
 24 25  1  0
 17 18  1  0
 19 20  1  0
 18 19  1  0
 22 23  1  0
 19 22  1  0
 15 16  1  0
  4  5  1  0
 17 47  1  1
 17 15  1  0
 20 21  1  0
  5  6  1  0
  2  1  2  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
 22 53  1  6
 24 55  1  1
 18 48  1  0
 19 49  1  6
 15 45  1  1
 14 43  1  0
 14 44  1  0
 13 41  1  0
 13 42  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 25 56  1  0
 20 50  1  0
 20 51  1  0
 23 54  1  0
 16 46  1  0
 21 52  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       1.365  -3.335   3.093  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.403  -2.122   3.293  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.387  -1.554   4.287  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.777  -0.143   3.912  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.539   0.731   3.799  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.467   0.126   2.911  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.578   1.139   2.465  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.061   2.117   1.403  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.186   2.911   0.725  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.740   2.225  -0.520  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.319   0.961  -0.208  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.421  -1.197   2.612  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.608  -1.869   1.716  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.093  -2.811   0.615  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.988  -2.229  -0.302  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.516  -3.287  -1.125  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.513  -1.079  -1.233  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.705  -0.590  -2.006  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.298  -0.564  -3.442  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.857   0.857  -3.828  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.895   1.780  -3.480  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.203  -1.618  -3.584  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.791  -2.918  -3.729  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.561  -1.513  -2.264  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.584  -0.523  -2.410  0.00  0.00           O+0
HETATM   26  H   UNK     0       3.281  -2.186   4.293  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.931  -1.590   5.282  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.312  -0.147   2.953  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.462   0.272   4.660  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.856   1.704   3.410  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.112   0.908   4.794  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.490   0.644   2.126  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.899   1.712   3.345  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.547   1.602   0.651  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.605   2.838   1.894  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.789   3.887   0.420  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.993   3.099   1.443  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.505   2.847  -0.995  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.942   2.063  -1.250  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.137   1.151   0.290  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.289  -2.440   2.360  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.234  -1.129   1.214  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.280  -3.741   1.059  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.951  -3.148   0.022  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.827  -1.871   0.306  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.850  -3.973  -0.514  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.150  -0.249  -0.623  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.418  -1.327  -1.935  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.183  -0.825  -4.036  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.049   1.180  -3.313  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.683   0.929  -4.906  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.227   1.444  -2.622  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.430  -1.435  -4.457  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.200  -3.153  -2.867  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.048  -2.458  -2.014  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.867  -0.226  -1.518  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   12    3    1                                                  
CONECT    3    2    4   26   27                                             
CONECT    4    3    5   28   29                                             
CONECT    5    4    6   30   31                                             
CONECT    6    7   12    5                                                  
CONECT    7    6    8   32   33                                             
CONECT    8    7    9   34   35                                             
CONECT    9    8   10   36   37                                             
CONECT   10    9   11   38   39                                             
CONECT   11   10   40                                                       
CONECT   12   13    2    6                                                  
CONECT   13   14   12   41   42                                             
CONECT   14   15   13   43   44                                             
CONECT   15   14   16   17   45                                             
CONECT   16   15   46                                                       
CONECT   17   24   18   47   15                                             
CONECT   18   17   19   48                                                  
CONECT   19   20   18   22   49                                             
CONECT   20   19   21   50   51                                             
CONECT   21   20   52                                                       
CONECT   22   24   23   19   53                                             
CONECT   23   22   54                                                       
CONECT   24   22   17   25   55                                             
CONECT   25   24   56                                                       
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    7                                                            
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   13                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

RDKit          3D

56 57  0  0  0  0  0  0  0  0999 V2000
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    1.4029   -2.1219    3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4665    0.1262    2.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7910   -2.9179   -3.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608   -1.5126   -2.2643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5839   -0.5228   -2.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -2.1862    4.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314   -1.5897    5.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -0.1467    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616    0.2723    4.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    1.7038    3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    0.9076    4.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    0.6444    2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5470    1.6023    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    2.8382    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9927    3.0988    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    2.8470   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9420    2.0625   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370    1.1507    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894   -2.4399    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.1287    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -3.7410    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9513   -3.1483    0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271   -1.8709    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -3.9729   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501   -0.2492   -0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175   -1.3266   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -0.8247   -4.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    1.1804   -3.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    0.9292   -4.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274    1.4441   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -1.4352   -4.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.1527   -2.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -2.4581   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8675   -0.2256   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 22 24  1  0
 14 13  1  0
 13 12  1  0
  6  7  1  0
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  7  8  1  0
 12  6  2  0
  8  9  1  0
  2  3  1  0
  9 10  1  0
  3  4  1  0
 10 11  1  0
 24 17  1  0
 24 25  1  0
 17 18  1  0
 19 20  1  0
 18 19  1  0
 22 23  1  0
 19 22  1  0
 15 16  1  0
  4  5  1  0
 17 47  1  1
 17 15  1  0
 20 21  1  0
  5  6  1  0
  2  1  2  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
 22 53  1  6
 24 55  1  1
 18 48  1  0
 19 49  1  6
 15 45  1  1
 14 43  1  0
 14 44  1  0
 13 41  1  0
 13 42  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
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 11 40  1  0
 25 56  1  0
 20 50  1  0
 20 51  1  0
 23 54  1  0
 16 46  1  0
 21 52  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₁NO₆

Average Mass

357.4470 Da

Monoisotopic Mass

357.21514 Da

IUPAC Name

2-[(3R)-3-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3-hydroxypropyl]-3-(4-hydroxybutyl)cyclohex-2-en-1-one

Traditional Name

2-[(3R)-3-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3-hydroxypropyl]-3-(4-hydroxybutyl)cyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C1=C(C(=O)C([H])([H])C([H])([H])C1([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/C18H31NO6/c20-9-2-1-4-11-5-3-6-14(22)12(11)7-8-15(23)16-18(25)17(24)13(10-21)19-16/h13,15-21,23-25H,1-10H2/t13-,15-,16-,17-,18-/m1/s1

InChI Key

IDNFDNMPJCCARF-JVNHZCFISA-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	LOTUS Database	35616633
Broussonetia kazinoki SIEB.	Plant	KNApSAcK
Broussonetia papyrifera	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	-0.39	ALOGPS
logP	-0.83	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.25 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	92.83 m³·mol⁻¹	ChemAxon
Polarizability	37.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

8769889

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10594515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou L, Yu SY, Tang Y, Wang L: Facile Stereoselective Approach to Diverse Spiroheterocyclic Tetrahydropyrans: Concise Synthesis of (+)-Broussonetine G and H. Angew Chem Int Ed Engl. 2019 Oct 14;58(42):15016-15020. doi: 10.1002/anie.201907353. Epub 2019 Sep 9. [PubMed:31390139 ]
Zhao H, Kato A, Sato K, Jia YM, Yu CY: Total synthesis and glycosidase inhibition of broussonetine I and J(2). J Org Chem. 2013 Aug 16;78(16):7896-902. doi: 10.1021/jo4010553. Epub 2013 Jul 29. [PubMed:23829312 ]
Tsukamoto, D., et al. (2001). Tsukamoto, D., et al, Chem. Pharm. Bull. 49, 492 (2001). Chem. Pharm. Bull..

Showing NP-Card for Broussonetine R (NP0025682)

MOL for NP0025682 (Broussonetine R)

3D MOL for NP0025682 (Broussonetine R)

3D SDF for NP0025682 (Broussonetine R)

3D-SDF for NP0025682 (Broussonetine R)

PDB for NP0025682 (Broussonetine R)

3D PDB for NP0025682 (Broussonetine R)

SMILES for NP0025682 (Broussonetine R)

INCHI for NP0025682 (Broussonetine R)

Structure for NP0025682 (Broussonetine R)

3D Structure for NP0025682 (Broussonetine R)