NP-MRD: Showing NP-Card for (1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate (NP0145039)

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Record Information

Version

2.0

Created at

2022-09-02 00:08:47 UTC

Updated at

2022-09-02 00:08:47 UTC

NP-MRD ID

NP0145039

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Isovalerylalkannin 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). (1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate is found in Arnebia decumbens, Arnebia euchroma, Arnebia hispidissima and Lithospermum erythrorhizon. (1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate was first documented in 2006 (PMID: 17080496). Based on a literature review a small amount of articles have been published on isovalerylalkannin (PMID: 35709606) (PMID: 30449173) (PMID: 27061885) (PMID: 25973485).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202082D          

 27 28  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    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 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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
    0.9806    3.9561    2.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    3.5173    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1054    4.1228   -0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519    2.5781    0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047    2.1578   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7757    0.7317   -0.7319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5256   -0.0603    0.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -0.7662   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0154   -0.6831   -1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4368   -1.5891    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6047   -2.2177    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3704   -3.0468    1.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586   -3.0986   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5841    0.1945   -0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.1887   -2.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3600   -0.7241   -2.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931   -1.0629   -3.4629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002   -0.8690   -1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5697   -1.3766   -1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0110   -1.7679   -2.6349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4265   -1.4892   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0341   -1.1138    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -0.5946    1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -0.2398    2.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -0.4781    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160    0.0545    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1510    0.4017    1.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364    3.5720    3.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0262    3.6049    2.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869    5.0593    2.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    4.8057    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    3.2789   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3208    4.6807   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    2.1918    1.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9998    2.4636   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    2.8392   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197    0.6217   -1.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7510   -1.0353    1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744   -2.4344    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2651   -1.4127   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0235   -4.0895    1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4275   -3.0376    0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2932   -2.5697    2.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0622   -3.2677   -1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4647   -2.6457   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6511   -4.0898   -1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676   -0.1009   -2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6998   -1.8188   -3.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4157   -1.8906   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6934   -1.1973    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6565    0.1239    2.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 26 14  1  0
 25 18  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 11 40  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 10 38  1  0
 10 39  1  0
  6 37  1  6
  5 35  1  0
  5 36  1  0
  4 34  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
 15 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
M  END


  Mrv1652309022202082D          

 27 28  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    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 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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0145039

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,10,12,17,22-23H,8-9H2,1-4H3/t17-/m0/s1

> <INCHI_KEY>
UTOUNDHZJFIVPK-KRWDZBQOSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.417

> <EXACT_MASS>
372.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.45992426129019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
4.884890023333333

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160494636427941

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489931475306177

> <JCHEM_PKA_STRONGEST_BASIC>
-5.564946698486197

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
102.74819999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.74e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   0.000   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                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   14   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₆

Average Mass

372.4170 Da

Monoisotopic Mass

372.15729 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H24O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,10,12,17,22-23H,8-9H2,1-4H3/t17-/m0/s1

InChI Key

UTOUNDHZJFIVPK-KRWDZBQOSA-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
Arnebia euchroma	LOTUS Database	35616633
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	3.18	ALOGPS
logP	4.88	ChemAxon
logS	-4	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	102.75 m³·mol⁻¹	ChemAxon
Polarizability	39.46 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

4477203

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang J, He JM, Mu Q: Relayed chromatography - Countercurrent chromatography in series with liquid chromatography for the separation of natural products. J Chromatogr A. 2022 Aug 2;1676:463205. doi: 10.1016/j.chroma.2022.463205. Epub 2022 Jun 9. [PubMed:35709606 ]
Yuzbasioglu Baran M, Guvenalp Z, Saracoglu I, Kazaz C, Salih B, Demirezer LO, Kuruuzum-Uz A: Cytotoxic naphthoquinones from Arnebia densiflora (Nordm.) Ledeb and determining new apoptosis inducers. Nat Prod Res. 2020 Jun;34(12):1669-1677. doi: 10.1080/14786419.2018.1525714. Epub 2018 Nov 17. [PubMed:30449173 ]
Zhang M, Zhao H, Zhao Z, Yan H, Lv R, Cui L, Yuan J, Wang D, Geng Y, Liu D, Wang X: Rapid screening, identification, and purification of neuraminidase inhibitors from Lithospermum erythrorhizon Sieb.et Zucc. by ultrafiltration with HPLC-ESI-TOF-MS combined with semipreparative HPLC. J Sep Sci. 2016 Jun;39(11):2097-104. doi: 10.1002/jssc.201600087. Epub 2016 Apr 28. [PubMed:27061885 ]
Yuzbasioglu M, Kuruuzum-Uz A, Guvenalp Z, Simon A, Toth G, Harput US, Kazaz C, Bilgili B, Duman H, Saracoglu I, Demirezer LO: Cytotoxic compounds from endemic Arnebia purpurea. Nat Prod Commun. 2015 Apr;10(4):595-6. [PubMed:25973485 ]
Assimopoulou AN, Karapanagiotis I, Vasiliou A, Kokkini S, Papageorgiou VP: Analysis of alkannin derivatives from Alkanna species by high-performance liquid chromatography/photodiode array/mass spectrometry. Biomed Chromatogr. 2006 Dec;20(12):1359-74. doi: 10.1002/bmc.705. [PubMed:17080496 ]
LOTUS database [Link]

Showing NP-Card for (1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate (NP0145039)

MOL for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

3D MOL for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

3D SDF for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

3D-SDF for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

PDB for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

3D PDB for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

SMILES for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

INCHI for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

Structure for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)

3D Structure for NP0145039 ((1s)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate)