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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:08 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030643

Secondary Accession Numbers

HMDB30643

Metabolite Identification

Common Name

Blighinone

Description

Blighinone belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. Based on a literature review a significant number of articles have been published on Blighinone.

Structure

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

HMDB0030643
     RDKit          3D
Blighinone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.4511   -1.9954    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787   -1.1700   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015   -1.4603   -1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -1.5887   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082   -2.8026   -0.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -0.6514   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -1.1242   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612   -2.4430   -0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975   -0.2833    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714   -0.7433    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586    0.0960    0.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -2.0441    0.0808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7597    1.0228    0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    1.5299    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122    2.8373    0.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.6766    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330    1.1248    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943    0.2574   -0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.7663   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -0.0627   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434    2.1245   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6887    2.9300    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    2.4915    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547    3.3412    0.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807   -1.4487    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9580   -2.9837    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4540   -2.1714   -0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -2.3781   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9942   -3.0581   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -2.2924   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801    1.6611    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022    3.4040    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942    2.4732   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    3.9649    0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  2  1  0
 16  6  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  8 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 21 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061305242D          

 24 26  0  0  0  0            999 V2000
   -0.6382   -1.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190    1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4315    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2810    1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1940    1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4560    1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4560   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1940   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2810   -0.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815   -1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    1.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4315   -1.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435    1.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935   -1.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4560   -1.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310    1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310   -0.3414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -1.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 16  1  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17  6  2  0  0  0  0
 18  7  2  0  0  0  0
 19  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 15  2  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030643

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(O)C(=O)C2=C(O)C(=CC(O)=C2C2=C1C(=O)C=CC2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O8/c1-16(24)12-7(18)3-2-6(17)10(12)9-8(19)4-5(15(22)23)13(20)11(9)14(16)21/h2-4,19-20,24H,1H3,(H,22,23)

> <INCHI_KEY>
YFUQJMOETZJFHO-UHFFFAOYSA-N

> <FORMULA>
C16H10O8

> <MOLECULAR_WEIGHT>
330.2458

> <EXACT_MASS>
330.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.7897781479046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4,9-trihydroxy-9-methyl-5,8,10-trioxo-5,8,9,10-tetrahydrophenanthrene-2-carboxylic acid

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
2.0611319189999997

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.33527909702024

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.313058098269274

> <JCHEM_PKA_STRONGEST_BASIC>
-3.996659013389702

> <JCHEM_POLAR_SURFACE_AREA>
149.2

> <JCHEM_REFRACTIVITY>
81.13299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4,9-trihydroxy-9-methyl-5,8,10-trioxophenanthrene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030643
     RDKit          3D
Blighinone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.4511   -1.9954    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787   -1.1700   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015   -1.4603   -1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -1.5887   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082   -2.8026   -0.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -0.6514   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -1.1242   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612   -2.4430   -0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975   -0.2833    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714   -0.7433    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586    0.0960    0.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -2.0441    0.0808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7597    1.0228    0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    1.5299    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122    2.8373    0.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.6766    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330    1.1248    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943    0.2574   -0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.7663   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -0.0627   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434    2.1245   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6887    2.9300    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    2.4915    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547    3.3412    0.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807   -1.4487    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9580   -2.9837    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4540   -2.1714   -0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -2.3781   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9942   -3.0581   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -2.2924   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801    1.6611    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022    3.4040    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942    2.4732   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    3.9649    0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  2  1  0
 16  6  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  8 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 21 33  1  0
 22 34  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      -1.191  -3.487   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.769   2.030   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.539   0.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.391   2.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.161   0.696   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.229   2.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.769  -0.637   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.851   2.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.081   0.696   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.459   0.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.851  -0.637   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.229  -0.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.391  -0.637   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.081  -1.971   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.701   0.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.459  -1.971   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.459   3.364   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.539  -1.971   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.081   3.364   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.161  -1.971   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.851  -3.305   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.471   2.030   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.471  -0.637   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.906  -2.498   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4   13   15                                                  
CONECT    6    2   10   17                                                  
CONECT    7    3   12   18                                                  
CONECT    8    4    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    6    9   12                                                  
CONECT   11    9   13   14                                                  
CONECT   12    7   10   16                                                  
CONECT   13    5   11   20                                                  
CONECT   14   11   16   21                                                  
CONECT   15    5   22   23                                                  
CONECT   16    1   12   14   24                                             
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030643
HETATM    1  C1  UNL     1      -2.451  -1.995   0.360  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.679  -1.170  -0.679  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.201  -1.460  -1.936  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.277  -1.589  -0.577  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.008  -2.803  -0.863  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.763  -0.651  -0.165  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.091  -1.124  -0.088  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.261  -2.443  -0.417  1.00  0.00           O  
HETATM    9  C6  UNL     1       3.098  -0.283   0.293  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.471  -0.743   0.380  1.00  0.00           C  
HETATM   11  O4  UNL     1       5.359   0.096   0.742  1.00  0.00           O  
HETATM   12  O5  UNL     1       4.800  -2.044   0.081  1.00  0.00           O  
HETATM   13  C8  UNL     1       2.760   1.023   0.592  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.466   1.530   0.530  1.00  0.00           C  
HETATM   15  O6  UNL     1       1.312   2.837   0.858  1.00  0.00           O  
HETATM   16  C10 UNL     1       0.472   0.677   0.148  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.933   1.125   0.052  1.00  0.00           C  
HETATM   18  C12 UNL     1      -1.894   0.257  -0.329  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.279   0.766  -0.405  1.00  0.00           C  
HETATM   20  O7  UNL     1      -4.175  -0.063  -0.766  1.00  0.00           O  
HETATM   21  C14 UNL     1      -3.643   2.124  -0.096  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.689   2.930   0.267  1.00  0.00           C  
HETATM   23  C16 UNL     1      -1.273   2.492   0.367  1.00  0.00           C  
HETATM   24  O8  UNL     1      -0.455   3.341   0.721  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.481  -1.449   1.321  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.958  -2.984   0.435  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.454  -2.171  -0.061  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.564  -2.378  -1.993  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.994  -3.058  -0.470  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.452  -2.292  -0.680  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.580   1.661   0.890  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.102   3.404   1.132  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.694   2.473  -0.164  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.874   3.965   0.517  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   18
CONECT    3   28
CONECT    4    5    5    6
CONECT    6    7    7   16
CONECT    7    8    9
CONECT    8   29
CONECT    9   10   13   13
CONECT   10   11   11   12
CONECT   12   30
CONECT   13   14   31
CONECT   14   15   16   16
CONECT   15   32
CONECT   16   17
CONECT   17   18   18   23
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22   33
CONECT   22   23   34
CONECT   23   24   24
END

HMDB0030643
     RDKit          3D
Blighinone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.4511   -1.9954    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787   -1.1700   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015   -1.4603   -1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -1.5887   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082   -2.8026   -0.8631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -0.6514   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -1.1242   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612   -2.4430   -0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975   -0.2833    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714   -0.7433    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586    0.0960    0.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -2.0441    0.0808 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7597    1.0228    0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    1.5299    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122    2.8373    0.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.6766    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330    1.1248    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943    0.2574   -0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.7663   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748   -0.0627   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434    2.1245   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6887    2.9300    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    2.4915    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547    3.3412    0.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807   -1.4487    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9580   -2.9837    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4540   -2.1714   -0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636   -2.3781   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9942   -3.0581   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -2.2924   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801    1.6611    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022    3.4040    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6942    2.4732   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    3.9649    0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  2  1  0
 16  6  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  8 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 21 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4,9-Trihydroxy-9-methyl-5,8,10-trioxo-5,8,9,10-tetrahydrophenanthrene-2-carboxylate	HMDB

Chemical Formula

C₁₆H₁₀O₈

Average Molecular Weight

330.2458

Monoisotopic Molecular Weight

330.037567296

IUPAC Name

1,4,9-trihydroxy-9-methyl-5,8,10-trioxo-5,8,9,10-tetrahydrophenanthrene-2-carboxylic acid

Traditional Name

1,4,9-trihydroxy-9-methyl-5,8,10-trioxophenanthrene-2-carboxylic acid

CAS Registry Number

20544-62-1

SMILES

CC1(O)C(=O)C2=C(O)C(=CC(O)=C2C2=C1C(=O)C=CC2=O)C(O)=O

InChI Identifier

InChI=1S/C16H10O8/c1-16(24)12-7(18)3-2-6(17)10(12)9-8(19)4-5(15(22)23)13(20)11(9)14(16)21/h2-4,19-20,24H,1H3,(H,22,23)

InChI Key

YFUQJMOETZJFHO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Dihydroxybenzoic acid
1-naphthol
Hydroxybenzoic acid
Naphthalene
Salicylic acid or derivatives
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Acyloin
Tertiary alcohol
Vinylogous acid
Ketone
Polyol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030643)
Cell membrane (HMDB: HMDB0030643)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030643)

Source

Endogenous

Endogenous (HMDB: HMDB0030643)

Plant

Plant (HMDB: HMDB0030643)

Exogenous

Food

Food (HMDB: HMDB0030643)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030643)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	448200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.02 g/L	ALOGPS
logP	1.31	ALOGPS
logP	2.06	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.31	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	149.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.13 m³·mol⁻¹	ChemAxon
Polarizability	29.79 Å³	ChemAxon
Number of Rings	3	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]+	175.4	31661259
DarkChem	[M-H]-	172.266	31661259
DeepCCS	[M+H]+	182.491	30932474
DeepCCS	[M-H]-	180.11	30932474
DeepCCS	[M-2H]-	214.425	30932474
DeepCCS	[M+Na]+	190.082	30932474
AllCCS	[M+H]+	172.5	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.3	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	171.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Blighinone	CC1(O)C(=O)C2=C(O)C(=CC(O)=C2C2=C1C(=O)C=CC2=O)C(O)=O	5014.5	Standard polar	33892256
Blighinone	CC1(O)C(=O)C2=C(O)C(=CC(O)=C2C2=C1C(=O)C=CC2=O)C(O)=O	2367.1	Standard non polar	33892256
Blighinone	CC1(O)C(=O)C2=C(O)C(=CC(O)=C2C2=C1C(=O)C=CC2=O)C(O)=O	2866.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Blighinone,1TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)C2=C(O)C(C(=O)O)=CC(O)=C2C2=C1C(=O)C=CC2=O	2964.4	Semi standard non polar	33892256
Blighinone,1TMS,isomer #2	CC1(O)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O)=CC(O)=C2C2=C1C(=O)C=CC2=O	2950.3	Semi standard non polar	33892256
Blighinone,1TMS,isomer #3	CC1(O)C(=O)C2=C(O)C(C(=O)O)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2948.2	Semi standard non polar	33892256
Blighinone,1TMS,isomer #4	CC1(O)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	2982.9	Semi standard non polar	33892256
Blighinone,2TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O)=CC(O)=C2C2=C1C(=O)C=CC2=O	2888.1	Semi standard non polar	33892256
Blighinone,2TMS,isomer #2	CC1(O[Si](C)(C)C)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	2913.2	Semi standard non polar	33892256
Blighinone,2TMS,isomer #3	CC1(O[Si](C)(C)C)C(=O)C2=C(O)C(C(=O)O)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2887.5	Semi standard non polar	33892256
Blighinone,2TMS,isomer #4	CC1(O)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	2926.4	Semi standard non polar	33892256
Blighinone,2TMS,isomer #5	CC1(O)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2894.3	Semi standard non polar	33892256
Blighinone,2TMS,isomer #6	CC1(O)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2931.0	Semi standard non polar	33892256
Blighinone,3TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	2890.3	Semi standard non polar	33892256
Blighinone,3TMS,isomer #2	CC1(O[Si](C)(C)C)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2892.5	Semi standard non polar	33892256
Blighinone,3TMS,isomer #3	CC1(O[Si](C)(C)C)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2892.8	Semi standard non polar	33892256
Blighinone,3TMS,isomer #4	CC1(O)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2894.0	Semi standard non polar	33892256
Blighinone,4TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)C2=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C2=C1C(=O)C=CC2=O	2878.0	Semi standard non polar	33892256
Blighinone,1TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O)C(C(=O)O)=CC(O)=C2C2=C1C(=O)C=CC2=O	3188.4	Semi standard non polar	33892256
Blighinone,1TBDMS,isomer #2	CC1(O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=CC(O)=C2C2=C1C(=O)C=CC2=O	3176.4	Semi standard non polar	33892256
Blighinone,1TBDMS,isomer #3	CC1(O)C(=O)C2=C(O)C(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3178.9	Semi standard non polar	33892256
Blighinone,1TBDMS,isomer #4	CC1(O)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	3253.9	Semi standard non polar	33892256
Blighinone,2TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=CC(O)=C2C2=C1C(=O)C=CC2=O	3360.9	Semi standard non polar	33892256
Blighinone,2TBDMS,isomer #2	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	3396.7	Semi standard non polar	33892256
Blighinone,2TBDMS,isomer #3	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O)C(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3351.1	Semi standard non polar	33892256
Blighinone,2TBDMS,isomer #4	CC1(O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	3401.6	Semi standard non polar	33892256
Blighinone,2TBDMS,isomer #5	CC1(O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3367.4	Semi standard non polar	33892256
Blighinone,2TBDMS,isomer #6	CC1(O)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3402.5	Semi standard non polar	33892256
Blighinone,3TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C2C2=C1C(=O)C=CC2=O	3575.8	Semi standard non polar	33892256
Blighinone,3TBDMS,isomer #2	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3570.5	Semi standard non polar	33892256
Blighinone,3TBDMS,isomer #3	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3575.6	Semi standard non polar	33892256
Blighinone,3TBDMS,isomer #4	CC1(O)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3578.5	Semi standard non polar	33892256
Blighinone,4TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C2=C1C(=O)C=CC2=O	3734.8	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 - Blighinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w29-0479000000-23446e550a177b974081	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Blighinone GC-MS (4 TMS) - 70eV, Positive	splash10-0fkd-2110092000-14fc2a865d060499381d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Blighinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Blighinone 10V, Positive-QTOF	splash10-001i-0039000000-87571fcdbbeb1f20efed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 20V, Positive-QTOF	splash10-01p9-0096000000-9140fc55a72ea4a98da7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 40V, Positive-QTOF	splash10-0a59-1190000000-491e41b1dee4b919a52e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 10V, Negative-QTOF	splash10-004r-0069000000-62953d04ff1f366c387c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 20V, Negative-QTOF	splash10-000i-0091000000-a3a08739e5d495d48033	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 40V, Negative-QTOF	splash10-0i0c-1190000000-051a4b9262ea04505f88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 10V, Positive-QTOF	splash10-03e9-0009000000-679f067f13aa55f6bf34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 20V, Positive-QTOF	splash10-03di-0049000000-d1e16f5423f1bf8b38e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 40V, Positive-QTOF	splash10-0a4m-1090000000-8719a483fa8377795e11	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 10V, Negative-QTOF	splash10-004i-0009000000-b872c02df162363ed1dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 20V, Negative-QTOF	splash10-004i-0039000000-015a2ef63607ec86611d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Blighinone 40V, Negative-QTOF	splash10-02tc-0090000000-a0a2401da54e644b6f65	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB002548

KNApSAcK ID

Not Available

Chemspider ID

35013247

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137185904

PDB ID

Not Available

ChEBI ID

175199

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1821701

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 Blighinone (HMDB0030643)

MOL for HMDB0030643 (Blighinone)

3D MOL for HMDB0030643 (Blighinone)

3D SDF for HMDB0030643 (Blighinone)

3D-SDF for HMDB0030643 (Blighinone)

PDB for HMDB0030643 (Blighinone)

3D PDB for HMDB0030643 (Blighinone)

SMILES for HMDB0030643 (Blighinone)

INCHI for HMDB0030643 (Blighinone)

Structure for HMDB0030643 (Blighinone)

3D Structure for HMDB0030643 (Blighinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra