NP-MRD: Showing NP-Card for 1S-hydroperoxy-12R-hydroxy-bromosphaerol B (NP0037360)

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Record Information

Version

2.0

Created at

2021-06-20 20:18:06 UTC

Updated at

2021-06-30 00:09:31 UTC

NP-MRD ID

NP0037360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1S-hydroperoxy-12R-hydroxy-bromosphaerol B

Provided By

JEOL Database JEOL Logo

Description

CHEMBL603906 belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. 1S-hydroperoxy-12R-hydroxy-bromosphaerol B is found in Sphaerococcus coronopifolius. 1S-hydroperoxy-12R-hydroxy-bromosphaerol B was first documented in 2008 (Smyrniotopoulos, V., et al.). Based on a literature review very few articles have been published on CHEMBL603906.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122183D          

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M  END

     RDKit          3D

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  Mrv1652306202122183D          

 58 60  0  0  0  0            999 V2000
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   -4.4793   -0.3546    0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071   -1.2886    2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708   -0.0615    3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6630    0.4264    2.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4727   -2.2984    1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -1.5575    3.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -1.1142    3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184   -1.6000    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.9570    3.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893    0.2541   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827   -2.0509   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7956    0.9887   -3.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    1.5118   -2.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031    1.1012   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5797   -1.3967   -3.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1382   -0.4572   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9082   -3.4356    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7690   -3.4841   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -2.0758   -3.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.4338   -4.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    0.8919   -4.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -1.4743   -2.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554    1.2586   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614   -0.5524    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -2.0159   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460   -0.6588   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193    1.1929   -0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
  4  2  1  0  0  0  0
 14 12  1  0  0  0  0
 11 40  1  6  0  0  0
  5  4  1  0  0  0  0
 24 25  1  0  0  0  0
 11 10  1  0  0  0  0
 10 39  1  6  0  0  0
 11 12  1  0  0  0  0
 24 26  1  1  0  0  0
  4 16  1  0  0  0  0
 19 20  1  0  0  0  0
 10 16  1  0  0  0  0
 12 13  1  6  0  0  0
  7 10  1  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
 11 24  1  0  0  0  0
 16 17  1  1  0  0  0
 12 19  1  0  0  0  0
 21 22  1  0  0  0  0
 17 18  1  0  0  0  0
 22 24  1  0  0  0  0
 22 23  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  6  5  2  0  0  0  0
  8  9  1  0  0  0  0
  7 37  1  6  0  0  0
  6 36  1  0  0  0  0
  4 34  1  1  0  0  0
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 14 45  1  0  0  0  0
 22 53  1  6  0  0  0
  5 35  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 19 50  1  1  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 25 57  1  0  0  0  0
 26 58  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
  2 30  1  6  0  0  0
 23 54  1  0  0  0  0
  9 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OO[C@@]1([H])C([H])=C([H])[C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]2(C([H])([H])Br)C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])[C@@]([H])(Br)C([H])([H])[C@@]([H])(O[H])[C@](O[H])(C([H])([H])[H])[C@@]3([H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32Br2O4/c1-11(2)12-5-6-13(26-25)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(23)19(17,4)24/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15+,16-,17-,18+,19+,20-/m0/s1

> <INCHI_KEY>
SLASZMTUABGCGQ-CFAVNGNNSA-N

> <FORMULA>
C20H32Br2O4

> <MOLECULAR_WEIGHT>
496.28

> <EXACT_MASS>
494.066736

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.057857929538926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-5-hydroperoxy-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-3,4-diol

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
3.6122749833333327

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.58639352236328

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.705257530331219

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2519715751448404

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
110.06149999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-5-hydroperoxy-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthrene-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
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    1.7143    0.3707    2.6028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6322   -0.7757   -0.0002 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2483   -0.9811   -1.3312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6591   -0.6760   -2.6174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1329    0.8045   -2.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -1.6091   -2.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -1.4675   -1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -1.7173    0.0179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4323   -3.2088    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471   -4.5551   -0.0250 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1608   -1.0101   -3.8985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8454   -0.7932   -5.5752 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4235   -0.1805   -4.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.4535   -2.8340 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4466    0.4371   -2.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766   -0.3050   -1.4187 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7239   -0.9227   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696    1.0944   -1.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3071   -1.2886    2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1737   -1.1142    3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2474    0.9570    3.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893    0.2541   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827   -2.0509   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3049    1.5118   -2.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031    1.1012   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -2.6535   -2.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5797   -1.3967   -3.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1382   -0.4572   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9082   -3.4356    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7690   -3.4841   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -2.0758   -3.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.4338   -4.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    0.8919   -4.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -1.4743   -2.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554    1.2586   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614   -0.5524    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -2.0159   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460   -0.6588   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193    1.1929   -0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 16 15  1  0
 15 14  1  0
  4  2  1  0
 14 12  1  0
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  5  4  1  0
 24 25  1  0
 11 10  1  0
 10 39  1  6
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 24 26  1  1
  4 16  1  0
 19 20  1  0
 10 16  1  0
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  7 10  1  0
  2  1  1  0
  2  3  1  0
 11 24  1  0
 16 17  1  1
 12 19  1  0
 21 22  1  0
 17 18  1  0
 22 24  1  0
 22 23  1  0
  7  6  1  0
  7  8  1  0
  6  5  2  0
  8  9  1  0
  7 37  1  6
  6 36  1  0
  4 34  1  1
 15 46  1  0
 15 47  1  0
 14 44  1  0
 14 45  1  0
 22 53  1  6
  5 35  1  0
 21 51  1  0
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 19 50  1  1
 25 55  1  0
 25 56  1  0
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 26 58  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
 17 48  1  0
 17 49  1  0
  2 30  1  6
 23 54  1  0
  9 38  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.250   1.172   1.197  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.858  -0.231   1.238  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.851  -0.296   2.416  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.833  -1.417   1.294  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.005  -1.359   2.552  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.693  -1.103   2.563  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.144  -0.828   1.346  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.740   0.476   1.521  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.714   0.371   2.603  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.632  -0.776  -0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.248  -0.981  -1.331  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.659  -0.676  -2.617  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.133   0.805  -2.661  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.902  -1.609  -2.560  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.720  -1.468  -1.283  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.919  -1.717   0.018  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.432  -3.209   0.092  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -2.847  -4.555  -0.025  0.00  0.00          Br+0
HETATM   19  C   UNK     0       0.161  -1.010  -3.898  0.00  0.00           C+0
HETATM   20 Br   UNK     0      -0.845  -0.793  -5.575  0.00  0.00          Br+0
HETATM   21  C   UNK     0       1.424  -0.181  -4.016  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.328  -0.454  -2.834  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.447   0.437  -2.944  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.677  -0.305  -1.419  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.724  -0.923  -0.461  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.570   1.094  -1.139  0.00  0.00           O+0
HETATM   27  H   UNK     0      -2.738   1.360   0.254  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.034   1.934   1.276  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.547   1.342   2.018  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.479  -0.355   0.344  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.307  -1.289   2.491  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.371  -0.062   3.371  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.663   0.426   2.271  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.473  -2.298   1.420  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.510  -1.558   3.495  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.174  -1.114   3.519  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.918  -1.600   1.302  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.247   0.957   3.228  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.989   0.254  -0.063  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.483  -2.051  -1.387  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.796   0.989  -3.512  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.305   1.512  -2.739  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.703   1.101  -1.781  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.592  -2.654  -2.686  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.580  -1.397  -3.396  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.591  -2.130  -1.341  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.138  -0.457  -1.283  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.908  -3.436   1.024  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.769  -3.484  -0.729  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.423  -2.076  -3.901  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.969  -0.434  -4.936  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.217   0.892  -4.112  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.717  -1.474  -2.945  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.155   1.259  -2.496  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.661  -0.552   0.557  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.663  -2.016  -0.455  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.746  -0.659  -0.759  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.419   1.193  -0.177  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    4    1    3   30                                             
CONECT    3    2   31   32   33                                             
CONECT    4    2    5   16   34                                             
CONECT    5    4    6   35                                                  
CONECT    6    7    5   36                                                  
CONECT    7   10    6    8   37                                             
CONECT    8    7    9                                                       
CONECT    9    8   38                                                       
CONECT   10   11   39   16    7                                             
CONECT   11   40   10   12   24                                             
CONECT   12   14   11   13   19                                             
CONECT   13   12   41   42   43                                             
CONECT   14   15   12   44   45                                             
CONECT   15   16   14   46   47                                             
CONECT   16   15    4   10   17                                             
CONECT   17   16   18   48   49                                             
CONECT   18   17                                                            
CONECT   19   21   20   12   50                                             
CONECT   20   19                                                            
CONECT   21   19   22   51   52                                             
CONECT   22   21   24   23   53                                             
CONECT   23   22   54                                                       
CONECT   24   25   26   11   22                                             
CONECT   25   24   55   56   57                                             
CONECT   26   24   58                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   19                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
   -3.2502    1.1723    1.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584   -0.2310    1.2384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8514   -0.2958    2.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8327   -1.4167    1.2943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0047   -1.3590    2.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931   -1.1030    2.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -0.8281    1.3462 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7400    0.4755    1.5210 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7143    0.3707    2.6028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6322   -0.7757   -0.0002 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2483   -0.9811   -1.3312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6591   -0.6760   -2.6174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1329    0.8045   -2.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -1.6091   -2.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -1.4675   -1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -1.7173    0.0179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4323   -3.2088    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471   -4.5551   -0.0250 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1608   -1.0101   -3.8985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8454   -0.7932   -5.5752 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4235   -0.1805   -4.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.4535   -2.8340 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4466    0.4371   -2.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766   -0.3050   -1.4187 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7239   -0.9227   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696    1.0944   -1.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376    1.3602    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0343    1.9342    1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5470    1.3416    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793   -0.3546    0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071   -1.2886    2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708   -0.0615    3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6630    0.4264    2.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4727   -2.2984    1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -1.5575    3.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -1.1142    3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184   -1.6000    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.9570    3.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9893    0.2541   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827   -2.0509   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7956    0.9887   -3.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    1.5118   -2.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031    1.1012   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -2.6535   -2.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5797   -1.3967   -3.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909   -2.1296   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382   -0.4572   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9082   -3.4356    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7690   -3.4841   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -2.0758   -3.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.4338   -4.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    0.8919   -4.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -1.4743   -2.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554    1.2586   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614   -0.5524    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -2.0159   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460   -0.6588   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193    1.1929   -0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 16 15  1  0
 15 14  1  0
  4  2  1  0
 14 12  1  0
 11 40  1  6
  5  4  1  0
 24 25  1  0
 11 10  1  0
 10 39  1  6
 11 12  1  0
 24 26  1  1
  4 16  1  0
 19 20  1  0
 10 16  1  0
 12 13  1  6
  7 10  1  0
  2  1  1  0
  2  3  1  0
 11 24  1  0
 16 17  1  1
 12 19  1  0
 21 22  1  0
 17 18  1  0
 22 24  1  0
 22 23  1  0
  7  6  1  0
  7  8  1  0
  6  5  2  0
  8  9  1  0
  7 37  1  6
  6 36  1  0
  4 34  1  1
 15 46  1  0
 15 47  1  0
 14 44  1  0
 14 45  1  0
 22 53  1  6
  5 35  1  0
 21 51  1  0
 21 52  1  0
 19 50  1  1
 25 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
 17 48  1  0
 17 49  1  0
  2 30  1  6
 23 54  1  0
  9 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂Br₂O₄

Average Mass

496.2800 Da

Monoisotopic Mass

494.06674 Da

IUPAC Name

(1S,3R,4S,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-5-hydroperoxy-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-3,4-diol

Traditional Name

(1S,3R,4S,4aS,4bS,5S,8R,8aS,10aS)-1-bromo-8a-(bromomethyl)-5-hydroperoxy-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthrene-3,4-diol

CAS Registry Number

Not Available

SMILES

[H]OO[C@@]1([H])C([H])=C([H])[C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]2(C([H])([H])Br)C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])[C@@]([H])(Br)C([H])([H])[C@@]([H])(O[H])[C@](O[H])(C([H])([H])[H])[C@@]3([H])[C@]12[H]

InChI Identifier

InChI=1S/C20H32Br2O4/c1-11(2)12-5-6-13(26-25)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(23)19(17,4)24/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15+,16-,17-,18+,19+,20-/m0/s1

InChI Key

SLASZMTUABGCGQ-CFAVNGNNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sphaerococcus coronopifolius	JEOL database	Smyrniotopoulos, V., et al, Tetrahedron 64, 5184 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
Allylic hydroperoxide
Cyclic alcohol
Tertiary alcohol
1,2-diol
Secondary alcohol
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Organic oxygen compound
Organobromide
Organohalogen compound
Organooxygen compound
Hydrocarbon derivative
Alkyl halide
Alkyl bromide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.97	ALOGPS
logP	3.61	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.06 m³·mol⁻¹	ChemAxon
Polarizability	45.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

24653208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24850617

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Smyrniotopoulos, V., et al. (2008). Smyrniotopoulos, V., et al, Tetrahedron 64, 5184 (2008). Tetrahedron.

Showing NP-Card for 1S-hydroperoxy-12R-hydroxy-bromosphaerol B (NP0037360)

MOL for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

3D MOL for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

3D SDF for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

3D-SDF for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

PDB for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

3D PDB for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

SMILES for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

INCHI for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

Structure for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)

3D Structure for NP0037360 (1S-hydroperoxy-12R-hydroxy-bromosphaerol B)