NP-MRD: Showing NP-Card for 12S-hydroxybromosphaerodiol (NP0025813)

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Record Information

Version

1.0

Created at

2021-06-19 17:50:09 UTC

Updated at

2021-06-29 23:50:59 UTC

NP-MRD ID

NP0025813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12S-hydroxybromosphaerodiol

Provided By

JEOL Database JEOL Logo

Description

12S-hydroxybromosphaerodiol is found in Sphaerococcus coronopifolius. It was first documented in 2001 (Etahiri, S., et al.). Based on a literature review very few articles have been published on 12S-hydroxybromosphaerodiol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119503D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192119503D          

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   -1.4366    0.2578    2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4471   -2.1084    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.2468   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242    2.2641    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -0.3865    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3628    0.4983    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.3800    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -1.0697   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.2133   -2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2705    3.3273   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131    3.0020   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    1.4680   -3.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    3.8109   -1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838    0.3095   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430    0.1465   -1.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    1.2917   -3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6981    3.1909   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124    3.6827   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    1.2200   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266    2.6206    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125    3.1028    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704    2.0079    3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0  0  0  0
 17 16  1  0  0  0  0
 16 14  1  0  0  0  0
 14 11  1  0  0  0  0
  5  4  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  4  2  1  0  0  0  0
 23 22  1  0  0  0  0
  9 38  1  6  0  0  0
 22 21  1  0  0  0  0
 11 13  1  6  0  0  0
 21 19  1  0  0  0  0
 17 18  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
  4 23  1  0  0  0  0
 11 12  1  0  0  0  0
  9  7  1  0  0  0  0
 14 15  1  0  0  0  0
  9 23  1  0  0  0  0
 10 39  1  1  0  0  0
 23 24  1  1  0  0  0
  6  5  2  0  0  0  0
 24 25  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
  2  3  1  0  0  0  0
  6 35  1  0  0  0  0
  5 34  1  0  0  0  0
  4 33  1  1  0  0  0
  7 36  1  1  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 17 48  1  1  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
 14 44  1  6  0  0  0
  8 37  1  0  0  0  0
  2 29  1  6  0  0  0
 13 43  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 15 45  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[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/C20H32Br2O3/c1-11(2)12-5-6-13(23)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(24)19(17,4)25/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15-,16-,17-,18+,19+,20-/m0/s1

> <INCHI_KEY>
WQVRLEHPQYWZGE-VHXYLUBJSA-N

> <FORMULA>
C20H32Br2O3

> <MOLECULAR_WEIGHT>
480.281

> <EXACT_MASS>
478.071821

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.06913649066868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.162939605999999

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.45948289702022

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.53449470911048

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9956225945748436

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
108.71129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.02e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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    0.2508   -0.8144    2.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -0.3213    1.7507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2022   -1.4769    1.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    0.5052    0.6378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9438    1.3985   -0.2562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3462    0.7941   -0.6800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3302    0.5626    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1358   -0.4594   -1.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    1.7471   -1.6498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6197    2.8852   -0.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    2.2745   -2.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492    2.9566   -2.2979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1734    3.8186   -3.8384 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    1.9926   -1.4998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4139    0.8769   -2.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779    2.8021   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9951    1.9876   -0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    1.3356    1.1875 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7389    2.4342    2.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    3.6725    2.8595 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -1.1716   -0.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172   -2.2557    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694   -2.1257   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    0.2783    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -0.2268    2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2791   -1.4099    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -1.8121    2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    1.0517    2.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -0.9046    3.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984   -1.4438    3.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366    0.2578    2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4471   -2.1084    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.2468   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242    2.2641    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -0.3865    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3628    0.4983    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.3800    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -1.0697   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.2133   -2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2705    3.3273   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131    3.0020   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    1.4680   -3.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    3.8109   -1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838    0.3095   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430    0.1465   -1.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    1.2917   -3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6981    3.1909   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124    3.6827   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    1.2200   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266    2.6206    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125    3.1028    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704    2.0079    3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 17 16  1  0
 16 14  1  0
 14 11  1  0
  5  4  1  0
  7  8  1  0
  9 10  1  0
  4  2  1  0
 23 22  1  0
  9 38  1  6
 22 21  1  0
 11 13  1  6
 21 19  1  0
 17 18  1  0
 10 19  1  0
 19 20  1  6
  4 23  1  0
 11 12  1  0
  9  7  1  0
 14 15  1  0
  9 23  1  0
 10 39  1  1
 23 24  1  1
  6  5  2  0
 24 25  1  0
  6  7  1  0
  2  1  1  0
 10 11  1  0
  2  3  1  0
  6 35  1  0
  5 34  1  0
  4 33  1  1
  7 36  1  1
 22 54  1  0
 22 55  1  0
 21 52  1  0
 21 53  1  0
 17 48  1  1
 16 46  1  0
 16 47  1  0
 14 44  1  6
  8 37  1  0
  2 29  1  6
 13 43  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 15 45  1  0
 24 56  1  0
 24 57  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 30  1  0
  3 31  1  0
  3 32  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       2.840  -1.554   0.316  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.371  -0.421   1.196  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.441  -1.002   2.142  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.287   0.387   1.992  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.547  -0.507   2.959  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.251  -0.814   2.846  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.640  -0.321   1.751  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.202  -1.477   1.121  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.042   0.505   0.638  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.944   1.399  -0.256  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.346   0.794  -0.680  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.330   0.563   0.495  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.136  -0.459  -1.330  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.123   1.747  -1.650  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.620   2.885  -0.926  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.308   2.275  -2.815  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.049   2.957  -2.298  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -0.173   3.819  -3.838  0.00  0.00          Br+0
HETATM   19  C   UNK     0      -0.124   1.993  -1.500  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.414   0.877  -2.441  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.078   2.802  -0.931  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.995   1.988  -0.023  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.281   1.336   1.188  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.739   2.434   2.168  0.00  0.00           C+0
HETATM   25 Br   UNK     0       2.088   3.672   2.860  0.00  0.00          Br+0
HETATM   26  H   UNK     0       2.263  -1.172  -0.526  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.217  -2.256   0.878  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.669  -2.126  -0.117  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.918   0.278   0.553  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.845  -0.227   2.801  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.279  -1.410   1.565  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.045  -1.812   2.762  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.883   1.052   2.628  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.109  -0.905   3.802  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.198  -1.444   3.611  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.437   0.258   2.226  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.447  -2.108   1.820  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.439  -0.247  -0.046  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.224   2.264   0.356  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.195  -0.387   1.011  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.363   0.498   0.127  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.295   1.380   1.222  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.773  -1.070  -0.651  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.991   1.213  -2.058  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.271   3.327  -1.501  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.913   3.002  -3.373  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.079   1.468  -3.520  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.322   3.811  -1.666  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.384   0.310  -2.925  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.043   0.147  -1.934  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.041   1.292  -3.237  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.698   3.191  -1.747  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.712   3.683  -0.389  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.459   1.220  -0.649  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.827   2.621   0.306  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.013   3.103   1.706  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.270   2.008   3.060  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    4    1    3   29                                             
CONECT    3    2   30   31   32                                             
CONECT    4    5    2   23   33                                             
CONECT    5    4    6   34                                                  
CONECT    6    5    7   35                                                  
CONECT    7    8    9    6   36                                             
CONECT    8    7   37                                                       
CONECT    9   10   38    7   23                                             
CONECT   10    9   19   39   11                                             
CONECT   11   14   13   12   10                                             
CONECT   12   11   40   41   42                                             
CONECT   13   11   43                                                       
CONECT   14   16   11   15   44                                             
CONECT   15   14   45                                                       
CONECT   16   17   14   46   47                                             
CONECT   17   19   16   18   48                                             
CONECT   18   17                                                            
CONECT   19   17   21   10   20                                             
CONECT   20   19   49   50   51                                             
CONECT   21   22   19   52   53                                             
CONECT   22   23   21   54   55                                             
CONECT   23   22    4    9   24                                             
CONECT   24   23   25   56   57                                             
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
    2.8403   -1.5536    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712   -0.4207    1.1965 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4413   -1.0017    2.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    0.3865    1.9923 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5469   -0.5067    2.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -0.8144    2.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -0.3213    1.7507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2022   -1.4769    1.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    0.5052    0.6378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9438    1.3985   -0.2562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3462    0.7941   -0.6800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3302    0.5626    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1358   -0.4594   -1.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    1.7471   -1.6498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6197    2.8852   -0.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    2.2745   -2.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492    2.9566   -2.2979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1734    3.8186   -3.8384 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    1.9926   -1.4998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4139    0.8769   -2.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779    2.8021   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9951    1.9876   -0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    1.3356    1.1875 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7389    2.4342    2.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    3.6725    2.8595 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -1.1716   -0.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172   -2.2557    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694   -2.1257   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    0.2783    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -0.2268    2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2791   -1.4099    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -1.8121    2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    1.0517    2.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -0.9046    3.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984   -1.4438    3.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366    0.2578    2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4471   -2.1084    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.2468   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2242    2.2641    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -0.3865    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3628    0.4983    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.3800    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -1.0697   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.2133   -2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2705    3.3273   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131    3.0020   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    1.4680   -3.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    3.8109   -1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838    0.3095   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430    0.1465   -1.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    1.2917   -3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6981    3.1909   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124    3.6827   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    1.2200   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266    2.6206    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125    3.1028    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704    2.0079    3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 17  1  0
 17 16  1  0
 16 14  1  0
 14 11  1  0
  5  4  1  0
  7  8  1  0
  9 10  1  0
  4  2  1  0
 23 22  1  0
  9 38  1  6
 22 21  1  0
 11 13  1  6
 21 19  1  0
 17 18  1  0
 10 19  1  0
 19 20  1  6
  4 23  1  0
 11 12  1  0
  9  7  1  0
 14 15  1  0
  9 23  1  0
 10 39  1  1
 23 24  1  1
  6  5  2  0
 24 25  1  0
  6  7  1  0
  2  1  1  0
 10 11  1  0
  2  3  1  0
  6 35  1  0
  5 34  1  0
  4 33  1  1
  7 36  1  1
 22 54  1  0
 22 55  1  0
 21 52  1  0
 21 53  1  0
 17 48  1  1
 16 46  1  0
 16 47  1  0
 14 44  1  6
  8 37  1  0
  2 29  1  6
 13 43  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 15 45  1  0
 24 56  1  0
 24 57  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂Br₂O₃

Average Mass

480.2810 Da

Monoisotopic Mass

478.07182 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]O[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/C20H32Br2O3/c1-11(2)12-5-6-13(23)16-17-18(3,7-8-20(12,16)10-21)14(22)9-15(24)19(17,4)25/h5-6,11-17,23-25H,7-10H2,1-4H3/t12-,13-,14-,15-,16-,17-,18+,19+,20-/m0/s1

InChI Key

WQVRLEHPQYWZGE-VHXYLUBJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃/CD₃OD (3:1), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃/CD₃OD (3:1), 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	Etahiri, S., et al, J. Nat. Prod. 64, 1024 (2001)

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
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
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	3.76	ALOGPS
logP	3.16	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.71 m³·mol⁻¹	ChemAxon
Polarizability	44.07 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

10213928

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21592263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Etahiri, S., et al. (2001). Etahiri, S., et al, J. Nat. Prod. 64, 1024 (2001). J. Nat. Prod..

Showing NP-Card for 12S-hydroxybromosphaerodiol (NP0025813)

MOL for NP0025813 (12S-hydroxybromosphaerodiol)

3D MOL for NP0025813 (12S-hydroxybromosphaerodiol)

3D SDF for NP0025813 (12S-hydroxybromosphaerodiol)

3D-SDF for NP0025813 (12S-hydroxybromosphaerodiol)

PDB for NP0025813 (12S-hydroxybromosphaerodiol)

3D PDB for NP0025813 (12S-hydroxybromosphaerodiol)

SMILES for NP0025813 (12S-hydroxybromosphaerodiol)

INCHI for NP0025813 (12S-hydroxybromosphaerodiol)

Structure for NP0025813 (12S-hydroxybromosphaerodiol)

3D Structure for NP0025813 (12S-hydroxybromosphaerodiol)