NP-MRD: Showing NP-Card for alpha-methylbutyrylshikonin (NP0036682)

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Record Information

Version

2.0

Created at

2021-06-20 19:47:28 UTC

Updated at

2021-06-30 00:08:27 UTC

NP-MRD ID

NP0036682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-methylbutyrylshikonin

Provided By

JEOL Database JEOL Logo

Description

ZINC6412269 belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). alpha-methylbutyrylshikonin is found in Onosma paniculata. alpha-methylbutyrylshikonin was first documented in 2012 (Kretschmer, N., et al.). Based on a literature review very few articles have been published on ZINC6412269.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121473D          

 51 52  0  0  0  0            999 V2000
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   -2.8169   -5.0005    0.0200 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121473D          

 51 52  0  0  0  0            999 V2000
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   -0.0339   -0.7799    1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    2.4537    3.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    5.4793    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027    5.8869   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2173    3.4950   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 19 18  2  0  0  0  0
 10 11  2  3  0  0  0
 22 21  2  0  0  0  0
 11 12  1  0  0  0  0
 25 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 22  1  0  0  0  0
 19 20  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 15  1  0  0  0  0
 11 13  1  0  0  0  0
 15 14  2  0  0  0  0
  8  7  1  0  0  0  0
 14 26  1  0  0  0  0
  7  5  1  0  0  0  0
 25 18  1  0  0  0  0
  5  3  1  0  0  0  0
 14  8  1  0  0  0  0
  5  6  2  0  0  0  0
  3  2  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 21 19  1  0  0  0  0
  3  4  1  0  0  0  0
 22 50  1  0  0  0  0
 21 49  1  0  0  0  0
 15 47  1  0  0  0  0
  8 37  1  6  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
 10 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 24 51  1  0  0  0  0
 20 48  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
  3 33  1  1  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(C(=O)C2=C(O[H])C([H])=C1[H])[C@]([H])(OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O6/c1-5-12(4)21(26)27-17(9-6-11(2)3)13-10-16(24)18-14(22)7-8-15(23)19(18)20(13)25/h6-8,10,12,17,22-23H,5,9H2,1-4H3/t12-,17+/m0/s1

> <INCHI_KEY>
ODQATBANLZCROD-YVEFUNNKSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.417

> <EXACT_MASS>
372.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.143904223784695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (2S)-2-methylbutanoate

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
5.140857205333333

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160463063646738

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489928457408144

> <JCHEM_PKA_STRONGEST_BASIC>
-5.564946699235706

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
102.77409999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (2S)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
   -1.4112   -5.3355   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169   -5.0005    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -3.6244    0.6927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2704   -3.3946    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -2.5202   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895   -2.3270   -1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -1.7823    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1769   -0.6986   -0.8105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3433   -1.2586   -1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852   -1.8444   -1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -1.3608   -1.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -2.0977   -1.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -0.0942   -2.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205    0.3489   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    0.1619    1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223    1.1996    1.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429    0.9907    3.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    2.4867    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081    3.4890    1.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459    3.3439    3.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400    4.7081    1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    4.9363    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813    3.9446   -0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    4.2534   -1.8760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452    2.7127    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423    1.6654   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335    1.8968   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6925   -5.2922    0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880   -6.3474   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -4.6448   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059   -5.0523   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1313   -5.7728    0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -3.5717    1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675   -3.4560    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266   -2.4020    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4746   -4.1399    2.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.2323   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -0.4865   -2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998   -2.0660   -2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950   -2.7778   -1.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.4626   -0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1768   -3.0149   -0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827   -2.3772   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032    0.5883   -1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    0.4456   -2.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.3207   -3.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -0.7799    1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    2.4537    3.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    5.4793    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027    5.8869   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2173    3.4950   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 19 18  2  0
 10 11  2  3
 22 21  2  0
 11 12  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
 19 20  1  0
 25 26  1  0
 26 27  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 11 13  1  0
 15 14  2  0
  8  7  1  0
 14 26  1  0
  7  5  1  0
 25 18  1  0
  5  3  1  0
 14  8  1  0
  5  6  2  0
  3  2  1  0
  8  9  1  0
  2  1  1  0
 21 19  1  0
  3  4  1  0
 22 50  1  0
 21 49  1  0
 15 47  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 24 51  1  0
 20 48  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
  3 33  1  1
  2 31  1  0
  2 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.411  -5.335  -0.462  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.817  -5.000   0.020  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.897  -3.624   0.693  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.270  -3.395   1.319  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.632  -2.520  -0.313  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.289  -2.327  -1.325  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.555  -1.782   0.073  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.177  -0.699  -0.811  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.343  -1.259  -1.991  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.985  -1.844  -1.567  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.221  -1.361  -1.803  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.438  -2.098  -1.303  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.538  -0.094  -2.551  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.421   0.349  -0.012  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.073   0.162   1.221  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.822   1.200   1.946  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.243   0.991   3.079  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.062   2.487   1.278  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.808   3.489   1.915  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.346   3.344   3.165  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.040   4.708   1.283  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.526   4.936   0.008  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.781   3.945  -0.627  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.313   4.253  -1.876  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.545   2.713   0.002  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.242   1.665  -0.677  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.734   1.897  -1.779  0.00  0.00           O+0
HETATM   28  H   UNK     0      -0.693  -5.292   0.363  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.388  -6.347  -0.879  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.082  -4.645  -1.244  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.506  -5.052  -0.832  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.131  -5.773   0.732  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.146  -3.572   1.491  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.067  -3.456   0.569  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.327  -2.402   1.779  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.475  -4.140   2.094  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.093  -0.232  -1.196  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.214  -0.487  -2.754  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.900  -2.066  -2.482  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.895  -2.778  -1.010  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.010  -1.463  -0.619  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.177  -3.015  -0.765  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.083  -2.377  -2.142  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.103   0.588  -1.907  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.653   0.446  -2.893  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.146  -0.321  -3.432  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.034  -0.780   1.749  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.108   2.454   3.510  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.620   5.479   1.784  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.703   5.887  -0.489  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.217   3.495  -2.211  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1   31   32                                             
CONECT    3    5    2    4   33                                             
CONECT    4    3   34   35   36                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    7   14    9   37                                             
CONECT    9   10    8   38   39                                             
CONECT   10    9   11   40                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   41   42   43                                             
CONECT   13   11   44   45   46                                             
CONECT   14   15   26    8                                                  
CONECT   15   16   14   47                                                  
CONECT   16   18   17   15                                                  
CONECT   17   16                                                            
CONECT   18   19   16   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   48                                                       
CONECT   21   22   19   49                                                  
CONECT   22   21   23   50                                                  
CONECT   23   25   24   22                                                  
CONECT   24   23   51                                                       
CONECT   25   23   26   18                                                  
CONECT   26   25   27   14                                                  
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   15                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  104    0
END

RDKit          3D

51 52  0  0  0  0  0  0  0  0999 V2000
   -1.4112   -5.3355   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169   -5.0005    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -3.6244    0.6927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2704   -3.3946    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -2.5202   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895   -2.3270   -1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -1.7823    0.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1769   -0.6986   -0.8105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3433   -1.2586   -1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852   -1.8444   -1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -1.3608   -1.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -2.0977   -1.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -0.0942   -2.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205    0.3489   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    0.1619    1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223    1.1996    1.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429    0.9907    3.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    2.4867    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081    3.4890    1.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459    3.3439    3.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400    4.7081    1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    4.9363    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813    3.9446   -0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    4.2534   -1.8760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452    2.7127    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423    1.6654   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335    1.8968   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6925   -5.2922    0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880   -6.3474   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817   -4.6448   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059   -5.0523   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1313   -5.7728    0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -3.5717    1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675   -3.4560    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266   -2.4020    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4746   -4.1399    2.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.2323   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -0.4865   -2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998   -2.0660   -2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950   -2.7778   -1.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.4626   -0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1768   -3.0149   -0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827   -2.3772   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032    0.5883   -1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    0.4456   -2.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.3207   -3.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -0.7799    1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1076    2.4537    3.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    5.4793    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027    5.8869   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2173    3.4950   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 19 18  2  0
 10 11  2  3
 22 21  2  0
 11 12  1  0
 25 23  2  0
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 11 13  1  0
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  8  7  1  0
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  7  5  1  0
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  5  3  1  0
 14  8  1  0
  5  6  2  0
  3  2  1  0
  8  9  1  0
  2  1  1  0
 21 19  1  0
  3  4  1  0
 22 50  1  0
 21 49  1  0
 15 47  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
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 12 43  1  0
 24 51  1  0
 20 48  1  0
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  3 33  1  1
  2 31  1  0
  2 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₆

Average Mass

372.4170 Da

Monoisotopic Mass

372.15729 Da

IUPAC Name

(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (2S)-2-methylbutanoate

Traditional Name

(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl (2S)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)C([H])=C(C(=O)C2=C(O[H])C([H])=C1[H])[C@]([H])(OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H24O6/c1-5-12(4)21(26)27-17(9-6-11(2)3)13-10-16(24)18-14(22)7-8-15(23)19(18)20(13)25/h6-8,10,12,17,22-23H,5,9H2,1-4H3/t12-,17+/m0/s1

InChI Key

ODQATBANLZCROD-YVEFUNNKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Onosma paniculata	JEOL database	Kretschmer, N., et al, J. Nat. Prod. 75, 865 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Vinylogous acid
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	3.68	ALOGPS
logP	5.14	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.77 m³·mol⁻¹	ChemAxon
Polarizability	39.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92297005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kretschmer, N., et al. (2012). Kretschmer, N., et al, J. Nat. Prod. 75, 865 (2012). J. Nat. Prod..

Showing NP-Card for alpha-methylbutyrylshikonin (NP0036682)

MOL for NP0036682 (alpha-methylbutyrylshikonin)

3D MOL for NP0036682 (alpha-methylbutyrylshikonin)

3D SDF for NP0036682 (alpha-methylbutyrylshikonin)

3D-SDF for NP0036682 (alpha-methylbutyrylshikonin)

PDB for NP0036682 (alpha-methylbutyrylshikonin)

3D PDB for NP0036682 (alpha-methylbutyrylshikonin)

SMILES for NP0036682 (alpha-methylbutyrylshikonin)

INCHI for NP0036682 (alpha-methylbutyrylshikonin)

Structure for NP0036682 (alpha-methylbutyrylshikonin)

3D Structure for NP0036682 (alpha-methylbutyrylshikonin)