NP-MRD: Showing NP-Card for bonannione B (NP0025221)

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Record Information

Version

2.0

Created at

2021-06-19 17:24:11 UTC

Updated at

2021-06-29 23:50:01 UTC

NP-MRD ID

NP0025221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bonannione B

Provided By

JEOL Database JEOL Logo

Description

bonannione B is found in Bonannia graeca. bonannione B was first documented in 2007 (Rosselli, S., et al.). Based on a literature review very few articles have been published on (5R,12S)-8-hydroxy-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-12-(4-hydroxyphenyl)-4,13-dioxatricyclo[7.4.0.0³,⁷]Trideca-1(9),2,7-trien-10-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119243D          

 59 62  0  0  0  0            999 V2000
    2.3579    6.8797    1.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577    5.4693    2.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2072    4.5334    1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029    5.1426    3.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944    3.8078    4.0694 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4955    3.3015    4.4445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4576    2.8832    3.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0423    4.0917    2.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5822    2.2464    3.9467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    1.8764    2.3052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7200    0.5935    2.9587 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4129   -0.3743    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22 23  1  0  0  0  0
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  6  7  1  0  0  0  0
  4  2  2  3  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119243D          

 59 62  0  0  0  0            999 V2000
    2.3579    6.8797    1.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577    5.4693    2.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2233   -4.6894   -4.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209   -2.4803   -1.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    1.4777    1.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    7.5380    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426    6.8884    0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    7.3062    1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161    4.9173    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    3.5247    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6894    4.4495    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    5.9300    3.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    3.0408    3.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    3.9275    5.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    2.4406    5.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075    4.0505    5.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7888    0.6749    3.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7493   -0.0497   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6477   -3.1018   -2.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0547   -5.2931   -4.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -6.2710   -6.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551   -5.6898   -5.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8527   -4.5329   -4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
 13 14  2  0  0  0  0
 23 24  2  0  0  0  0
 12 17  2  0  0  0  0
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 17 16  1  0  0  0  0
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 15 14  1  0  0  0  0
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 15 16  2  0  0  0  0
 28 29  2  0  0  0  0
 29 23  1  0  0  0  0
  2  1  1  0  0  0  0
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  5  4  1  0  0  0  0
 19 20  2  0  0  0  0
  2  3  1  0  0  0  0
 17 18  1  0  0  0  0
 12 13  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  4  2  2  3  0  0  0
 15 30  1  0  0  0  0
 16 19  1  0  0  0  0
 13 31  1  0  0  0  0
 31 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10  7  1  0  0  0  0
 19 21  1  0  0  0  0
  7  8  1  0  0  0  0
 21 22  1  0  0  0  0
  7  9  1  1  0  0  0
 22 30  1  0  0  0  0
 10 47  1  6  0  0  0
  6 41  1  0  0  0  0
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  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  4 38  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  0  0  0  0
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 14 50  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
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 28 58  1  0  0  0  0
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 11 48  1  0  0  0  0
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  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
  9 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC2=C(C(O[H])=C3C(O[C@]([H])(C3([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])=C2[H])C(=O)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O6/c1-14(2)5-4-10-25(3,29)22-11-17-20(31-22)13-21-23(24(17)28)18(27)12-19(30-21)15-6-8-16(26)9-7-15/h5-9,13,19,22,26,28-29H,4,10-12H2,1-3H3/t19-,22+,25-/m0/s1

> <INCHI_KEY>
WTGUNSGYPQJOLT-SWHJIRTISA-N

> <FORMULA>
C25H28O6

> <MOLECULAR_WEIGHT>
424.493

> <EXACT_MASS>
424.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
47.3728241537441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,12S)-8-hydroxy-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-12-(4-hydroxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
4.825375368666666

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.565023548944147

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.75823574310664

> <JCHEM_PKA_STRONGEST_BASIC>
-3.22873568513851

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
117.82679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,12S)-8-hydroxy-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-12-(4-hydroxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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   -2.3631   -4.4734   -2.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -5.1296   -4.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -5.5599   -5.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -6.2046   -6.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420   -5.3459   -5.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8403    1.4777    1.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    7.5380    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426    6.8884    0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    7.3062    1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161    4.9173    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    3.5247    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6894    4.4495    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    5.9300    3.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    3.0408    3.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    3.9275    5.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    2.4406    5.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075    4.0505    5.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    4.5602    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076    4.8462    3.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100    3.8024    1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    1.8614    3.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    2.3693    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1773    0.3155    3.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7888    0.6749    3.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7493   -0.0497   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009   -3.1262    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -4.9818   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446   -5.3565   -1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477   -3.1018   -2.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9717   -4.1395   -2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547   -5.2931   -4.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -6.2710   -6.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551   -5.6898   -5.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8527   -4.5329   -4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 13 14  2  0
 23 24  2  0
 12 17  2  0
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 17 16  1  0
 25 26  2  0
 15 14  1  0
 26 28  1  0
 15 16  2  0
 28 29  2  0
 29 23  1  0
  2  1  1  0
 26 27  1  0
  5  4  1  0
 19 20  2  0
  2  3  1  0
 17 18  1  0
 12 13  1  0
  6  5  1  0
  6  7  1  0
  4  2  2  3
 15 30  1  0
 16 19  1  0
 13 31  1  0
 31 10  1  0
 10 11  1  0
 11 12  1  0
 10  7  1  0
 19 21  1  0
  7  8  1  0
 21 22  1  0
  7  9  1  1
 22 30  1  0
 10 47  1  6
  6 41  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  4 38  1  0
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  1 33  1  0
  1 34  1  0
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 14 50  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  6
 24 55  1  0
 25 56  1  0
 28 58  1  0
 29 59  1  0
 27 57  1  0
 18 51  1  0
 11 48  1  0
 11 49  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  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  C   UNK     0       2.358   6.880   1.675  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.458   5.469   2.199  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.207   4.533   1.291  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.903   5.143   3.383  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.894   3.808   4.069  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.496   3.301   4.444  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.458   2.883   3.301  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.042   4.092   2.556  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.582   2.246   3.947  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.172   1.876   2.305  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.720   0.594   2.959  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.413  -0.374   1.880  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.503   0.189   1.007  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.029  -0.510  -0.061  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.589  -1.819  -0.262  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.328  -2.407   0.627  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.836  -1.677   1.710  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.718  -2.191   2.616  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.698  -3.819   0.416  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.505  -4.361   1.168  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.002  -4.548  -0.694  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.286  -3.552  -1.809  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.978  -4.239  -2.973  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.363  -4.473  -2.966  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.982  -5.130  -4.033  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.214  -5.560  -5.109  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.776  -6.205  -6.171  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.842  -5.346  -5.134  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.223  -4.689  -4.068  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.121  -2.480  -1.339  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.840   1.478   1.324  0.00  0.00           O+0
HETATM   32  H   UNK     0       1.804   7.538   2.352  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.843   6.888   0.708  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.357   7.306   1.541  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.216   4.917   1.106  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.316   3.525   1.693  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.689   4.449   0.330  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.401   5.930   3.947  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.426   3.041   3.503  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.464   3.928   5.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.628   2.441   5.115  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.008   4.051   5.072  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.316   4.560   1.888  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.408   4.846   3.262  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.910   3.802   1.951  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.128   1.861   3.234  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.970   2.369   1.732  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.177   0.316   3.868  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.789   0.675   3.174  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.749  -0.050  -0.729  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.901  -3.126   2.371  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.921  -4.982  -0.282  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.645  -5.356  -1.052  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.648  -3.102  -2.179  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.972  -4.139  -2.128  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.055  -5.293  -4.005  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.733  -6.271  -6.022  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.255  -5.690  -5.981  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.853  -4.533  -4.104  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   35   36   37                                             
CONECT    4    5    2   38                                                  
CONECT    5    4    6   39   40                                             
CONECT    6    5    7   41   42                                             
CONECT    7    6   10    8    9                                             
CONECT    8    7   43   44   45                                             
CONECT    9    7   46                                                       
CONECT   10   31   11    7   47                                             
CONECT   11   10   12   48   49                                             
CONECT   12   17   13   11                                                  
CONECT   13   14   12   31                                                  
CONECT   14   13   15   50                                                  
CONECT   15   14   16   30                                                  
CONECT   16   17   15   19                                                  
CONECT   17   12   16   18                                                  
CONECT   18   17   51                                                       
CONECT   19   20   16   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   52   53                                             
CONECT   22   23   21   30   54                                             
CONECT   23   22   24   29                                                  
CONECT   24   23   25   55                                                  
CONECT   25   24   26   56                                                  
CONECT   26   25   28   27                                                  
CONECT   27   26   57                                                       
CONECT   28   26   29   58                                                  
CONECT   29   28   23   59                                                  
CONECT   30   15   22                                                       
CONECT   31   13   10                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   14                                                            
CONECT   51   18                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

RDKit          3D

59 62  0  0  0  0  0  0  0  0999 V2000
    2.3579    6.8797    1.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577    5.4693    2.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2072    4.5334    1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029    5.1426    3.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944    3.8078    4.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4955    3.3015    4.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4576    2.8832    3.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0423    4.0917    2.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5822    2.2464    3.9467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    1.8764    2.3052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7200    0.5935    2.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129   -0.3743    1.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033    0.1887    1.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -0.5101   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -1.8190   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -2.4069    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364   -1.6771    1.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179   -2.1906    2.6165 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979   -3.8191    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -4.3605    1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023   -4.5478   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859   -3.5517   -1.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9775   -4.2395   -2.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631   -4.4734   -2.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -5.1296   -4.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -5.5599   -5.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -6.2046   -6.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420   -5.3459   -5.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233   -4.6894   -4.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209   -2.4803   -1.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    1.4777    1.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    7.5380    2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426    6.8884    0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574    7.3062    1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161    4.9173    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    3.5247    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6894    4.4495    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    5.9300    3.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    3.0408    3.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    3.9275    5.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    2.4406    5.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075    4.0505    5.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    4.5602    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076    4.8462    3.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100    3.8024    1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    1.8614    3.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    2.3693    1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1773    0.3155    3.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7888    0.6749    3.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7493   -0.0497   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9009   -3.1262    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208   -4.9818   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446   -5.3565   -1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477   -3.1018   -2.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9717   -4.1395   -2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547   -5.2931   -4.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -6.2710   -6.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551   -5.6898   -5.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8527   -4.5329   -4.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 13 14  2  0
 23 24  2  0
 12 17  2  0
 24 25  1  0
 17 16  1  0
 25 26  2  0
 15 14  1  0
 26 28  1  0
 15 16  2  0
 28 29  2  0
 29 23  1  0
  2  1  1  0
 26 27  1  0
  5  4  1  0
 19 20  2  0
  2  3  1  0
 17 18  1  0
 12 13  1  0
  6  5  1  0
  6  7  1  0
  4  2  2  3
 15 30  1  0
 16 19  1  0
 13 31  1  0
 31 10  1  0
 10 11  1  0
 11 12  1  0
 10  7  1  0
 19 21  1  0
  7  8  1  0
 21 22  1  0
  7  9  1  1
 22 30  1  0
 10 47  1  6
  6 41  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  4 38  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
 14 50  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  6
 24 55  1  0
 25 56  1  0
 28 58  1  0
 29 59  1  0
 27 57  1  0
 18 51  1  0
 11 48  1  0
 11 49  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₆

Average Mass

424.4930 Da

Monoisotopic Mass

424.18859 Da

IUPAC Name

(5R,12S)-8-hydroxy-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-12-(4-hydroxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

Traditional Name

(5R,12S)-8-hydroxy-5-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-12-(4-hydroxyphenyl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(9),2,7-trien-10-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC2=C(C(O[H])=C3C(O[C@]([H])(C3([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])=C2[H])C(=O)C1([H])[H]

InChI Identifier

InChI=1S/C25H28O6/c1-14(2)5-4-10-25(3,29)22-11-17-20(31-22)13-21-23(24(17)28)18(27)12-19(30-21)15-6-8-16(26)9-7-15/h5-9,13,19,22,26,28-29H,4,10-12H2,1-3H3/t19-,22+,25-/m0/s1

InChI Key

WTGUNSGYPQJOLT-SWHJIRTISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Bonannia graeca	JEOL database	Rosselli, S., et al, Eur. J. Org. Chem. 2007, 2504.

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	3.73	ALOGPS
logP	4.83	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.83 m³·mol⁻¹	ChemAxon
Polarizability	47.37 Å³	ChemAxon
Number of Rings	4	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102082602

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rosselli, S., et al. (2007). Rosselli, S., et al, Eur. J. Org. Chem. 2007, 2504.. Eur. J. Org. Chem..

Showing NP-Card for bonannione B (NP0025221)

MOL for NP0025221 (bonannione B)

3D MOL for NP0025221 (bonannione B)

3D SDF for NP0025221 (bonannione B)

3D-SDF for NP0025221 (bonannione B)

PDB for NP0025221 (bonannione B)

3D PDB for NP0025221 (bonannione B)

SMILES for NP0025221 (bonannione B)

INCHI for NP0025221 (bonannione B)

Structure for NP0025221 (bonannione B)

3D Structure for NP0025221 (bonannione B)