NP-MRD: Showing NP-Card for 4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione (NP0036227)

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Record Information

Version

2.0

Created at

2021-06-20 19:27:23 UTC

Updated at

2021-06-30 00:07:46 UTC

NP-MRD ID

NP0036227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione

Provided By

JEOL Database JEOL Logo

Description

(2R,2'R,4R,4'R)-4,4'-dihydroxy-3,3',4,4'-tetrahydro-2,2'-binaphthalene-1,1'(2H,2'H)-dione, also known as (4Rs,4'RS)-dihydroxy-(2Rs,2'RS)-binaphthalene-1,1'-dione, belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane (2R,2'R,4R,4'R)-4,4'-dihydroxy-3,3',4,4'-tetrahydro-2,2'-binaphthalene-1,1'(2H,2'H)-dione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione is found in Rubia yunnanensis. 4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione was first documented in 2011 (Fan, J. -T., et al.). Based on a literature review very few articles have been published on (2R,2'R,4R,4'R)-4,4'-dihydroxy-3,3',4,4'-tetrahydro-2,2'-binaphthalene-1,1'(2H,2'H)-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121273D          

 42 45  0  0  0  0            999 V2000
   -2.3881   -0.7290    0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -0.7763    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5005    2.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1161   -0.2957    2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -0.0531    4.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.0163    5.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -0.2163    4.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -0.4478    3.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.6848    2.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5545    0.1398    3.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.3638    1.4853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0585   -1.1623    0.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2412    0.4215   -1.3970 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3353    0.4508   -2.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4655    1.8078   -3.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0700   -0.1021   -4.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 30  1  0  0  0  0
M  END

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
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   -1.7845   -0.5005    2.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1161   -0.2957    2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -0.0531    4.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.0163    5.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -0.2163    4.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -0.4478    3.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.6848    2.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5545    0.1398    3.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.3638    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -1.1623    0.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202121273D          

 42 45  0  0  0  0            999 V2000
   -2.3881   -0.7290    0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -0.7763    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5005    2.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1161   -0.2957    2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -0.0531    4.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.0163    5.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -0.2163    4.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -0.4478    3.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.6848    2.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5545    0.1398    3.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.3638    1.4853 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.1912   -1.0244   -0.9022 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.3353    0.4508   -2.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4655    1.8078   -3.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0700   -0.1021   -4.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -0.8567   -5.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
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 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 10 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C([H])C([H])=C([H])C([H])=C2C(=O)[C@]([H])(C1([H])[H])[C@]1([H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2[C@]([H])(O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c21-17-9-15(19(23)13-7-3-1-5-11(13)17)16-10-18(22)12-6-2-4-8-14(12)20(16)24/h1-8,15-18,21-22H,9-10H2/t15-,16-,17-,18-/m1/s1

> <INCHI_KEY>
KXYYQTOKRSUJFQ-BRSBDYLESA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.36

> <EXACT_MASS>
322.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.695467905009735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2'R,4R,4'R)-4,4'-dihydroxy-1H,1'H,2H,2'H,3H,3'H,4H,4'H-[2,2'-binaphthalene]-1,1'-dione

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.8337365266666668

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.16851639736701

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.745383089220862

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1329792852721043

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
89.8292

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'R,4R,4'R)-4,4'-dihydroxy-2H,2'H,3H,3'H,4H,4'H-[2,2'-binaphthalene]-1,1'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.3881   -0.7290    0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -0.7763    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5005    2.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1161   -0.2957    2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -0.0531    4.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.0163    5.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -0.2163    4.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -0.4478    3.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.6848    2.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5545    0.1398    3.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.3638    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -1.1623    0.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1912   -1.0244   -0.9022 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2412    0.4215   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    0.4508   -2.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4655    1.8078   -3.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -0.3574   -3.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700   -0.1021   -4.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -0.8567   -5.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737   -1.8846   -4.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246   -2.1630   -3.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0434   -1.4096   -2.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4682   -1.7458   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -2.6049   -0.6166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156   -0.3300    2.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    0.1043    4.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517    0.1710    6.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.1794    5.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -1.7320    3.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670   -0.1014    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -0.5869    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.7159    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -2.2273    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5514   -1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    0.9823   -1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    0.9530   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    0.0440   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463    2.2699   -3.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.7011   -5.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694   -0.6380   -6.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114   -2.4709   -4.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389   -2.9724   -2.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 13 12  1  0
 22 21  2  0
 23 24  2  0
 20 19  2  0
  3  4  2  0
  4  5  1  0
 19 18  1  0
  5  6  2  0
 18 17  2  0
  6  7  1  0
  7  8  2  0
  3  8  1  0
 22 23  1  0
 17 15  1  0
 15 14  1  0
 14 13  1  0
 13 23  1  0
  3  2  1  0
  8  9  1  0
  9 11  1  0
 11 12  1  0
 12  2  1  0
 22 17  1  0
  9 10  1  0
 15 16  1  0
  2  1  2  0
 21 42  1  0
 20 41  1  0
 19 40  1  0
 18 39  1  0
 15 37  1  6
 14 35  1  0
 14 36  1  0
 13 34  1  6
 16 38  1  0
 12 33  1  1
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  6
 11 31  1  0
 11 32  1  0
 10 30  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  O   UNK     0      -2.388  -0.729   0.143  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.489  -0.776   0.979  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.785  -0.500   2.413  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.116  -0.296   2.800  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.427  -0.053   4.137  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.412  -0.016   5.089  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.085  -0.216   4.706  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.748  -0.448   3.361  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.689  -0.685   2.962  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.555   0.140   3.736  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.916  -0.364   1.485  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.059  -1.162   0.619  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.191  -1.024  -0.902  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.241   0.422  -1.397  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.335   0.451  -2.922  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.466   1.808  -3.335  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.512  -0.357  -3.416  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.070  -0.102  -4.680  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.145  -0.857  -5.155  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.674  -1.885  -4.379  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.125  -2.163  -3.128  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.043  -1.410  -2.650  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.468  -1.746  -1.318  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.997  -2.605  -0.617  0.00  0.00           O+0
HETATM   25  H   UNK     0      -3.916  -0.330   2.062  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.461   0.104   4.435  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.652   0.171   6.133  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.303  -0.179   5.463  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.939  -1.732   3.171  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.467  -0.101   3.501  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.957  -0.587   1.223  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.789   0.716   1.327  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.025  -2.227   0.880  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.619  -1.551  -1.427  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.646   0.982  -1.079  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.104   0.953  -0.972  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.578   0.044  -3.372  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.346   2.270  -3.063  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.672   0.701  -5.298  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.569  -0.638  -6.132  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.511  -2.471  -4.748  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.539  -2.972  -2.530  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   12    1                                                  
CONECT    3    4    8    2                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   11   10   29                                             
CONECT   10    9   30                                                       
CONECT   11    9   12   31   32                                             
CONECT   12   13   11    2   33                                             
CONECT   13   12   14   23   34                                             
CONECT   14   15   13   35   36                                             
CONECT   15   17   14   16   37                                             
CONECT   16   15   38                                                       
CONECT   17   18   15   22                                                  
CONECT   18   19   17   39                                                  
CONECT   19   20   18   40                                                  
CONECT   20   21   19   41                                                  
CONECT   21   20   22   42                                                  
CONECT   22   21   23   17                                                  
CONECT   23   24   22   13                                                  
CONECT   24   23                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

RDKit          3D

42 45  0  0  0  0  0  0  0  0999 V2000
   -2.3881   -0.7290    0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -0.7763    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5005    2.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1161   -0.2957    2.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -0.0531    4.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.0163    5.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -0.2163    4.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -0.4478    3.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887   -0.6848    2.9618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5545    0.1398    3.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.3638    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -1.1623    0.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1912   -1.0244   -0.9022 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2412    0.4215   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    0.4508   -2.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4655    1.8078   -3.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -0.3574   -3.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700   -0.1021   -4.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -0.8567   -5.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737   -1.8846   -4.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1246   -2.1630   -3.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0434   -1.4096   -2.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4682   -1.7458   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -2.6049   -0.6166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156   -0.3300    2.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    0.1043    4.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517    0.1710    6.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.1794    5.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -1.7320    3.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4670   -0.1014    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -0.5869    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.7159    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -2.2273    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5514   -1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    0.9823   -1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    0.9530   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    0.0440   -3.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463    2.2699   -3.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.7011   -5.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694   -0.6380   -6.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114   -2.4709   -4.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389   -2.9724   -2.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 13 12  1  0
 22 21  2  0
 23 24  2  0
 20 19  2  0
  3  4  2  0
  4  5  1  0
 19 18  1  0
  5  6  2  0
 18 17  2  0
  6  7  1  0
  7  8  2  0
  3  8  1  0
 22 23  1  0
 17 15  1  0
 15 14  1  0
 14 13  1  0
 13 23  1  0
  3  2  1  0
  8  9  1  0
  9 11  1  0
 11 12  1  0
 12  2  1  0
 22 17  1  0
  9 10  1  0
 15 16  1  0
  2  1  2  0
 21 42  1  0
 20 41  1  0
 19 40  1  0
 18 39  1  0
 15 37  1  6
 14 35  1  0
 14 36  1  0
 13 34  1  6
 16 38  1  0
 12 33  1  1
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  6
 11 31  1  0
 11 32  1  0
 10 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4Rs,4'RS)-Dihydroxy-(2Rs,2'RS)-binaphthalene-1,1'-dione	ChEBI

Chemical Formula

C₂₀H₁₈O₄

Average Mass

322.3600 Da

Monoisotopic Mass

322.12051 Da

IUPAC Name

(2R,2'R,4R,4'R)-4,4'-dihydroxy-1H,1'H,2H,2'H,3H,3'H,4H,4'H-[2,2'-binaphthalene]-1,1'-dione

Traditional Name

(2R,2'R,4R,4'R)-4,4'-dihydroxy-2H,2'H,3H,3'H,4H,4'H-[2,2'-binaphthalene]-1,1'-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C2=C([H])C([H])=C([H])C([H])=C2C(=O)[C@]([H])(C1([H])[H])[C@]1([H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2[C@]([H])(O[H])C1([H])[H]

InChI Identifier

InChI=1S/C20H18O4/c21-17-9-15(19(23)13-7-3-1-5-11(13)17)16-10-18(22)12-6-2-4-8-14(12)20(16)24/h1-8,15-18,21-22H,9-10H2/t15-,16-,17-,18-/m1/s1

InChI Key

KXYYQTOKRSUJFQ-BRSBDYLESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rubia yunnanensis	JEOL database	Fan, J. -T., et al, J. Nat. Prod. 74, 2069 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Aryl alkyl ketone
Aryl ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:69515 )
secondary alcohol (CHEBI:69515 )
ring assembly (CHEBI:69515 )
tetralins (CHEBI:69515 )

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	1.8	ALOGPS
logP	1.83	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.83 m³·mol⁻¹	ChemAxon
Polarizability	34.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30786443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

69515

Good Scents ID

Not Available

References

General References

Fan, J. -T., et al. (2011). Fan, J. -T., et al, J. Nat. Prod. 74, 2069 (2011). J. Nat. Prod..

Showing NP-Card for 4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione (NP0036227)

MOL for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

3D MOL for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

3D SDF for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

3D-SDF for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

PDB for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

3D PDB for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

SMILES for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

INCHI for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

Structure for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)

3D Structure for NP0036227 (4R'S',4R'S'-dihydroxy-2R'S',2R'S'-binaphthalene-1,10-dione)