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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:01 UTC

HMDB ID

HMDB0000372

Secondary Accession Numbers

HMDB00372

Metabolite Identification

Common Name

16-Oxoestrone

Description

Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol.

Structure

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

HMDB0000372
     RDKit          3D
16-Oxoestrone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.7943   -0.7892    1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4605   -0.4123   -0.3709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6954   -1.4462   -1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1973   -1.3133   -0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -0.5700    0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469   -0.6104    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385   -1.8370    0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -1.9560    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -0.8544    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -0.9713    0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8378    0.3813    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.4908    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    1.8468    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5925    1.6649   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778    0.8390    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892    0.8915   -0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    1.8604    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478    1.3676   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    2.0170   -0.6573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7206    0.0072   -1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484   -0.6250   -1.8506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164   -0.1404    1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -0.7373    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.8753    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -2.4488   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071   -1.3733   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -2.3352   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -0.8481   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412   -1.1564    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -2.7642    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -2.9166    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -0.1712    0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5045    1.2271    0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809    2.3966   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    2.3959    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397    2.6276   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    1.0913   -1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4518    1.2712    1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624    1.1085   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    1.7563    1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    2.9110   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  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
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 02231218292D          

 21 24  0  0  1  0            999 V2000
    8.5913   -4.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5422   -8.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2689   -7.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2036   -7.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9302   -6.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2529   -5.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9142   -5.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1231   -8.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5775   -6.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7845   -7.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3653   -7.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6880   -6.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3493   -6.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1071   -6.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7685   -6.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9811   -5.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4215   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6720   -5.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7040   -8.4341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8004   -5.6397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5829   -4.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  1  0  0  0
  2 10  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3 11  1  0  0  0  0
 14  4  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
 13  6  1  0  0  0  0
  7 18  1  0  0  0  0
  8 11  2  0  0  0  0
  8 10  1  0  0  0  0
 15  9  1  0  0  0  0
  9 16  1  0  0  0  0
 10 12  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 16 20  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000372

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1

> <INCHI_KEY>
ANPHVANSJXDRTP-VLVBFLKRSA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.3496

> <EXACT_MASS>
284.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.48568044975113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
4.1536800366666675

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.122055044057536

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.326896663856502

> <JCHEM_PKA_STRONGEST_BASIC>
-5.448305705184045

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
79.8274

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000372
     RDKit          3D
16-Oxoestrone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.7943   -0.7892    1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4605   -0.4123   -0.3709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6954   -1.4462   -1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1973   -1.3133   -0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -0.5700    0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469   -0.6104    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385   -1.8370    0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -1.9560    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -0.8544    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -0.9713    0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8378    0.3813    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.4908    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    1.8468    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5925    1.6649   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778    0.8390    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892    0.8915   -0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    1.8604    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478    1.3676   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    2.0170   -0.6573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7206    0.0072   -1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484   -0.6250   -1.8506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164   -0.1404    1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -0.7373    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.8753    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -2.4488   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071   -1.3733   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -2.3352   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -0.8481   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412   -1.1564    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -2.7642    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -2.9166    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -0.1712    0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5045    1.2271    0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809    2.3966   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    2.3959    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397    2.6276   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    1.0913   -1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4518    1.2712    1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624    1.1085   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    1.7563    1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    2.9110   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  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
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      16.037  -8.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.079 -15.120   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.835 -13.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.313 -14.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.070 -12.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.539 -10.532   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.773  -9.611   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.430 -15.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.878 -12.051   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.664 -14.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.015 -14.823   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.484 -12.982   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.719 -12.061   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.133 -12.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.368 -11.749   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.631 -10.708   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.587  -9.576   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.188 -10.220   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.781 -15.744   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      20.161 -10.527   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      17.888  -8.066   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   10    4                                                       
CONECT    3    5   11                                                       
CONECT    4    2   14                                                       
CONECT    5    3   12                                                       
CONECT    6    7   13                                                       
CONECT    7    6   18                                                       
CONECT    8   11   10                                                       
CONECT    9   15   16                                                       
CONECT   10    2    8   12                                                  
CONECT   11    3    8   19                                                  
CONECT   12    5   10   13                                                  
CONECT   13    6   12   14                                                  
CONECT   14    4   13   15                                                  
CONECT   15    9   14   18                                                  
CONECT   16    9   20   17                                                  
CONECT   17   16   18   21                                                  
CONECT   18    1    7   15   17                                             
CONECT   19   11                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0000372
HETATM    1  C1  UNL     1      -2.794  -0.789   1.037  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.460  -0.412  -0.371  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.695  -1.446  -1.120  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.197  -1.313  -0.954  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.171  -0.570   0.309  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.647  -0.610   0.451  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.238  -1.837   0.666  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.626  -1.956   0.810  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.432  -0.854   0.740  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.813  -0.971   0.884  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.838   0.381   0.524  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.470   0.491   0.383  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.912   1.847   0.154  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.592   1.665  -0.555  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.378   0.839   0.269  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.689   0.891  -0.457  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.677   1.860   0.100  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.948   1.368  -0.552  1.00  0.00           C  
HETATM   19  O2  UNL     1      -5.028   2.017  -0.657  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.721   0.007  -1.044  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.448  -0.625  -1.851  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.316  -0.140   1.799  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.885  -0.737   1.235  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.530  -1.875   1.186  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.026  -2.449  -0.785  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.907  -1.373  -2.207  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.233  -2.335  -0.873  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.276  -0.848  -1.841  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.241  -1.156   1.153  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.684  -2.764   0.735  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.091  -2.917   0.978  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.409  -0.171   0.834  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.504   1.227   0.475  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.581   2.397  -0.524  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.749   2.396   1.100  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.140   2.628  -0.872  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.796   1.091  -1.482  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.452   1.271   1.302  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.562   1.109  -1.540  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.771   1.756   1.201  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.474   2.911  -0.188  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   16   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7    7   12
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   11
CONECT   10   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   38
CONECT   16   17   39
CONECT   17   18   40   41
CONECT   18   19   19   20
CONECT   20   21   21
END

HMDB0000372
     RDKit          3D
16-Oxoestrone
 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.7943   -0.7892    1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4605   -0.4123   -0.3709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6954   -1.4462   -1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1973   -1.3133   -0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -0.5700    0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469   -0.6104    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385   -1.8370    0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -1.9560    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -0.8544    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -0.9713    0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8378    0.3813    0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.4908    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    1.8468    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5925    1.6649   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778    0.8390    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892    0.8915   -0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    1.8604    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478    1.3676   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    2.0170   -0.6573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7206    0.0072   -1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484   -0.6250   -1.8506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164   -0.1404    1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -0.7373    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.8753    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -2.4488   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071   -1.3733   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -2.3352   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -0.8481   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412   -1.1564    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -2.7642    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -2.9166    0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4088   -0.1712    0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5045    1.2271    0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809    2.3966   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    2.3959    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397    2.6276   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959    1.0913   -1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4518    1.2712    1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5624    1.1085   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    1.7563    1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    2.9110   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  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
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16-Ketoestrone	HMDB
3-Hydroxy-1,3,5(10)-estratriene-16,17-dione	HMDB

Chemical Formula

C₁₈H₂₀O₃

Average Molecular Weight

284.3496

Monoisotopic Molecular Weight

284.141244506

IUPAC Name

(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione

Traditional Name

(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione

CAS Registry Number

1228-73-5

SMILES

C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O

InChI Identifier

InChI=1S/C18H20O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1

InChI Key

ANPHVANSJXDRTP-VLVBFLKRSA-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
3-hydroxysteroid
Hydroxysteroid
16-oxosteroid
17-oxosteroid
Oxosteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Cyclic ketone
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000372)
Cell membrane (HMDB: HMDB0000372)

Biofluid or Excreta

Urine (HMDB: HMDB0000372)

Tissue substructure

Placenta (HMDB: HMDB0000372)
Hepatic tissue (HMDB: HMDB0000372)

Organ

Placenta (HMDB: HMDB0000372)
Liver (HMDB: HMDB0000372)

Cellular substructure

Membrane (HMDB: HMDB0000372)
Extracellular (HMDB: HMDB0000372)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000372)

Source

Endogenous

Endogenous (HMDB: HMDB0000372)

Animal

Animal (HMDB: HMDB0000372)

Exogenous

Food

Food (HMDB: HMDB0000372)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000372)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000372)

Cellular process

Cell signaling (HMDB: HMDB0000372)

System process

Reproduction (HMDB: HMDB0000372)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000372)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000372)

Molecular messenger

Hormone (HMDB: HMDB0000372)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000372)

Emulsifier (HMDB: HMDB0000372)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231 - 235 °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	0.02 g/L	ALOGPS
logP	2.86	ALOGPS
logP	4.15	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.83 m³·mol⁻¹	ChemAxon
Polarizability	31.49 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]+	167.686	31661259
DarkChem	[M-H]-	163.421	31661259
AllCCS	[M+H]+	168.614	32859911
AllCCS	[M-H]-	174.947	32859911
DeepCCS	[M-2H]-	202.524	30932474
DeepCCS	[M+Na]+	177.856	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	165.2	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	174.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16-Oxoestrone	C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O	3743.4	Standard polar	33892256
16-Oxoestrone	C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O	2528.0	Standard non polar	33892256
16-Oxoestrone	C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O	2858.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16-Oxoestrone,1TMS,isomer #1	C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1CC(=O)C2=O	2840.0	Semi standard non polar	33892256
16-Oxoestrone,1TMS,isomer #2	C[C@]12CCC3C4=CC=C(O)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O	2786.0	Semi standard non polar	33892256
16-Oxoestrone,2TMS,isomer #1	C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O	2821.2	Semi standard non polar	33892256
16-Oxoestrone,2TMS,isomer #1	C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O	2729.0	Standard non polar	33892256
16-Oxoestrone,2TMS,isomer #1	C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O	3087.1	Standard polar	33892256
16-Oxoestrone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CCC1C2CC[C@]2(C)C(=O)C(=O)CC12	3080.5	Semi standard non polar	33892256
16-Oxoestrone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O)=CC=C4C3CC[C@]2(C)C1=O	3074.9	Semi standard non polar	33892256
16-Oxoestrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O	3343.8	Semi standard non polar	33892256
16-Oxoestrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O	3181.7	Standard non polar	33892256
16-Oxoestrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O	3317.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0970000000-c33450029c2a510fb1dd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (1 TMS) - 70eV, Positive	splash10-0032-1095000000-28ce684570c9033f6ecb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Positive-QTOF	splash10-000i-0090000000-6d759bc421714d0d2920	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Positive-QTOF	splash10-0a4r-0390000000-d8c66380533ac80c418f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Positive-QTOF	splash10-0gdi-7980000000-4a05c980006c31f9644c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Negative-QTOF	splash10-001i-0090000000-71415abfa8ce5bdff3d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Negative-QTOF	splash10-001i-0090000000-66dbf6c2ee8a27f150f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Negative-QTOF	splash10-0gdi-1090000000-dd632ccd4b6912edb4b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Negative-QTOF	splash10-001i-0090000000-78a425e25a58a7330ede	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Negative-QTOF	splash10-001i-0090000000-ea975f2e73cc3dfd69ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Negative-QTOF	splash10-01sl-0390000000-45c573c062efce8ba045	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Positive-QTOF	splash10-000i-0090000000-5bc7bcd7c5f268094120	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Positive-QTOF	splash10-004r-0590000000-13c3647f4ba51b6998ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Positive-QTOF	splash10-004i-1790000000-7983b1aed115bbdf442d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Liver
Placenta

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

FDB021991

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14441

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5361

PubChem Compound

53477688

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

uffman, Max N. 16-Keto estrogens. (1950), US 2522178 19500912 CAN 45:6349 AN 1951:6349

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 16-Oxoestrone (HMDB0000372)

MOL for HMDB0000372 (16-Oxoestrone)

3D MOL for HMDB0000372 (16-Oxoestrone)

3D SDF for HMDB0000372 (16-Oxoestrone)

3D-SDF for HMDB0000372 (16-Oxoestrone)

PDB for HMDB0000372 (16-Oxoestrone)

3D PDB for HMDB0000372 (16-Oxoestrone)

SMILES for HMDB0000372 (16-Oxoestrone)

INCHI for HMDB0000372 (16-Oxoestrone)

Structure for HMDB0000372 (16-Oxoestrone)

3D Structure for HMDB0000372 (16-Oxoestrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra