NP-MRD: Showing NP-Card for Epi-deacetylgriseusin B (NP0007274)

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Record Information

Version

1.0

Created at

2020-12-09 04:06:54 UTC

Updated at

2021-07-15 16:57:08 UTC

NP-MRD ID

NP0007274

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epi-deacetylgriseusin B

Provided By

NPAtlas

Description

Epi-deacetylgriseusin B belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Epi-deacetylgriseusin B is found in Nocardiopsis sp. It was first documented in 2007 (PMID: 17877337). Based on a literature review very few articles have been published on epi-deacetylgriseusin B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118393D          

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     RDKit          3D

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  Mrv1652306242118393D          

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 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  8 29  1  0  0  0  0
 29  2  1  0  0  0  0
 17  8  1  0  0  0  0
 26 20  1  0  0  0  0
 27 16  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  2 33  1  6  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  6  0  0  0
  5 37  1  0  0  0  0
  6 38  1  6  0  0  0
  7 39  1  0  0  0  0
 10 40  1  1  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 14 43  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 24 48  1  0  0  0  0
 25 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])O[C@]2(O[C@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(O[H])[C@@]2([H])O[H])C2=C(C(=O)C3=C([H])C([H])=C([H])C(O[H])=C3C2=O)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O9/c1-8-5-13(22)19(27)20(28-8)16-11(6-9(29-20)7-14(23)24)17(25)10-3-2-4-12(21)15(10)18(16)26/h2-4,8-9,13,19,21-22,27H,5-7H2,1H3,(H,23,24)/t8-,9+,13+,19-,20-/m1/s1

> <INCHI_KEY>
VNNLNRPAIDMNEB-WPPLHGJESA-N

> <FORMULA>
C20H20O9

> <MOLECULAR_WEIGHT>
404.371

> <EXACT_MASS>
404.110732224

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.93817976807137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,3S,3'R,4'S,6'R)-3',4',9-trihydroxy-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetic acid

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
0.8529886546666661

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.189255934175929

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5461941497863547

> <JCHEM_PKA_STRONGEST_BASIC>
-3.262438859150456

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
97.2557

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,3'R,4'S,6'R)-3',4',9-trihydroxy-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-ylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.5381   -2.4857    2.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -1.7721    0.8489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8687   -2.7758   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4090   -2.0676   -1.4650 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3031   -2.7214   -2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840   -0.6132   -1.3609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2964    0.0937   -1.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8104   -0.0890    0.0140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6749    0.9288    0.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829    2.1946    0.2433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3558    3.1042   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5971    3.0854    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6259    2.5716   -0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275    3.6281    1.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    2.4961   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    1.4711   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.2578    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -0.8340    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1787   -1.9808    0.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272   -0.5730    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753   -1.5451    0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -2.8315    0.8460 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -1.1664    0.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7131    0.1083    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7456    1.0548   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192    0.7198    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175    1.7807   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8317    2.9373   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670   -1.0376    1.0205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.7526    2.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -3.1222    2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137   -3.1132    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -1.1188    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887   -3.5253    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7969   -3.4054   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285   -2.2300   -2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -2.3005   -2.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3358   -0.3371   -2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763   -0.5549   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058    2.5664    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    2.9031   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482    4.1567   -0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7740    4.6174    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    2.5094   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060    3.4747   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -3.2481    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0430   -1.9502    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7740    0.4024    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359    2.0892   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  8 29  1  0
 29  2  1  0
 17  8  1  0
 26 20  1  0
 27 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  6 38  1  6
  7 39  1  0
 10 40  1  1
 11 41  1  0
 11 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.538  -2.486   2.122  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.128  -1.772   0.849  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.869  -2.776  -0.241  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.409  -2.068  -1.465  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.303  -2.721  -2.063  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.184  -0.613  -1.361  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.296   0.094  -1.882  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.810  -0.089   0.014  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.675   0.929   0.298  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.283   2.195   0.243  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.356   3.104  -0.319  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.597   3.085   0.464  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.626   2.572  -0.029  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.628   3.628   1.731  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.024   2.496  -0.524  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.019   1.471  -0.254  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.632   0.258   0.011  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.585  -0.834   0.304  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.179  -1.981   0.555  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.027  -0.573   0.301  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.975  -1.545   0.562  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.630  -2.832   0.846  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.315  -1.166   0.523  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.713   0.108   0.242  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.746   1.055  -0.013  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.419   0.720   0.016  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.418   1.781  -0.270  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.832   2.937  -0.522  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.967  -1.038   1.020  0.00  0.00           O+0
HETATM   30  H   UNK     0      -2.858  -1.753   2.866  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.705  -3.122   2.446  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.414  -3.113   1.879  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.948  -1.119   0.503  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.089  -3.525   0.081  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.797  -3.405  -0.398  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.228  -2.230  -2.233  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.137  -2.301  -2.962  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.336  -0.337  -2.062  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.776  -0.555  -2.485  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.106   2.566   1.293  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.533   2.903  -1.402  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.948   4.157  -0.269  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.774   4.617   1.841  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.178   2.509  -1.621  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.406   3.475  -0.237  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.772  -3.248   0.913  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.043  -1.950   0.731  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.774   0.402   0.206  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.036   2.089  -0.248  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   29   33                                             
CONECT    3    2    4   34   35                                             
CONECT    4    3    5    6   36                                             
CONECT    5    4   37                                                       
CONECT    6    4    7    8   38                                             
CONECT    7    6   39                                                       
CONECT    8    6    9   29   17                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   15   40                                             
CONECT   11   10   12   41   42                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   43                                                       
CONECT   15   10   16   44   45                                             
CONECT   16   15   17   27                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   46                                                       
CONECT   23   21   24   47                                                  
CONECT   24   23   25   48                                                  
CONECT   25   24   26   49                                                  
CONECT   26   25   27   20                                                  
CONECT   27   26   28   16                                                  
CONECT   28   27                                                            
CONECT   29    8    2                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

RDKit          3D

49 52  0  0  0  0  0  0  0  0999 V2000
   -2.5381   -2.4857    2.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -1.7721    0.8489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8687   -2.7758   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4090   -2.0676   -1.4650 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3031   -2.7214   -2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840   -0.6132   -1.3609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2964    0.0937   -1.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8104   -0.0890    0.0140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6749    0.9288    0.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829    2.1946    0.2433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3558    3.1042   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5971    3.0854    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6259    2.5716   -0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6275    3.6281    1.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    2.4961   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    1.4711   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.2578    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -0.8340    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1787   -1.9808    0.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272   -0.5730    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753   -1.5451    0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -2.8315    0.8460 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -1.1664    0.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7131    0.1083    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7456    1.0548   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192    0.7198    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4175    1.7807   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8317    2.9373   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670   -1.0376    1.0205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.7526    2.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -3.1222    2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137   -3.1132    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -1.1188    0.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887   -3.5253    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7969   -3.4054   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285   -2.2300   -2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372   -2.3005   -2.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3358   -0.3371   -2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7763   -0.5549   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058    2.5664    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    2.9031   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482    4.1567   -0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7740    4.6174    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    2.5094   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060    3.4747   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -3.2481    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0430   -1.9502    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7740    0.4024    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0359    2.0892   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  8 29  1  0
 29  2  1  0
 17  8  1  0
 26 20  1  0
 27 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  6 38  1  6
  7 39  1  0
 10 40  1  1
 11 41  1  0
 11 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-[(1R,3S,3'r,4's,6'r)-3',4',9-Trihydroxy-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetate	Generator

Chemical Formula

C₂₀H₂₀O₉

Average Mass

404.3710 Da

Monoisotopic Mass

404.11073 Da

IUPAC Name

2-[(1R,3S,3'R,4'S,6'R)-3',4',9-trihydroxy-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetic acid

Traditional Name

(1R,3S,3'R,4'S,6'R)-3',4',9-trihydroxy-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-ylacetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@@H](O)[C@]2(O1)O[C@H](CC(O)=O)CC1=C2C(=O)C2=C(C=CC=C2O)C1=O

InChI Identifier

InChI=1S/C20H20O9/c1-8-5-13(22)19(27)20(28-8)16-11(6-9(29-20)7-14(23)24)17(25)10-3-2-4-12(21)15(10)18(16)26/h2-4,8-9,13,19,21-22,27H,5-7H2,1H3,(H,23,24)/t8-,9+,13+,19-,20-/m1/s1

InChI Key

VNNLNRPAIDMNEB-WPPLHGJESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nocardiopsis sp.	NPAtlas	17877337

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Oxane
Benzenoid
Pyran
Vinylogous acid
Secondary alcohol
1,2-diol
Ketone
Polyol
Acetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Alcohol
Aldehyde
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.24	ALOGPS
logP	0.85	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.26 m³·mol⁻¹	ChemAxon
Polarizability	38.94 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

NPAtlas ID

NPA010162

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23289502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23631017

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

He J, Roemer E, Lange C, Huang X, Maier A, Kelter G, Jiang Y, Xu LH, Menzel KD, Grabley S, Fiebig HH, Jiang CL, Sattler I: Structure, derivatization, and antitumor activity of new griseusins from Nocardiopsis sp. J Med Chem. 2007 Oct 18;50(21):5168-75. doi: 10.1021/jm070170n. Epub 2007 Sep 18. [PubMed:17877337 ]

Showing NP-Card for Epi-deacetylgriseusin B (NP0007274)

MOL for NP0007274 (Epi-deacetylgriseusin B)

3D MOL for NP0007274 (Epi-deacetylgriseusin B)

3D SDF for NP0007274 (Epi-deacetylgriseusin B)

3D-SDF for NP0007274 (Epi-deacetylgriseusin B)

PDB for NP0007274 (Epi-deacetylgriseusin B)

3D PDB for NP0007274 (Epi-deacetylgriseusin B)

SMILES for NP0007274 (Epi-deacetylgriseusin B)

INCHI for NP0007274 (Epi-deacetylgriseusin B)

Structure for NP0007274 (Epi-deacetylgriseusin B)

3D Structure for NP0007274 (Epi-deacetylgriseusin B)