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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:10:17 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012942

Secondary Accession Numbers

HMDB12942

Metabolite Identification

Common Name

Estrone-3,4-quinone

Description

Estrogen 2,3- and 3,4-quinones are reactive species toward nucleophiles and Michael acceptors. As such, they can bind to DNA and induce cellular damages.Tumors may arise in cells covalently damaged by the free radicals or by the quinones and stimulated to proliferate by hormone receptor-mediated. processes. This hypothesis is supported by the correlation between quinone formation, 8-hydroxylation of guanine bases of DNA and tumor incidence of 4- versus 2-hydroxylated estrogen metabolites. Moreover, estrone-3,4-quinone, but not. estrone-2,3-quinone, induced liver tumors in mice.

Structure

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

HMDB0012942
     RDKit          3D
Estrone-3,4-quinone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.6793    1.1347   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.0390    0.4300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6633    0.3399    1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.0202    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742    0.5297    0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587    0.5184    0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622    0.5781   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851    0.6581   -1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566    0.1747   -1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119   -0.4370   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335   -0.9339   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.2926   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.6540   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -0.9769    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -1.1291    1.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396    0.5659   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6820    0.6201   -1.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857    0.4918    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    0.4810    0.7109 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0453    0.4300    1.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7168    0.4443    1.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    0.8128   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    1.7200    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184    1.8272   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -0.2818    2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    1.4044    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -1.0852    1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865    0.5054    2.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978    1.5749    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    0.0843   -2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    1.7366   -2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418    0.9538   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862   -0.6448   -2.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8340   -1.3023   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2106   -1.8806    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6886   -2.2003   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -0.4995   -2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2182   -1.2726   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884   -2.7457   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851    0.3739    2.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073    0.3952    2.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 11  2  1  0
 14  2  1  0
 10  5  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 20 40  1  0
 21 41  1  0
M  END

  Mrv1652303262014172D          

 21 24  0  0  1  0            999 V2000
   16.8395  -14.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3083  -13.9323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8958  -14.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0708  -14.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6583  -13.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0708  -13.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6583  -12.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8333  -12.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4208  -13.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8333  -13.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4208  -14.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5958  -14.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1833  -13.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3582  -13.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5958  -13.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1833  -12.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8958  -13.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4479  -12.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2015  -12.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1153  -13.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7284  -14.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012942

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12CCC3C(CCC4=C3C=CC(=O)C4=O)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14H,2-3,5,7-9H2,1H3/t11?,12?,14?,18-/m0/s1

> <INCHI_KEY>
REMSDZFYMQQJFD-PEDDLLMLSA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.3496

> <EXACT_MASS>
284.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.993852160789647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-diene-5,6,14-trione

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
3.5799097686666674

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.957534131026907

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4612710862820215

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
80.77919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-diene-5,6,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012942
     RDKit          3D
Estrone-3,4-quinone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.6793    1.1347   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.0390    0.4300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6633    0.3399    1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.0202    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742    0.5297    0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587    0.5184    0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622    0.5781   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851    0.6581   -1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566    0.1747   -1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119   -0.4370   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335   -0.9339   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.2926   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.6540   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -0.9769    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -1.1291    1.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396    0.5659   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6820    0.6201   -1.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857    0.4918    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    0.4810    0.7109 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0453    0.4300    1.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7168    0.4443    1.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    0.8128   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    1.7200    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184    1.8272   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -0.2818    2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    1.4044    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -1.0852    1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865    0.5054    2.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978    1.5749    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    0.0843   -2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    1.7366   -2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418    0.9538   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862   -0.6448   -2.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8340   -1.3023   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2106   -1.8806    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6886   -2.2003   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -0.4995   -2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2182   -1.2726   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884   -2.7457   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851    0.3739    2.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073    0.3952    2.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 11  2  1  0
 14  2  1  0
 10  5  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 20 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      31.434 -27.185   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.442 -26.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.672 -27.341   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.132 -27.341   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.362 -26.007   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.132 -24.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.362 -23.339   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.822 -23.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.052 -24.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.822 -26.007   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.052 -27.341   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.512 -27.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.742 -26.007   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.202 -26.007   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.512 -24.673   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      22.742 -23.339   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      29.672 -24.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.703 -23.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.109 -24.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.949 -25.687   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      33.093 -26.717   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    5    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15    9   13   16                                                  
CONECT   16   15                                                            
CONECT   17    2    6   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    2   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0012942
HETATM    1  C1  UNL     1      -2.679   1.135  -0.384  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.202  -0.039   0.430  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.663   0.340   1.762  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.184   0.020   1.841  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.474   0.530   0.607  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.959   0.518   0.645  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.562   0.578  -0.529  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.885   0.658  -1.830  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.457   0.175  -1.836  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.112  -0.437  -0.532  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.233  -0.934  -0.320  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.067  -1.293  -1.520  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.395  -1.654  -0.829  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.352  -0.977   0.484  1.00  0.00           C  
HETATM   15  O1  UNL     1      -4.080  -1.129   1.422  1.00  0.00           O  
HETATM   16  C15 UNL     1       4.040   0.566  -0.531  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.682   0.620  -1.613  1.00  0.00           O  
HETATM   18  C16 UNL     1       4.786   0.492   0.705  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.047   0.481   0.711  1.00  0.00           O  
HETATM   20  C17 UNL     1       4.045   0.430   1.941  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.717   0.444   1.880  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.338   0.813  -1.206  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.349   1.720   0.313  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.918   1.827  -0.721  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.168  -0.282   2.532  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.871   1.404   2.004  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.079  -1.085   1.866  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.186   0.505   2.768  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.198   1.575   0.353  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.514   0.084  -2.567  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.934   1.737  -2.164  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.242   0.954  -2.190  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.386  -0.645  -2.611  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.834  -1.302  -0.399  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.211  -1.881   0.305  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.689  -2.200  -2.027  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.183  -0.500  -2.253  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.218  -1.273  -1.469  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.488  -2.746  -0.763  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.585   0.374   2.881  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.207   0.395   2.847  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   11   14
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   10   29
CONECT    6    7    7   21
CONECT    7    8   16
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   34
CONECT   11   12   35
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   15
CONECT   16   17   17   18
CONECT   18   19   19   20
CONECT   20   21   21   40
CONECT   21   41
END

HMDB0012942
     RDKit          3D
Estrone-3,4-quinone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.6793    1.1347   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -0.0390    0.4300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6633    0.3399    1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.0202    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742    0.5297    0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587    0.5184    0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622    0.5781   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851    0.6581   -1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566    0.1747   -1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119   -0.4370   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335   -0.9339   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -1.2926   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.6540   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522   -0.9769    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -1.1291    1.4223 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396    0.5659   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6820    0.6201   -1.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857    0.4918    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    0.4810    0.7109 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0453    0.4300    1.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7168    0.4443    1.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    0.8128   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    1.7200    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184    1.8272   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -0.2818    2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    1.4044    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -1.0852    1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865    0.5054    2.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978    1.5749    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    0.0843   -2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    1.7366   -2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418    0.9538   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862   -0.6448   -2.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8340   -1.3023   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2106   -1.8806    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6886   -2.2003   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -0.4995   -2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2182   -1.2726   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884   -2.7457   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851    0.3739    2.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073    0.3952    2.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 11  2  1  0
 14  2  1  0
 10  5  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 20 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Catecholestrogen quinone	HMDB

Chemical Formula

C₁₈H₂₀O₃

Average Molecular Weight

284.3496

Monoisotopic Molecular Weight

284.141244506

IUPAC Name

(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-diene-5,6,14-trione

Traditional Name

(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-diene-5,6,14-trione

CAS Registry Number

633-34-1

SMILES

C[C@]12CCC3C(CCC4=C3C=CC(=O)C4=O)C1CCC2=O

InChI Identifier

InChI=1S/C18H20O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14H,2-3,5,7-9H2,1H3/t11?,12?,14?,18-/m0/s1

InChI Key

REMSDZFYMQQJFD-PEDDLLMLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

4-oxosteroid
Oxosteroid
17-oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012942)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0012942)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012942)

Source

Endogenous

Endogenous (HMDB: HMDB0012942)

Animal

Animal (HMDB: HMDB0012942)

Exogenous

Food

Food (HMDB: HMDB0012942)

Exogenous (HMDB: HMDB0012942)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012942)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012942)

Lipid metabolism pathway (HMDB: HMDB0012942)

Cellular process

Cell signaling (HMDB: HMDB0012942)

Biochemical process

Lipid transport (HMDB: HMDB0012942)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012942)

Molecular messenger

Signaling molecule (HMDB: HMDB0012942)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012942)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.62	ALOGPS
logP	3.58	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.78 m³·mol⁻¹	ChemAxon
Polarizability	30.99 Å³	ChemAxon
Number of Rings	4	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]+	165.77	31661259
DarkChem	[M-H]-	163.904	31661259
DeepCCS	[M-2H]-	200.912	30932474
DeepCCS	[M+Na]+	176.285	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.7	32859911
AllCCS	[M+NH4]+	172.1	32859911
AllCCS	[M+Na]+	173.0	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	174.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estrone-3,4-quinone	C[C@]12CCC3C(CCC4=C3C=CC(=O)C4=O)C1CCC2=O	3303.7	Standard polar	33892256
Estrone-3,4-quinone	C[C@]12CCC3C(CCC4=C3C=CC(=O)C4=O)C1CCC2=O	2450.8	Standard non polar	33892256
Estrone-3,4-quinone	C[C@]12CCC3C(CCC4=C3C=CC(=O)C4=O)C1CCC2=O	2766.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estrone-3,4-quinone,1TMS,isomer #1	C[C@]12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)C(=O)C(=O)C=C4	2821.6	Semi standard non polar	33892256
Estrone-3,4-quinone,1TMS,isomer #1	C[C@]12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)C(=O)C(=O)C=C4	2515.3	Standard non polar	33892256
Estrone-3,4-quinone,1TMS,isomer #1	C[C@]12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)C(=O)C(=O)C=C4	3223.1	Standard polar	33892256
Estrone-3,4-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(=O)C4=O)C3CC[C@]12C	3051.8	Semi standard non polar	33892256
Estrone-3,4-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(=O)C4=O)C3CC[C@]12C	2726.5	Standard non polar	33892256
Estrone-3,4-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(=O)C4=O)C3CC[C@]12C	3412.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone-3,4-quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0490000000-9be895d344e0d9e1cf83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone-3,4-quinone 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 - Estrone-3,4-quinone 10V, Positive-QTOF	splash10-000i-0090000000-4b4ab19eb7e66c4262ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 20V, Positive-QTOF	splash10-0pvr-0290000000-d46c881d8d44c24911aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 40V, Positive-QTOF	splash10-0v00-5970000000-87556cb0066f940f1546	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 10V, Negative-QTOF	splash10-001i-0090000000-26186862995a22d55c38	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 20V, Negative-QTOF	splash10-001i-0090000000-a5566cade01509136d1c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 40V, Negative-QTOF	splash10-0lfr-1090000000-a4ecefb9516746fd0afd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 10V, Positive-QTOF	splash10-000i-0090000000-15149c6d9df42998fed4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 20V, Positive-QTOF	splash10-014i-0290000000-202177f97c74d6600c48	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 40V, Positive-QTOF	splash10-004i-3950000000-e3da4f1e4ec392724730	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 10V, Negative-QTOF	splash10-001i-0090000000-78a425e25a58a7330ede	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 20V, Negative-QTOF	splash10-001i-0090000000-66be572965738623efe2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-3,4-quinone 40V, Negative-QTOF	splash10-0059-0290000000-a051872aa445f8cb783e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB029220

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481560

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE5251

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Glutathione S-transferase theta-2

General function:: Posttranslational modification, protein turnover, chaperones
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a sulfatase activity.
Gene Name:: GSTT2
Uniprot ID:: P0CG29
Molecular weight:: Not Available

Showing metabocard for Estrone-3,4-quinone (HMDB0012942)

MOL for HMDB0012942 (Estrone-3,4-quinone)

3D MOL for HMDB0012942 (Estrone-3,4-quinone)

3D SDF for HMDB0012942 (Estrone-3,4-quinone)

3D-SDF for HMDB0012942 (Estrone-3,4-quinone)

PDB for HMDB0012942 (Estrone-3,4-quinone)

3D PDB for HMDB0012942 (Estrone-3,4-quinone)

SMILES for HMDB0012942 (Estrone-3,4-quinone)

INCHI for HMDB0012942 (Estrone-3,4-quinone)

Structure for HMDB0012942 (Estrone-3,4-quinone)

3D Structure for HMDB0012942 (Estrone-3,4-quinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes