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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:45 UTC

Update Date

2022-03-07 02:52:36 UTC

HMDB ID

HMDB0030579

Secondary Accession Numbers

HMDB30579

Metabolite Identification

Common Name

C.I. Natural Red 20

Description

C.I. Natural Red 20 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). Based on a literature review very few articles have been published on C.I. Natural Red 20.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030579
     RDKit          3D
C.I. Natural Red 20
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.0436    1.6487   -1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    0.3332   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -0.4191    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -0.1768   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0063   -1.4756   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645   -1.5073    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268   -0.7493    2.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -1.1232    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117   -2.0720    0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076   -1.8112    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887   -2.7894    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -0.4502   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -0.1299   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4224   -1.0662   -0.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8170    1.2011   -0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8903    2.1868   -0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885    1.8825   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762    2.9187   -0.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    0.5677    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    0.2365    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0549    1.2283    0.4629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    2.2052   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7773    1.5404   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    2.2274   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046    0.2519    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -0.6951    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622   -1.2895   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.4368   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263   -2.1433   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670   -1.9784    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -2.5598    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5416    0.1736    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -3.1247    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3726   -2.0119   -0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8487    1.4274   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1734    3.2302   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    3.8761   -0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20  8  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
M  END


  Mrv0541 05061305212D          

 21 22  0  0  0  0            999 V2000
    6.4302    3.7125    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
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    0.7145    2.0625    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
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434    2.0625    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
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030579

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3

> <INCHI_KEY>
NEZONWMXZKDMKF-UHFFFAOYSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.2952

> <EXACT_MASS>
288.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.796748179154434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
3.011641004666666

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.890235896794804

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.60373930011847

> <JCHEM_PKA_STRONGEST_BASIC>
-3.105504600562978

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
79.82019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030579
     RDKit          3D
C.I. Natural Red 20
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.0436    1.6487   -1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    0.3332   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -0.4191    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -0.1768   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0063   -1.4756   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645   -1.5073    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268   -0.7493    2.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -1.1232    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117   -2.0720    0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076   -1.8112    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887   -2.7894    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -0.4502   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -0.1299   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4224   -1.0662   -0.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8170    1.2011   -0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8903    2.1868   -0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885    1.8825   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762    2.9187   -0.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    0.5677    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    0.2365    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0549    1.2283    0.4629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    2.2052   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7773    1.5404   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    2.2274   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046    0.2519    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -0.6951    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622   -1.2895   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.4368   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263   -2.1433   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670   -1.9784    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -2.5598    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5416    0.1736    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -3.1247    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3726   -2.0119   -0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8487    1.4274   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1734    3.2302   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    3.8761   -0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20  8  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    8                                                       
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7    9   13                                                       
CONECT    8    1    2    3                                                  
CONECT    9    7   10   16                                                  
CONECT   10    4    9   17                                                  
CONECT   11    5   14   18                                                  
CONECT   12    6   15   19                                                  
CONECT   13    7   14   20                                                  
CONECT   14   11   13   15                                                  
CONECT   15   12   14   16                                                  
CONECT   16    9   15   21                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0258273
HETATM    1  C1  UNL     1      -3.839  -1.546  -1.694  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.563  -0.334  -0.890  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.694   0.467  -0.346  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.302   0.040  -0.654  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.965   1.236   0.137  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.143   0.904   1.361  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.862   0.042   2.165  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.193   0.373   1.015  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.530  -0.829   1.415  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.826  -1.432   1.120  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.048  -2.583   1.547  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.829  -0.716   0.352  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.057  -1.290   0.074  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.414  -2.530   0.482  1.00  0.00           O  
HETATM   15  C12 UNL     1       4.972  -0.526  -0.678  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.649   0.721  -1.104  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.406   1.314  -0.827  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.179   2.563  -1.297  1.00  0.00           O  
HETATM   19  C15 UNL     1       2.506   0.580  -0.096  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.183   1.112   0.243  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.886   2.272  -0.155  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.660  -2.166  -1.280  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.931  -2.196  -1.666  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.992  -1.311  -2.776  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.587   0.601   0.769  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.783   1.438  -0.865  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.646  -0.076  -0.510  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.483  -0.547  -1.054  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.911   1.720   0.452  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.416   2.003  -0.455  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.058   1.870   1.938  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.394  -0.009   3.040  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.165  -1.431   1.996  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.973  -3.215   0.988  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.926  -1.006  -0.878  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.364   1.290  -1.678  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.452   3.196  -1.266  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    4
CONECT    3   25   26   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7    8   31
CONECT    7   32
CONECT    8    9    9   20
CONECT    9   10   33
CONECT   10   11   11   12
CONECT   12   13   13   19
CONECT   13   14   15
CONECT   14   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   19   19
CONECT   18   37
CONECT   19   20
CONECT   20   21   21
END

HMDB0030579
     RDKit          3D
C.I. Natural Red 20
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.0436    1.6487   -1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    0.3332   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -0.4191    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -0.1768   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0063   -1.4756   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645   -1.5073    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268   -0.7493    2.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -1.1232    0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117   -2.0720    0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076   -1.8112    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887   -2.7894    0.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -0.4502   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -0.1299   -0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4224   -1.0662   -0.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8170    1.2011   -0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8903    2.1868   -0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885    1.8825   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762    2.9187   -0.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    0.5677    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8296    0.2365    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0549    1.2283    0.4629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    2.2052   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7773    1.5404   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    2.2274   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046    0.2519    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -0.6951    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622   -1.2895   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.4368   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263   -2.1433   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670   -1.9784    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -2.5598    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5416    0.1736    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -3.1247    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3726   -2.0119   -0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8487    1.4274   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1734    3.2302   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    3.8761   -0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20  8  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  9 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alkanet extract	HMDB
Alkanna red	HMDB
Alkannin	HMDB
Anchusa acid	HMDB
Anchusin	HMDB
C.I. 75530	HMDB
2-((1R)-1-Hydroxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone	MeSH
5,8-Dihydroxy-2-((1R)-1-hydroxy-4-methyl-3-penten-1-yl)-1,4-naphthalenedione	MeSH
Isoarnebin 4	MeSH
Shikonin, (+)-isomer	MeSH

Chemical Formula

C₁₆H₁₆O₅

Average Molecular Weight

288.2952

Monoisotopic Molecular Weight

288.099773622

IUPAC Name

5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

Traditional Name

5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione

CAS Registry Number

517-88-4

SMILES

CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3

InChI Key

NEZONWMXZKDMKF-UHFFFAOYSA-N

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
Vinylogous acid
Ketone
Secondary alcohol
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

a secondary metabolite (CPD-9322 )
a quinone (CPD-9322 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	116 - 117 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	2.19	ALOGPS
logP	3.01	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.82 m³·mol⁻¹	ChemAxon
Polarizability	29.8 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.492	31661259
DarkChem	[M-H]-	165.072	31661259
DeepCCS	[M+H]+	166.752	30932474
DeepCCS	[M-H]-	164.394	30932474
DeepCCS	[M-2H]-	197.28	30932474
DeepCCS	[M+Na]+	172.846	30932474
AllCCS	[M+H]+	167.1	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	169.0	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.04 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2397 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
C.I. Natural Red 20	CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O	3976.5	Standard polar	33892256
C.I. Natural Red 20	CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O	2286.8	Standard non polar	33892256
C.I. Natural Red 20	CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O	2522.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
C.I. Natural Red 20,1TMS,isomer #1	CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O	2478.9	Semi standard non polar	33892256
C.I. Natural Red 20,1TMS,isomer #2	CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O	2609.4	Semi standard non polar	33892256
C.I. Natural Red 20,1TMS,isomer #3	CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O	2591.5	Semi standard non polar	33892256
C.I. Natural Red 20,2TMS,isomer #1	CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O)=C2C1=O	2538.0	Semi standard non polar	33892256
C.I. Natural Red 20,2TMS,isomer #2	CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C)=C2C1=O	2526.9	Semi standard non polar	33892256
C.I. Natural Red 20,2TMS,isomer #3	CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O	2591.4	Semi standard non polar	33892256
C.I. Natural Red 20,3TMS,isomer #1	CC(C)=CCC(O[Si](C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2C1=O	2572.6	Semi standard non polar	33892256
C.I. Natural Red 20,1TBDMS,isomer #1	CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O	2754.9	Semi standard non polar	33892256
C.I. Natural Red 20,1TBDMS,isomer #2	CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O	2855.1	Semi standard non polar	33892256
C.I. Natural Red 20,1TBDMS,isomer #3	CC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2842.5	Semi standard non polar	33892256
C.I. Natural Red 20,2TBDMS,isomer #1	CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C2C1=O	3041.3	Semi standard non polar	33892256
C.I. Natural Red 20,2TBDMS,isomer #2	CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3035.6	Semi standard non polar	33892256
C.I. Natural Red 20,2TBDMS,isomer #3	CC(C)=CCC(O)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3073.5	Semi standard non polar	33892256
C.I. Natural Red 20,3TBDMS,isomer #1	CC(C)=CCC(O[Si](C)(C)C(C)(C)C)C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3263.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ml-9280000000-b0844b9158a9ed8540c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (3 TMS) - 70eV, Positive	splash10-01yc-9400800000-80ea5d873c7acc0809bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - C.I. Natural Red 20 GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Positive-QTOF	splash10-00dr-0090000000-075012fc8e371dc2176e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Positive-QTOF	splash10-0fy9-3690000000-91f11e32821de969fc96	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Positive-QTOF	splash10-0gbc-9230000000-192f49a494c02eaf64b3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Negative-QTOF	splash10-000i-0090000000-d06cd6d33d99ce2f26d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Negative-QTOF	splash10-000i-2790000000-649136aee6eabbfaaf17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Negative-QTOF	splash10-000i-2900000000-bbd3966288658c0b712f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Negative-QTOF	splash10-000i-0090000000-1b01e1b5bd30ed06ec25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Negative-QTOF	splash10-000i-0390000000-6df930f27a9fb74ab9f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Negative-QTOF	splash10-000i-4940000000-69c7d5eecdd1133dee73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 10V, Positive-QTOF	splash10-000i-0190000000-cbace8aa536e09d6a157	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 20V, Positive-QTOF	splash10-000m-1690000000-7b5921dde568b56f4d51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - C.I. Natural Red 20 40V, Positive-QTOF	splash10-0a4l-8960000000-5d996db7d5d10d3d385c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002470

KNApSAcK ID

Not Available

Chemspider ID

5019

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for C.I. Natural Red 20 (HMDB0030579)

MOL for HMDB0030579 (C.I. Natural Red 20)

3D MOL for HMDB0030579 (C.I. Natural Red 20)

3D SDF for HMDB0030579 (C.I. Natural Red 20)

3D-SDF for HMDB0030579 (C.I. Natural Red 20)

PDB for HMDB0030579 (C.I. Natural Red 20)

3D PDB for HMDB0030579 (C.I. Natural Red 20)

SMILES for HMDB0030579 (C.I. Natural Red 20)

INCHI for HMDB0030579 (C.I. Natural Red 20)

Structure for HMDB0030579 (C.I. Natural Red 20)

3D Structure for HMDB0030579 (C.I. Natural Red 20)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra