NP-MRD: Showing NP-Card for Caraphenol B (NP0025384)

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Record Information

Version

2.0

Created at

2021-06-19 17:31:09 UTC

Updated at

2021-06-29 23:50:18 UTC

NP-MRD ID

NP0025384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caraphenol B

Provided By

JEOL Database JEOL Logo

Description

Caraphenol B is found in Caragana sinica. Caraphenol B was first documented in 2011 (PMID: 21942557). Based on a literature review very few articles have been published on (1R,2R,3R)-3-(3,5-dihydroxyphenyl)-1-(4-hydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol (PMID: 22209460).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119313D          

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M  END

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M  END


  Mrv1652306192119313D          

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    1.2322    3.0725    2.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586   -0.5637   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8306   -0.2678   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565    0.3450    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027    1.0101    3.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.7325    2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -0.5963    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520   -3.1188    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989   -5.0860   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923   -3.3009   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163    0.1709   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    1.2583    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499    3.4135   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133    5.3141   -3.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    3.7216   -4.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    0.5676   -4.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865    0.1577   -2.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628    0.8919    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.4307   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    4.5513   -0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590    6.2565    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    4.8254    3.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    2.6839    3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 35  2  0  0  0  0
 35 29  1  0  0  0  0
 19 28  1  0  0  0  0
 20 27  2  0  0  0  0
 28 10  1  0  0  0  0
 27 25  1  0  0  0  0
 10 11  1  0  0  0  0
 25 24  2  0  0  0  0
 12 13  2  0  0  0  0
 24 22  1  0  0  0  0
 10  2  1  0  0  0  0
 22 21  2  0  0  0  0
 21 20  1  0  0  0  0
 11 18  2  0  0  0  0
 32 33  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
 28 29  1  0  0  0  0
  2  3  1  0  0  0  0
 15 16  2  0  0  0  0
  2  1  2  0  0  0  0
 29 30  2  0  0  0  0
  3  4  2  0  0  0  0
 16 18  1  0  0  0  0
  4  5  1  0  0  0  0
 30 31  1  0  0  0  0
  5  6  2  0  0  0  0
 13 15  1  0  0  0  0
  6  8  1  0  0  0  0
 31 32  2  0  0  0  0
  8  9  2  0  0  0  0
  9  3  1  0  0  0  0
 11 12  1  0  0  0  0
  6  7  1  0  0  0  0
 32 34  1  0  0  0  0
 13 14  1  0  0  0  0
 18 19  1  0  0  0  0
 16 17  1  0  0  0  0
 15 44  1  0  0  0  0
 12 42  1  0  0  0  0
 19 46  1  1  0  0  0
 28 52  1  1  0  0  0
 10 41  1  1  0  0  0
 30 53  1  0  0  0  0
 31 54  1  0  0  0  0
 34 56  1  0  0  0  0
 35 57  1  0  0  0  0
 27 51  1  0  0  0  0
 24 49  1  0  0  0  0
 21 47  1  0  0  0  0
 33 55  1  0  0  0  0
 23 48  1  0  0  0  0
 26 50  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
  7 38  1  0  0  0  0
 14 43  1  0  0  0  0
 17 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025384

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O7/c29-17-5-1-14(2-6-17)24-25(16-9-19(31)11-20(32)10-16)26-22(12-21(33)13-23(26)34)27(24)28(35)15-3-7-18(30)8-4-15/h1-13,24-25,27,29-34H/t24-,25+,27+/m1/s1

> <INCHI_KEY>
FQVHLQDBUOYEEX-OBDYRVMHSA-N

> <FORMULA>
C28H22O7

> <MOLECULAR_WEIGHT>
470.477

> <EXACT_MASS>
470.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.24106641113279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R)-3-(3,5-dihydroxyphenyl)-1-(4-hydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
4.9781691273333335

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.886836357114973

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.718308296330474

> <JCHEM_PKA_STRONGEST_BASIC>
-5.456362536714676

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
130.16879999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R)-3-(3,5-dihydroxyphenyl)-1-(4-hydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
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    1.9395   -2.6129    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -3.3497   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1616   -2.7239   -0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0837    0.9189    0.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0241    1.6754   -1.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879    2.9618   -1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5533    3.6882   -2.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242    4.9269   -2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    3.1660   -3.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905    1.8997   -3.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.4104   -4.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    1.1507   -2.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    1.0376    1.0173 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1599    2.3671    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4064    2.9279    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    4.1472    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719    4.8174    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044    6.0074    1.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5586   -0.5637   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8306   -0.2678   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565    0.3450    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027    1.0101    3.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.7325    2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -0.5963    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520   -3.1188    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989   -5.0860   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923   -3.3009   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163    0.1709   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    1.2583    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499    3.4135   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133    5.3141   -3.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    3.7216   -4.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    0.5676   -4.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865    0.1577   -2.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628    0.8919    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.4307   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    4.5513   -0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590    6.2565    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    4.8254    3.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    2.6839    3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 35  2  0
 35 29  1  0
 19 28  1  0
 20 27  2  0
 28 10  1  0
 27 25  1  0
 10 11  1  0
 25 24  2  0
 12 13  2  0
 24 22  1  0
 10  2  1  0
 22 21  2  0
 21 20  1  0
 11 18  2  0
 32 33  1  0
 19 20  1  0
 22 23  1  0
 25 26  1  0
 28 29  1  0
  2  3  1  0
 15 16  2  0
  2  1  2  0
 29 30  2  0
  3  4  2  0
 16 18  1  0
  4  5  1  0
 30 31  1  0
  5  6  2  0
 13 15  1  0
  6  8  1  0
 31 32  2  0
  8  9  2  0
  9  3  1  0
 11 12  1  0
  6  7  1  0
 32 34  1  0
 13 14  1  0
 18 19  1  0
 16 17  1  0
 15 44  1  0
 12 42  1  0
 19 46  1  1
 28 52  1  1
 10 41  1  1
 30 53  1  0
 31 54  1  0
 34 56  1  0
 35 57  1  0
 27 51  1  0
 24 49  1  0
 21 47  1  0
 33 55  1  0
 23 48  1  0
 26 50  1  0
  4 36  1  0
  5 37  1  0
  8 39  1  0
  9 40  1  0
  7 38  1  0
 14 43  1  0
 17 45  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.131  -0.263  -1.259  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.209  -0.158  -0.034  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.565   0.041   0.569  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.687  -0.222  -0.234  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.980  -0.055   0.269  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.150   0.383   1.576  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.390   0.563   2.111  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.052   0.657   2.383  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.758   0.486   1.882  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.011  -0.249   0.880  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.045  -1.228   0.369  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.940  -2.613   0.352  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.009  -3.350  -0.148  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.892  -4.710  -0.149  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.162  -2.724  -0.632  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.248  -1.333  -0.621  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.383  -0.771  -1.122  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.197  -0.584  -0.114  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.084   0.919   0.022  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.024   1.675  -1.290  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.588   2.962  -1.360  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.553   3.688  -2.548  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.124   4.927  -2.549  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.955   3.166  -3.687  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.390   1.900  -3.623  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.790   1.410  -4.746  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.428   1.151  -2.447  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.876   1.038   1.017  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.160   2.367   1.147  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.406   2.928   0.105  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.258   4.147   0.268  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.172   4.817   1.480  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.804   6.007   1.683  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.568   4.290   2.528  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.232   3.072   2.362  0.00  0.00           C+0
HETATM   36  H   UNK     0      -2.559  -0.564  -1.260  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.831  -0.268  -0.372  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.056   0.345   1.438  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.203   1.010   3.400  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.928   0.733   2.537  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.702  -0.596   1.873  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.052  -3.119   0.718  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.699  -5.086  -0.538  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.992  -3.301  -1.025  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.216   0.171  -1.298  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.983   1.258   0.557  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.050   3.414  -0.484  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.013   5.314  -3.434  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.915   3.722  -4.617  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.361   0.568  -4.515  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.986   0.158  -2.433  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.363   0.892   2.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.323   2.431  -0.860  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.829   4.551  -0.562  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.259   6.256   0.862  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.632   4.825   3.471  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.808   2.684   3.200  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   10    3    1                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6   37                                                  
CONECT    6    5    8    7                                                  
CONECT    7    6   38                                                       
CONECT    8    6    9   39                                                  
CONECT    9    8    3   40                                                  
CONECT   10   28   11    2   41                                             
CONECT   11   10   18   12                                                  
CONECT   12   13   11   42                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13   43                                                       
CONECT   15   16   13   44                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   45                                                       
CONECT   18   11   16   19                                                  
CONECT   19   28   20   18   46                                             
CONECT   20   27   21   19                                                  
CONECT   21   22   20   47                                                  
CONECT   22   24   21   23                                                  
CONECT   23   22   48                                                       
CONECT   24   25   22   49                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25   50                                                       
CONECT   27   20   25   51                                                  
CONECT   28   19   10   29   52                                             
CONECT   29   35   28   30                                                  
CONECT   30   29   31   53                                                  
CONECT   31   30   32   54                                                  
CONECT   32   33   31   34                                                  
CONECT   33   32   55                                                       
CONECT   34   35   32   56                                                  
CONECT   35   34   29   57                                                  
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   17                                                            
CONECT   46   19                                                            
CONECT   47   21                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
CONECT   53   30                                                            
CONECT   54   31                                                            
CONECT   55   33                                                            
CONECT   56   34                                                            
CONECT   57   35                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

RDKit          3D

57 61  0  0  0  0  0  0  0  0999 V2000
   -0.1305   -0.2629   -1.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -0.1584   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    0.0408    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6873   -0.2224   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9804   -0.0547    0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1503    0.3832    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3904    0.5629    2.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523    0.6565    2.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7580    0.4863    1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0109   -0.2493    0.8802 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0454   -1.2279    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9395   -2.6129    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -3.3497   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8915   -4.7098   -0.1493 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1616   -2.7239   -0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482   -1.3333   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3826   -0.7713   -1.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966   -0.5839   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    0.9189    0.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0241    1.6754   -1.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879    2.9618   -1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5533    3.6882   -2.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242    4.9269   -2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    3.1660   -3.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905    1.8997   -3.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.4104   -4.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    1.1507   -2.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    1.0376    1.0173 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1599    2.3671    1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4064    2.9279    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    4.1472    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719    4.8174    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044    6.0074    1.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683    4.2898    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2322    3.0725    2.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586   -0.5637   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8306   -0.2678   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0565    0.3450    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027    1.0101    3.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.7325    2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -0.5963    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520   -3.1188    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989   -5.0860   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923   -3.3009   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163    0.1709   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    1.2583    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499    3.4135   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133    5.3141   -3.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    3.7216   -4.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    0.5676   -4.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865    0.1577   -2.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628    0.8919    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    2.4307   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    4.5513   -0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590    6.2565    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    4.8254    3.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    2.6839    3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 35  2  0
 35 29  1  0
 19 28  1  0
 20 27  2  0
 28 10  1  0
 27 25  1  0
 10 11  1  0
 25 24  2  0
 12 13  2  0
 24 22  1  0
 10  2  1  0
 22 21  2  0
 21 20  1  0
 11 18  2  0
 32 33  1  0
 19 20  1  0
 22 23  1  0
 25 26  1  0
 28 29  1  0
  2  3  1  0
 15 16  2  0
  2  1  2  0
 29 30  2  0
  3  4  2  0
 16 18  1  0
  4  5  1  0
 30 31  1  0
  5  6  2  0
 13 15  1  0
  6  8  1  0
 31 32  2  0
  8  9  2  0
  9  3  1  0
 11 12  1  0
  6  7  1  0
 32 34  1  0
 13 14  1  0
 18 19  1  0
 16 17  1  0
 15 44  1  0
 12 42  1  0
 19 46  1  1
 28 52  1  1
 10 41  1  1
 30 53  1  0
 31 54  1  0
 34 56  1  0
 35 57  1  0
 27 51  1  0
 24 49  1  0
 21 47  1  0
 33 55  1  0
 23 48  1  0
 26 50  1  0
  4 36  1  0
  5 37  1  0
  8 39  1  0
  9 40  1  0
  7 38  1  0
 14 43  1  0
 17 45  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₇

Average Mass

470.4770 Da

Monoisotopic Mass

470.13655 Da

IUPAC Name

(1R,2R,3R)-3-(3,5-dihydroxyphenyl)-1-(4-hydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

Traditional Name

(1R,2R,3R)-3-(3,5-dihydroxyphenyl)-1-(4-hydroxybenzoyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H22O7/c29-17-5-1-14(2-6-17)24-25(16-9-19(31)11-20(32)10-16)26-22(12-21(33)13-23(26)34)27(24)28(35)15-3-7-18(30)8-4-15/h1-13,24-25,27,29-34H/t24-,25+,27+/m1/s1

InChI Key

FQVHLQDBUOYEEX-OBDYRVMHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Caragana sinica	JEOL database	Luo, H.-F., et al, Tetrahedron 57, 4849 (2001)

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	4.07	ALOGPS
logP	4.98	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.17 m³·mol⁻¹	ChemAxon
Polarizability	48.24 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

425062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

484753

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jin Q, Han XH, Hong SS, Lee C, Choe S, Lee D, Kim Y, Hong JT, Lee MK, Hwang BY: Antioxidative oligostilbenes from Caragana sinica. Bioorg Med Chem Lett. 2012 Jan 15;22(2):973-6. doi: 10.1016/j.bmcl.2011.12.012. Epub 2011 Dec 9. [PubMed:22209460 ]
Snyder SA, Brill ZG: Structural revision and total synthesis of caraphenol B and C. Org Lett. 2011 Oct 21;13(20):5524-7. doi: 10.1021/ol2022406. Epub 2011 Sep 26. [PubMed:21942557 ]
Luo, H.-F., et al. (2001). Luo, H.-F., et al, Tetrahedron 57, 4849 (2001). Tetrahedron.

Showing NP-Card for Caraphenol B (NP0025384)

MOL for NP0025384 (Caraphenol B)

3D MOL for NP0025384 (Caraphenol B)

3D SDF for NP0025384 (Caraphenol B)

3D-SDF for NP0025384 (Caraphenol B)

PDB for NP0025384 (Caraphenol B)

3D PDB for NP0025384 (Caraphenol B)

SMILES for NP0025384 (Caraphenol B)

INCHI for NP0025384 (Caraphenol B)

Structure for NP0025384 (Caraphenol B)

3D Structure for NP0025384 (Caraphenol B)