Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:10:16 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012941

Secondary Accession Numbers

HMDB12941

Metabolite Identification

Common Name

Estrone-2,3-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

HMDB0012941
     RDKit          3D
Estrone-2,3-quinone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.4573    0.5057   -1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    0.6823   -0.0061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4495    1.9220    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7826   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.6338    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    0.5036    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8343    1.5683    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    1.5343   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0162    2.5387    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    0.2679   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985    0.1480   -0.7037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553   -0.8873   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6640   -0.7630   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8281   -2.0010   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -1.8078    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.6347    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752   -0.4892    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -1.5909    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739   -0.8941    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051    0.5560    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1860    1.4722    1.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    1.5084   -1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.2696   -2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -0.1906   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    2.8451   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    1.9685    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    1.5342   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095    2.7346   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223    0.7564    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    2.5297    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3842   -1.8417   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -2.1680   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -2.8994   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -1.6008    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -2.7471    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -0.6887   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -0.2434    1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -2.3370    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730   -2.1015   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4798   -1.1842   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1461   -1.1915    1.7915 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  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 16  5  1  0
 13  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
  7 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
M  END


  Mrv1652303262014172D          

 21 24  0  0  1  0            999 V2000
   14.9409  -11.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4096  -11.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9971  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1721  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7596  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1721  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7596   -9.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9346   -9.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5221  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6971  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4596  -11.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6971  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846  -12.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5221  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9346  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9971  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5492   -9.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3029  -10.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2167  -10.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8298  -11.4166    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 16  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 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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>
HMDB0012941

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14H,2-7H2,1H3/t11?,12?,14?,18-/m0/s1

> <INCHI_KEY>
WFPLOQDPWXNOST-PEDDLLMLSA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.3496

> <EXACT_MASS>
284.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.260076818988736

> <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-2,6-diene-4,5,14-trione

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
3.4277205510000006

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.392798621017317

> <JCHEM_PKA_STRONGEST_BASIC>
-7.459250302087497

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
80.70409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012941
     RDKit          3D
Estrone-2,3-quinone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.4573    0.5057   -1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    0.6823   -0.0061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4495    1.9220    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7826   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.6338    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    0.5036    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8343    1.5683    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    1.5343   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0162    2.5387    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    0.2679   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985    0.1480   -0.7037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553   -0.8873   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6640   -0.7630   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8281   -2.0010   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -1.8078    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.6347    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752   -0.4892    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -1.5909    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739   -0.8941    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051    0.5560    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1860    1.4722    1.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    1.5084   -1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.2696   -2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -0.1906   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    2.8451   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    1.9685    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    1.5342   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095    2.7346   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223    0.7564    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    2.5297    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3842   -1.8417   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -2.1680   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -2.8994   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -1.6008    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -2.7471    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -0.6887   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -0.2434    1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -2.3370    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730   -2.1015   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4798   -1.1842   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1461   -1.1915    1.7915 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  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 16  5  1  0
 13  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
  7 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 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      27.890 -21.779   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.898 -20.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.128 -21.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.588 -21.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.818 -20.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.588 -19.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.818 -17.933   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.278 -17.933   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.508 -19.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.968 -19.267   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.198 -20.601   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.658 -20.601   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.968 -21.934   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      19.198 -23.268   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.508 -21.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.278 -20.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.128 -19.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.159 -18.123   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.565 -18.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.405 -20.281   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      29.549 -21.311   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   16                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16    5    9   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    HMDB0012941
HETATM    1  C1  UNL     1      -2.457   0.506  -1.478  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.199   0.682  -0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.449   1.922   0.316  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.050   1.783  -0.295  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.635   0.634   0.391  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.059   0.504   0.105  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.834   1.568   0.203  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.266   1.534  -0.063  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.016   2.539   0.025  1.00  0.00           O  
HETATM   10  C9  UNL     1       4.863   0.268  -0.454  1.00  0.00           C  
HETATM   11  O2  UNL     1       6.099   0.148  -0.704  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.955  -0.887  -0.548  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.664  -0.763  -0.287  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.828  -2.001  -0.412  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.647  -1.808   0.540  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.144  -0.635   0.002  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.475  -0.489   0.613  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.441  -1.591   0.481  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.774  -0.894   0.793  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.505   0.556   0.680  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.186   1.472   1.058  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.831   1.508  -1.842  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.590   0.270  -2.083  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.301  -0.191  -1.675  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.938   2.845  -0.073  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.295   1.969   1.409  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.159   1.534  -1.371  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.510   2.735  -0.188  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.422   0.756   1.492  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.420   2.530   0.492  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.384  -1.842  -0.838  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.511  -2.168  -1.445  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.364  -2.899  -0.058  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.065  -1.601   1.527  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.061  -2.747   0.495  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.098  -0.689  -1.085  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.349  -0.243   1.691  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.262  -2.337   1.289  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.473  -2.102  -0.486  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.480  -1.184  -0.002  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.146  -1.192   1.791  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   16   29
CONECT    6    7    7   13
CONECT    7    8   30
CONECT    8    9    9   10
CONECT   10   11   11   12
CONECT   12   13   13   31
CONECT   13   14
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   36
CONECT   17   18   37
CONECT   18   19   38   39
CONECT   19   20   40   41
CONECT   20   21   21
END

HMDB0012941
     RDKit          3D
Estrone-2,3-quinone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.4573    0.5057   -1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    0.6823   -0.0061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4495    1.9220    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7826   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351    0.6338    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    0.5036    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8343    1.5683    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    1.5343   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0162    2.5387    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    0.2679   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985    0.1480   -0.7037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553   -0.8873   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6640   -0.7630   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8281   -2.0010   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -1.8078    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.6347    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752   -0.4892    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -1.5909    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739   -0.8941    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051    0.5560    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1860    1.4722    1.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    1.5084   -1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.2696   -2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -0.1906   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    2.8451   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    1.9685    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    1.5342   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095    2.7346   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223    0.7564    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    2.5297    0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3842   -1.8417   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -2.1680   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -2.8994   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -1.6008    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -2.7471    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -0.6887   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -0.2434    1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -2.3370    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730   -2.1015   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4798   -1.1842   -0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1461   -1.1915    1.7915 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  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 16  5  1  0
 13  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
  7 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 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-2,6-diene-4,5,14-trione

Traditional Name

(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione

CAS Registry Number

40551-33-5

SMILES

C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O

InChI Identifier

InChI=1S/C18H20O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14H,2-7H2,1H3/t11?,12?,14?,18-/m0/s1

InChI Key

WFPLOQDPWXNOST-PEDDLLMLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
2-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: HMDB0012941)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0012941)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012941)

Source

Endogenous

Endogenous (HMDB: HMDB0012941)

Animal

Animal (HMDB: HMDB0012941)

Exogenous

Food

Food (HMDB: HMDB0012941)

Exogenous (HMDB: HMDB0012941)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012941)

Molecular messenger

Signaling molecule (HMDB: HMDB0012941)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012941)

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	0.041 g/L	ALOGPS
logP	2.62	ALOGPS
logP	3.43	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.39	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	80.7 m³·mol⁻¹	ChemAxon
Polarizability	31.26 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]+	167.329	31661259
DarkChem	[M-H]-	162.685	31661259
DeepCCS	[M-2H]-	203.829	30932474
DeepCCS	[M+Na]+	179.213	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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.46 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4117 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2297.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	487.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	235.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	594.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	689.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1396.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1422.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	507.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estrone-2,3-quinone	C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O	3380.8	Standard polar	33892256
Estrone-2,3-quinone	C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O	2443.0	Standard non polar	33892256
Estrone-2,3-quinone	C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O	2881.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estrone-2,3-quinone,1TMS,isomer #1	C[C@]12CCC3C4=CC(=O)C(=O)C=C4CCC3C1CC=C2O[Si](C)(C)C	2797.2	Semi standard non polar	33892256
Estrone-2,3-quinone,1TMS,isomer #1	C[C@]12CCC3C4=CC(=O)C(=O)C=C4CCC3C1CC=C2O[Si](C)(C)C	2521.1	Standard non polar	33892256
Estrone-2,3-quinone,1TMS,isomer #1	C[C@]12CCC3C4=CC(=O)C(=O)C=C4CCC3C1CC=C2O[Si](C)(C)C	3303.1	Standard polar	33892256
Estrone-2,3-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=CC(=O)C(=O)C=C4C3CC[C@]12C	3024.8	Semi standard non polar	33892256
Estrone-2,3-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=CC(=O)C(=O)C=C4C3CC[C@]12C	2722.4	Standard non polar	33892256
Estrone-2,3-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=CC(=O)C(=O)C=C4C3CC[C@]12C	3501.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone-2,3-quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0590000000-8c8c122e6d9b125e2f7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone-2,3-quinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone-2,3-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-2,3-quinone 10V, Positive-QTOF	splash10-000i-0090000000-3640f8d8cf7d72931785	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Positive-QTOF	splash10-05n0-0290000000-ac6ebae2649658cc06a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Positive-QTOF	splash10-0udi-5590000000-bf0202392e0921e34265	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Negative-QTOF	splash10-001i-0090000000-b52ab2d316b4a1905ea3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Negative-QTOF	splash10-001i-0090000000-875af10e53aa400e62ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Negative-QTOF	splash10-0lg0-0090000000-11e6d40e9af6a5876328	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Negative-QTOF	splash10-001i-0090000000-78a425e25a58a7330ede	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Negative-QTOF	splash10-001i-0090000000-1cce43a24f2838cc9557	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Negative-QTOF	splash10-0fai-0190000000-a9d81c8838a462df3bcc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 10V, Positive-QTOF	splash10-000i-0090000000-8cb5c211dee4a6b288ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 20V, Positive-QTOF	splash10-02t9-1590000000-ed6a18c605a9e5c85c55	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone-2,3-quinone 40V, Positive-QTOF	splash10-004r-3920000000-f3aa5a90c960a060e7b0	2021-09-24	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

FDB029219

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

53481559

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE5252

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-2,3-quinone (HMDB0012941)

MOL for HMDB0012941 (Estrone-2,3-quinone)

3D MOL for HMDB0012941 (Estrone-2,3-quinone)

3D SDF for HMDB0012941 (Estrone-2,3-quinone)

3D-SDF for HMDB0012941 (Estrone-2,3-quinone)

PDB for HMDB0012941 (Estrone-2,3-quinone)

3D PDB for HMDB0012941 (Estrone-2,3-quinone)

SMILES for HMDB0012941 (Estrone-2,3-quinone)

INCHI for HMDB0012941 (Estrone-2,3-quinone)

Structure for HMDB0012941 (Estrone-2,3-quinone)

3D Structure for HMDB0012941 (Estrone-2,3-quinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes