NP-MRD: Showing NP-Card for 5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate (NP0328173)

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Record Information

Version

2.0

Created at

2022-09-12 11:24:31 UTC

Updated at

2022-09-12 11:24:32 UTC

NP-MRD ID

NP0328173

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate

Description

Shikonin acetate 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). 5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate is found in Arnebia decumbens. Based on a literature review very few articles have been published on shikonin acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213242D          

 25 26  0  0  1  0            999 V2000
    0.1501    0.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -0.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9626   -2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229   -1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532   -1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  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
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
   -1.6473    3.5805   -2.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8789    2.9200   -1.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1154    3.5856   -0.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0149    1.5925   -1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717    0.8208   -0.1577 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1040    0.8893   -0.3789 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4732    0.4044   -1.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9111    0.1494    0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672    0.3686    0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2499   -0.5789    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435   -2.0137    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951   -0.2179    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887    1.1741    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    0.9535    1.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9957    1.8219    1.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8442   -0.3119    0.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -0.7388    1.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7753    0.0357    2.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5965   -1.9371    1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -2.7007    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285   -2.2798   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8933   -3.0460   -1.2367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -1.0753    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8108   -0.5749   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631   -1.3468   -1.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    3.0980   -3.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7414    3.4573   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    4.6513   -2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    1.9432   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -0.4154   -1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7113    0.4533    1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7266   -0.9420    0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368    1.4101    0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3318   -2.2466   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7620   -2.6532    0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1710   -2.3044    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7857    0.6498   -0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244    0.0472    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125   -1.0605   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3048    0.4089    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755    2.1504    1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6568   -0.1984    2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5413   -2.3410    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2166   -3.6556   -0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3013   -3.9266   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 10  9  2  3
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
  5  4  1  6
  4  2  1  0
  2  1  1  0
  2  3  2  0
 24  5  1  0
 23 16  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
  9 33  1  0
  8 31  1  0
  8 32  1  0
  6 29  1  6
  7 30  1  0
 13 40  1  0
 13 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652309122213242D          

 25 26  0  0  1  0            999 V2000
    0.1501    0.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -0.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9626   -2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229   -1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532   -1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  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
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0328173

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O7/c1-9(2)4-7-14(23)18(25-10(3)19)8-13(22)15-11(20)5-6-12(21)16(15)17(18)24/h4-6,14,20-21,23H,7-8H2,1-3H3/t14-,18?/m1/s1

> <INCHI_KEY>
MNGVKFABFGGTBC-IKJXHCRLSA-N

> <FORMULA>
C18H20O7

> <MOLECULAR_WEIGHT>
348.351

> <EXACT_MASS>
348.120902984

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.033505498025804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl acetate

> <JCHEM_LOGP>
2.651115905000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.766093862411395

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.331307167112566

> <JCHEM_PKA_STRONGEST_BASIC>
-3.36496104812434

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
89.36509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3H-naphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.280   0.584   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.226  -0.328   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.183  -2.043   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.797  -4.937   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.710  -4.025   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.700  -2.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.216  -3.112   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.743  -4.559   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.206  -1.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13   24                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23    5   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
Shikonin acetic acid	Generator

Chemical Formula

C₁₈H₂₀O₇

Average Mass

348.3510 Da

Monoisotopic Mass

348.12090 Da

IUPAC Name

5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl acetate

Traditional Name

5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3H-naphthalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H20O7/c1-9(2)4-7-14(23)18(25-10(3)19)8-13(22)15-11(20)5-6-12(21)16(15)17(18)24/h4-6,14,20-21,23H,7-8H2,1-3H3/t14-,18?/m1/s1

InChI Key

MNGVKFABFGGTBC-IKJXHCRLSA-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 decumbens	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
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Alpha-acyloxy ketone
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.65	ChemAxon
pKa (Strongest Acidic)	8.33	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.37 m³·mol⁻¹	ChemAxon
Polarizability	35.03 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

67169350

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129650338

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate (NP0328173)

MOL for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

3D MOL for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

3D SDF for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

3D-SDF for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

PDB for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

3D PDB for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

SMILES for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

INCHI for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

Structure for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)

3D Structure for NP0328173 (5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate)