NP-MRD: Showing NP-Card for (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate (NP0214445)

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Record Information

Version

2.0

Created at

2022-09-05 13:44:45 UTC

Updated at

2022-09-05 13:44:45 UTC

NP-MRD ID

NP0214445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate

Description

Butylshikonin 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). (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate is found in Arnebia hispidissima and Lithospermum erythrorhizon. (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate was first documented in 2009 (PMID: 19027226). Based on a literature review a small amount of articles have been published on butylshikonin (PMID: 28929657) (PMID: 25124618).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215442D          

 26 27  0  0  1  0            999 V2000
    3.7638   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4763   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  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
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
   -2.9027   -3.4240    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -2.7302   -0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017   -1.2506   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -0.5894    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962   -0.8479    1.6271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    0.2622   -0.1036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    0.8602    0.7378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2902    2.3729    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053    2.8771    1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    3.6152    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    4.1138    0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022    3.9855   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.3893    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842    1.2255   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4170    0.7705   -0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2865    1.6199   -0.7095 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7456   -0.6364   -0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815   -1.1050   -0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9943   -0.2575   -1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2573   -2.4783   -0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509   -3.3474   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134   -2.8868   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -3.7586    0.1135 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7406   -1.5457   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -1.0275    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -1.8713    0.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -3.2743    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0069   -3.1579    1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -4.5273    0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168   -2.9550   -1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -3.1524   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -1.1743    0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054   -0.8144   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891    0.5408    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4648    2.7514    1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    2.7756   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9574    2.6350    2.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966    5.1333    1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3367    4.1548   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716    3.4889    1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    3.1092   -1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6068    4.7513   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    4.4358   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    2.2837    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1483    0.6851   -1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -2.8516   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482   -4.4208   -0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -4.7524    0.0739 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 25 13  1  0
 24 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 14 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
M  END


  Mrv1652309052215442D          

 26 27  0  0  1  0            999 V2000
    3.7638   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4763   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  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
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0214445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-4-5-17(24)26-16(9-6-11(2)3)12-10-15(23)18-13(21)7-8-14(22)19(18)20(12)25/h6-8,10,16,21-22H,4-5,9H2,1-3H3/t16-/m1/s1

> <INCHI_KEY>
FMXUZLUFNDEQPM-MRXNPFEDSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.172687516219966

> <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 butanoate

> <JCHEM_LOGP>
4.597870927000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160495170123887

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489931525426062

> <JCHEM_PKA_STRONGEST_BASIC>
-5.564946698480999

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
98.19959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.026  -0.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.566  -0.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.876  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.646  -0.976   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.646  -3.644   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.186  -3.644   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.956  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.496  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.266  -0.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.806  -0.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.496   0.357   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.956  -4.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.496  -4.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.266  -6.311   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      17.806  -6.311   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.496  -7.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.266  -8.978   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.806  -8.978   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.496 -10.312   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.956 -10.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.186  -8.978   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.646  -8.978   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.956  -7.645   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.186  -6.311   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.646  -6.311   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24   13   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3900 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C20H22O6/c1-4-5-17(24)26-16(9-6-11(2)3)12-10-15(23)18-13(21)7-8-14(22)19(18)20(12)25/h6-8,10,16,21-22H,4-5,9H2,1-3H3/t16-/m1/s1

InChI Key

FMXUZLUFNDEQPM-MRXNPFEDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Arnebia hispidissima	LOTUS Database	35616633
Lithospermum erythrorhizon	LOTUS Database	35616633

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	4.6	ChemAxon
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	98.2 m³·mol⁻¹	ChemAxon
Polarizability	37.17 Å³	ChemAxon
Number of Rings	2	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

8265303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10089766

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao WW, Wu ZM, Wu X, Zhao HY, Chen XQ: [Determination of five naphthaquinones in Arnebia euchroma by quantitative analysis multi-components with single-marker]. Zhongguo Zhong Yao Za Zhi. 2016 Oct;41(20):3792-3797. doi: 10.4268/cjcmm20162014. [PubMed:28929657 ]
Wang HB, Ma XQ: Activation of JNK/p38 pathway is responsible for alpha-methyl-n-butylshikonin induced mitochondria-dependent apoptosis in SW620 human colorectal cancer cells. Asian Pac J Cancer Prev. 2014;15(15):6321-6. doi: 10.7314/apjcp.2014.15.15.6321. [PubMed:25124618 ]
Xuan Y, Hu X: Naturally-occurring shikonin analogues--a class of necroptotic inducers that circumvent cancer drug resistance. Cancer Lett. 2009 Feb 18;274(2):233-42. doi: 10.1016/j.canlet.2008.09.029. Epub 2008 Nov 21. [PubMed:19027226 ]
LOTUS database [Link]

Showing NP-Card for (1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate (NP0214445)

MOL for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

3D MOL for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

3D SDF for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

3D-SDF for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

PDB for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

3D PDB for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

SMILES for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

INCHI for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

Structure for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)

3D Structure for NP0214445 ((1r)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl butanoate)