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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:47 UTC

Update Date

2022-03-07 02:52:40 UTC

HMDB ID

HMDB0030744

Secondary Accession Numbers

HMDB30744

Metabolite Identification

Common Name

Hemigossypolone

Description

Hemigossypolone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Hemigossypolone.

Structure

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

HMDB0030744
     RDKit          3D
Hemigossypolone
 34 35  0  0  0  0  0  0  0  0999 V2000
    2.9554   -1.8922   -2.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246   -0.8785   -1.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.0783   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0794   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432    1.9679    0.3844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    1.0206    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613    1.9399    1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513    2.9730    1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    3.7986    2.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    1.8234    1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    2.7390    2.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778    0.8521    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    0.7438    1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9241   -0.1100    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811   -1.2471   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251   -1.2326   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0412   -1.4310    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961    0.0021   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9911   -0.9604   -1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346   -1.8860   -1.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -1.8011   -2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6288   -1.6671   -3.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -2.9397   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.1295   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5852    3.1879    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294    2.7847    3.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1159    1.4092    2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -2.2329   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -0.3750   -2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3086   -1.0608   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -2.1555   -2.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -0.8475    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -2.5133    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -1.2986    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 19  2  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 11 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv0541 05061305282D          

 20 21  0  0  0  0            999 V2000
    3.5724   -2.8875    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  5  2  0  0  0  0
 17  9  2  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030744

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C2C(=O)C(C)=CC(=O)C2=C(C=O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-6(2)10-12-11(8(5-16)14(19)15(10)20)9(17)4-7(3)13(12)18/h4-6,19-20H,1-3H3

> <INCHI_KEY>
CERPPXZGSNEVMI-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.45551287735214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxy-6-methyl-5,8-dioxo-4-(propan-2-yl)-5,8-dihydronaphthalene-1-carbaldehyde

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.8902492920000005

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.460350322112118

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.6906248029508415

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9885301125011905

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
75.2769

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-4-isopropyl-6-methyl-5,8-dioxonaphthalene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030744
     RDKit          3D
Hemigossypolone
 34 35  0  0  0  0  0  0  0  0999 V2000
    2.9554   -1.8922   -2.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246   -0.8785   -1.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.0783   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0794   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432    1.9679    0.3844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    1.0206    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613    1.9399    1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513    2.9730    1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    3.7986    2.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    1.8234    1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    2.7390    2.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778    0.8521    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    0.7438    1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9241   -0.1100    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811   -1.2471   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251   -1.2326   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0412   -1.4310    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961    0.0021   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9911   -0.9604   -1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346   -1.8860   -1.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -1.8011   -2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6288   -1.6671   -3.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -2.9397   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.1295   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5852    3.1879    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294    2.7847    3.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1159    1.4092    2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -2.2329   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -0.3750   -2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3086   -1.0608   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -2.1555   -2.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -0.8475    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -2.5133    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -1.2986    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 19  2  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 11 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 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       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    7    9                                                       
CONECT    5    8   16                                                       
CONECT    6    1    2   10                                                  
CONECT    7    3    4   13                                                  
CONECT    8    5   11   14                                                  
CONECT    9    4   11   17                                                  
CONECT   10    6   12   15                                                  
CONECT   11    8    9   12                                                  
CONECT   12   10   11   13                                                  
CONECT   13    7   12   18                                                  
CONECT   14    8   15   19                                                  
CONECT   15   10   14   20                                                  
CONECT   16    5                                                            
CONECT   17    9                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030744
HETATM    1  C1  UNL     1       2.955  -1.892  -2.378  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.425  -0.878  -1.440  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.167   0.078  -0.954  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.638   1.079  -0.032  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.443   1.968   0.384  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.240   1.021   0.370  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.761   1.940   1.272  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.551   2.973   1.840  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.006   3.799   2.685  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.583   1.823   1.661  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.064   2.739   2.555  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.378   0.852   1.176  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.722   0.744   1.562  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.924  -0.110   0.253  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.781  -1.247  -0.089  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.125  -1.233  -1.550  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.041  -1.431   0.702  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.396   0.002  -0.136  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.991  -0.960  -1.048  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.335  -1.886  -1.526  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.075  -1.801  -2.366  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.629  -1.667  -3.399  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.748  -2.940  -2.062  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.211   0.130  -1.240  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.585   3.188   1.681  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.929   2.785   3.024  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.116   1.409   2.189  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.178  -2.233  -0.009  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.743  -0.375  -2.124  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.309  -1.061  -1.579  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.075  -2.155  -2.101  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.908  -0.848   0.364  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.352  -2.513   0.519  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.928  -1.299   1.797  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   19
CONECT    3    4   24
CONECT    4    5    5    6
CONECT    6    7    7   18
CONECT    7    8   10
CONECT    8    9    9   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   13   14
CONECT   13   27
CONECT   14   15   18   18
CONECT   15   16   17   28
CONECT   16   29   30   31
CONECT   17   32   33   34
CONECT   18   19
CONECT   19   20   20
END

HMDB0030744
     RDKit          3D
Hemigossypolone
 34 35  0  0  0  0  0  0  0  0999 V2000
    2.9554   -1.8922   -2.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246   -0.8785   -1.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    0.0783   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0794   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432    1.9679    0.3844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    1.0206    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613    1.9399    1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513    2.9730    1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    3.7986    2.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    1.8234    1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    2.7390    2.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778    0.8521    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    0.7438    1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9241   -0.1100    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811   -1.2471   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251   -1.2326   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0412   -1.4310    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961    0.0021   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9911   -0.9604   -1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346   -1.8860   -1.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754   -1.8011   -2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6288   -1.6671   -3.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -2.9397   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.1295   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5852    3.1879    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294    2.7847    3.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1159    1.4092    2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -2.2329   -0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -0.3750   -2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3086   -1.0608   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -2.1555   -2.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -0.8475    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -2.5133    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -1.2986    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 19  2  1  0
 18  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 11 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,8-Dihydro-2,3-dihydroxy-6-methyl-4-(1-methylethyl)-5,8-dioxo-1-naphthalenecarboxaldehyde, 9ci	HMDB
5-Formyl-6,7-dihydroxy-8-isopropyl-2-methyl-1,4-naphthoquinone	HMDB
Para-hemigossypolone	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

2,3-dihydroxy-6-methyl-5,8-dioxo-4-(propan-2-yl)-5,8-dihydronaphthalene-1-carbaldehyde

Traditional Name

2,3-dihydroxy-4-isopropyl-6-methyl-5,8-dioxonaphthalene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2C(=O)C(C)=CC(=O)C2=C(C=O)C(O)=C1O

InChI Identifier

InChI=1S/C15H14O5/c1-6(2)10-12-11(8(5-16)14(19)15(10)20)9(17)4-7(3)13(12)18/h4-6,19-20H,1-3H3

InChI Key

CERPPXZGSNEVMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cadinane sesquiterpenoid
Sesquiterpenoid
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
Aryl-aldehyde
Benzenoid
Vinylogous acid
Ketone
Organic oxide
Organic oxygen compound
Organooxygen compound
Aldehyde
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030744)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030744)

Source

Endogenous

Endogenous (HMDB: HMDB0030744)

Animal

Animal (HMDB: HMDB0030744)

Exogenous

Food

Food (HMDB: HMDB0030744)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0030744)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0030744)

Cellular process

Cell signaling (HMDB: HMDB0030744)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0030744)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0030744)

Nutrient

Nutrient (HMDB: HMDB0030744)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	166.5 - 169 °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	0.25 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.89	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.69	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.28 m³·mol⁻¹	ChemAxon
Polarizability	27.46 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.531	31661259
DarkChem	[M-H]-	161.935	31661259
DeepCCS	[M+H]+	165.02	30932474
DeepCCS	[M-H]-	162.662	30932474
DeepCCS	[M-2H]-	196.06	30932474
DeepCCS	[M+Na]+	171.287	30932474
AllCCS	[M+H]+	160.4	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.6	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	163.7	32859911
AllCCS	[M+HCOO]-	163.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hemigossypolone	CC(C)C1=C2C(=O)C(C)=CC(=O)C2=C(C=O)C(O)=C1O	3295.2	Standard polar	33892256
Hemigossypolone	CC(C)C1=C2C(=O)C(C)=CC(=O)C2=C(C=O)C(O)=C1O	2072.6	Standard non polar	33892256
Hemigossypolone	CC(C)C1=C2C(=O)C(C)=CC(=O)C2=C(C=O)C(O)=C1O	2262.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hemigossypolone,1TMS,isomer #1	CC1=CC(=O)C2=C(C=O)C(O[Si](C)(C)C)=C(O)C(C(C)C)=C2C1=O	2429.9	Semi standard non polar	33892256
Hemigossypolone,1TMS,isomer #2	CC1=CC(=O)C2=C(C=O)C(O)=C(O[Si](C)(C)C)C(C(C)C)=C2C1=O	2424.3	Semi standard non polar	33892256
Hemigossypolone,2TMS,isomer #1	CC1=CC(=O)C2=C(C=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C(C)C)=C2C1=O	2427.6	Semi standard non polar	33892256
Hemigossypolone,1TBDMS,isomer #1	CC1=CC(=O)C2=C(C=O)C(O[Si](C)(C)C(C)(C)C)=C(O)C(C(C)C)=C2C1=O	2657.5	Semi standard non polar	33892256
Hemigossypolone,1TBDMS,isomer #2	CC1=CC(=O)C2=C(C=O)C(O)=C(O[Si](C)(C)C(C)(C)C)C(C(C)C)=C2C1=O	2645.0	Semi standard non polar	33892256
Hemigossypolone,2TBDMS,isomer #1	CC1=CC(=O)C2=C(C=O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(C)C)=C2C1=O	2859.3	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 - Hemigossypolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5d-0190000000-fbb4f310a994d270a323	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hemigossypolone GC-MS (2 TMS) - 70eV, Positive	splash10-0ufv-1149500000-31b18ddd5f8a193d343a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hemigossypolone 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 - Hemigossypolone 10V, Positive-QTOF	splash10-004i-0090000000-0654ec8a200e566ee92c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 20V, Positive-QTOF	splash10-0aor-2190000000-749885b448ffe3941a14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 40V, Positive-QTOF	splash10-056r-5690000000-d8c99642cc79eb0eb3cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 10V, Negative-QTOF	splash10-00di-0090000000-cdd6f84bcd3e959ee1d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 20V, Negative-QTOF	splash10-00di-0090000000-71ab3299150161384027	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 40V, Negative-QTOF	splash10-0bti-5590000000-610ddf0acc710036c4c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 10V, Negative-QTOF	splash10-00di-0090000000-7dbb1e549f6404042b70	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 20V, Negative-QTOF	splash10-00di-0090000000-0c923b81e97e88460ab5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 40V, Negative-QTOF	splash10-0329-0980000000-fe47c0113687f3873f99	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 10V, Positive-QTOF	splash10-004i-0090000000-369e429e4458b56edc5e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 20V, Positive-QTOF	splash10-004i-0090000000-b257cb2de7c5b0c3c196	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hemigossypolone 40V, Positive-QTOF	splash10-014i-1190000000-66af933ac9aa09cd8be0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002672

KNApSAcK ID

C00057287

Chemspider ID

158510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182249

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Hemigossypolone (HMDB0030744)

MOL for HMDB0030744 (Hemigossypolone)

3D MOL for HMDB0030744 (Hemigossypolone)

3D SDF for HMDB0030744 (Hemigossypolone)

3D-SDF for HMDB0030744 (Hemigossypolone)

PDB for HMDB0030744 (Hemigossypolone)

3D PDB for HMDB0030744 (Hemigossypolone)

SMILES for HMDB0030744 (Hemigossypolone)

INCHI for HMDB0030744 (Hemigossypolone)

Structure for HMDB0030744 (Hemigossypolone)

3D Structure for HMDB0030744 (Hemigossypolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra