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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000335

Secondary Accession Numbers

HMDB00335

Metabolite Identification

Common Name

16a-Hydroxyestrone

Description

16a-Hydroxyestrone or 16alpha-hydroxyestrone (16alpha-OH-E1 or 16a OHE1), or hydroxyestrone, is an endogenous steroidal estrogen and a major metabolite of estrone and estradiol. 16a-hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16a-hydroxyestrone is considered to be a steroid molecule. 16a-hydroxyestrone is found in all vertebrates. Vertebrates, especially mammals, metabolizes estrogen into two major pathways and one minor. The two major pathways lead to 2-hydroxyestrone and 16a-hydroxyestrone (2-OHE1 and 16a OHE1 respectively). The minor pathway leads to 4-hydroxyestrone (4-OHE1). 2a-hydroxyestrone is considered to be the good metabolite (PMID: 8943806 ) as 2-hydroxyestrone does not stimulate cell growth and it blocks the action of stronger estrogens that may be carcinogenic. 16a-Hydroxyestrone, on the other hand, has a significantly stronger estrogenic activity, and studies show that it may increase the risk of breast cancer. The binding of 16a-hydroxyestrone to the estrogen receptor is reported to be covalent and irreversible (PMID: 3186693 ). A low urinary ratio of 2-hydroxyestrone to 16-alpha-hydroxyestrone is a strong predictor of breast cancer risk among women (PMID: 19502596 ).

Structure

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

HMDB0000335
     RDKit          3D
16a-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.1360   -0.6444   -1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.4525   -0.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5242    1.6546   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    1.4148   -1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    0.7096    0.0434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9570    0.3544   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567    1.1514   -0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940    0.8325   -1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6341   -0.3048   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9746   -0.6629   -0.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -1.1179    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.7885    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.7069    1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303   -1.1841    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -0.4927    0.4916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6092    0.0393    0.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6028   -0.8978    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8993   -0.0951    1.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0337    0.8208    2.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    0.6815   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4593    1.3873   -0.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -0.5195   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -1.6552   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -0.5407   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179    1.9066   -2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928    2.4975   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    0.9205   -2.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    2.4323   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    1.4414    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085    2.0665   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    1.4578   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5851   -0.1051   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926   -2.0102    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -2.6964    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -1.9644    2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5006   -0.5429    2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -2.0562    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -1.1840   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.9600    1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -1.8422    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -1.1195    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634   -0.7591    1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340    1.7091    1.9746 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
  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  1  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  1
  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  6
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
M  END

16a-Hydroxyestrone.mol
  Mrv1652305261923522D          

 24 27  0  0  0  0            999 V2000
   -2.4762   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0961   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.3052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808    0.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1357    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0961    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0473   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  1  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 20  2  0  0  0  0
 12 21  1  6  0  0  0
 19 22  1  6  0  0  0
  9 23  1  1  0  0  0
 10 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000335

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1

> <INCHI_KEY>
WPOCIZJTELRQMF-QFXBJFAPSA-N

> <FORMULA>
C18H22O3

> <MOLECULAR_WEIGHT>
286.3655

> <EXACT_MASS>
286.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.06292129722553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.4379631133333346

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.38257874741176

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.326567997010477

> <JCHEM_PKA_STRONGEST_BASIC>
-3.506418620839579

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
80.57459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000335
     RDKit          3D
16a-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.1360   -0.6444   -1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.4525   -0.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5242    1.6546   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    1.4148   -1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    0.7096    0.0434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9570    0.3544   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567    1.1514   -0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940    0.8325   -1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6341   -0.3048   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9746   -0.6629   -0.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -1.1179    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.7885    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.7069    1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303   -1.1841    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -0.4927    0.4916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6092    0.0393    0.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6028   -0.8978    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8993   -0.0951    1.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0337    0.8208    2.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    0.6815   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4593    1.3873   -0.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -0.5195   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -1.6552   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -0.5407   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179    1.9066   -2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928    2.4975   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    0.9205   -2.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    2.4323   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    1.4414    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085    2.0665   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    1.4578   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5851   -0.1051   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926   -2.0102    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -2.6964    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -1.9644    2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5006   -0.5429    2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -2.0562    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -1.1840   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.9600    1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -1.8422    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -1.1195    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634   -0.7591    1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340    1.7091    1.9746 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
  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  1  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  1
  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  6
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 16a-Hydroxyestrone.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.622  -2.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.956  -3.280   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.622  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.289  -0.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.289  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.955  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.621  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.713  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.713  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.046  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.511  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.416   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.511   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.987   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.046   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.046   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.713   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.621   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.621  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.955  -0.970   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.956   0.570   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -0.621  -1.740   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.713   0.570   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.046  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3   20                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19   23                                             
CONECT   10    9   11   15   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20   22                                             
CONECT   20   19    4    6                                                  
CONECT   21   12                                                            
CONECT   22   19                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000335
HETATM    1  C1  UNL     1      -2.136  -0.644  -1.537  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.264   0.452  -0.510  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.524   1.655  -0.985  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.064   1.415  -1.115  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.569   0.710   0.043  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.957   0.354  -0.214  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.757   1.151  -0.989  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.094   0.833  -1.250  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.634  -0.305  -0.724  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.975  -0.663  -0.962  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.854  -1.118   0.053  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.514  -0.788   0.309  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.741  -1.707   1.149  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.430  -1.184   1.634  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.273  -0.493   0.492  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.609   0.039   0.817  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.603  -0.898   1.378  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.899  -0.095   1.168  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.034   0.821   2.227  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.638   0.681  -0.074  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.459   1.387  -0.618  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.218  -0.519  -2.116  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.146  -1.655  -1.107  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.990  -0.541  -2.265  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.918   1.907  -2.008  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.693   2.497  -0.287  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.226   0.920  -2.080  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.425   2.432  -1.174  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.555   1.441   0.905  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.408   2.066  -1.442  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.724   1.458  -1.859  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.585  -0.105  -1.522  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.293  -2.010   0.461  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.553  -2.696   0.649  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.359  -1.964   2.053  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.501  -0.543   2.534  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.204  -2.056   1.916  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.307  -1.184  -0.359  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.594   0.960   1.431  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.723  -1.842   0.853  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.459  -1.119   2.454  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.763  -0.759   1.086  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.634   1.709   1.975  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   20   42
CONECT   19   43
CONECT   20   21   21
END

HMDB0000335
     RDKit          3D
16a-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.1360   -0.6444   -1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.4525   -0.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5242    1.6546   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    1.4148   -1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    0.7096    0.0434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9570    0.3544   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567    1.1514   -0.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940    0.8325   -1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6341   -0.3048   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9746   -0.6629   -0.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -1.1179    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.7885    0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.7069    1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303   -1.1841    1.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -0.4927    0.4916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6092    0.0393    0.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6028   -0.8978    1.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8993   -0.0951    1.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0337    0.8208    2.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    0.6815   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4593    1.3873   -0.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -0.5195   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -1.6552   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -0.5407   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179    1.9066   -2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928    2.4975   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    0.9205   -2.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    2.4323   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    1.4414    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085    2.0665   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    1.4578   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5851   -0.1051   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926   -2.0102    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -2.6964    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -1.9644    2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5006   -0.5429    2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -2.0562    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -1.1840   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.9600    1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -1.8422    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -1.1195    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634   -0.7591    1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340    1.7091    1.9746 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
  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  1  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  1
  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  6
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16 alpha OHE	ChEBI
3,16alpha-Dihydroxy-1,3,5(10)-estratrien-17-one	ChEBI
3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one	ChEBI
Estra-1,3,5(10)-triene-3,16alpha-diol-17-one	ChEBI
16 a OHE	Generator
16 Α ohe	Generator
3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one	Generator
3,16Α-dihydroxy-1,3,5(10)-estratrien-17-one	Generator
3,16a-Dihydroxyestra-1,3,5(10)-trien-17-one	Generator
3,16Α-dihydroxyestra-1,3,5(10)-trien-17-one	Generator
Estra-1,3,5(10)-triene-3,16a-diol-17-one	Generator
Estra-1,3,5(10)-triene-3,16α-diol-17-one	Generator
16 alpha-Hydroxyestrone	HMDB
3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-one	HMDB
16 beta-Hydroxyestrone	HMDB
16-alpha-Hydroxyestrone	HMDB
16-Hydroxyestrone	HMDB

Chemical Formula

C₁₈H₂₂O₃

Average Molecular Weight

286.3655

Monoisotopic Molecular Weight

286.15689457

IUPAC Name

(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

Traditional Name

(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

CAS Registry Number

566-76-7

SMILES

[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

InChI Identifier

InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1

InChI Key

WPOCIZJTELRQMF-QFXBJFAPSA-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
17-oxosteroid
Oxosteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Ketone
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

16alpha-hydroxy steroid (CHEBI:776 )
C18 steroids (estrogens) and derivatives (LMST02010041 )

Ontology

Not Available

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	0.047 g/L	ALOGPS
logP	2.45	ALOGPS
logP	3.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.57 m³·mol⁻¹	ChemAxon
Polarizability	32.06 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]+	168.019	31661259
DarkChem	[M-H]-	166.004	31661259
AllCCS	[M+H]+	170.512	32859911
AllCCS	[M-H]-	175.495	32859911
DeepCCS	[M-2H]-	212.31	30932474
DeepCCS	[M+Na]+	187.223	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.6	32859911
AllCCS	[M+Na]+	174.5	32859911
AllCCS	[M-H]-	175.5	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16a-Hydroxyestrone	[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3438.6	Standard polar	33892256
16a-Hydroxyestrone	[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2824.6	Standard non polar	33892256
16a-Hydroxyestrone	[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2829.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16a-Hydroxyestrone,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O	2768.0	Semi standard non polar	33892256
16a-Hydroxyestrone,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O)C2=O	2786.1	Semi standard non polar	33892256
16a-Hydroxyestrone,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C	2768.1	Semi standard non polar	33892256
16a-Hydroxyestrone,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O	2875.1	Semi standard non polar	33892256
16a-Hydroxyestrone,2TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2779.4	Semi standard non polar	33892256
16a-Hydroxyestrone,2TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C	2839.0	Semi standard non polar	33892256
16a-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2905.4	Semi standard non polar	33892256
16a-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2783.1	Standard non polar	33892256
16a-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2899.0	Standard polar	33892256
16a-Hydroxyestrone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)C1=O	3049.5	Semi standard non polar	33892256
16a-Hydroxyestrone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@H](O)C[C@@H]12	3088.5	Semi standard non polar	33892256
16a-Hydroxyestrone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C	3043.6	Semi standard non polar	33892256
16a-Hydroxyestrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]12	3412.8	Semi standard non polar	33892256
16a-Hydroxyestrone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]2C1	3287.1	Semi standard non polar	33892256
16a-Hydroxyestrone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	3331.5	Semi standard non polar	33892256
16a-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1	3616.3	Semi standard non polar	33892256
16a-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1	3466.0	Standard non polar	33892256
16a-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1	3214.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (1 MEOX; 2 TMS)	splash10-0019-3941100000-3a930f8cc95b733c8653	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (1 MEOX; 2 TMS)	splash10-0019-3941100000-3e52ec60bd9142c09b74	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (Non-derivatized)	splash10-0019-3941100000-3a930f8cc95b733c8653	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (Non-derivatized)	splash10-0019-3941100000-3e52ec60bd9142c09b74	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-2690000000-4da4066a9998d4bb7152	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positive	splash10-0gj1-1193300000-a36ac7539d25b407ca9f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyestrone GC-MS (TBDMS_2_3) - 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 - 16a-Hydroxyestrone 10V, Positive-QTOF	splash10-000i-0090000000-ea49b0e7c1a26f8807b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 20V, Positive-QTOF	splash10-0ap0-0490000000-7a9632ca2f7369b28ad3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 40V, Positive-QTOF	splash10-0gb9-7980000000-f674402195ec376faeb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 10V, Negative-QTOF	splash10-000i-0090000000-91f32a5e866ea149a4a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 20V, Negative-QTOF	splash10-000i-0090000000-f8524ff8a5fae66251ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 40V, Negative-QTOF	splash10-02dl-1090000000-5ac386a35fc2bb3cc1f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 10V, Positive-QTOF	splash10-000i-0090000000-8269f9806e3a6460adb9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 20V, Positive-QTOF	splash10-00ks-0590000000-2d8e09d2baef368efec1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 40V, Positive-QTOF	splash10-00dj-0920000000-bce8e0246e58d9e59bbd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 10V, Negative-QTOF	splash10-000i-0090000000-fcaf0435bbf678a207f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 20V, Negative-QTOF	splash10-000i-0090000000-48bccddc063fe7e2f998	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyestrone 40V, Negative-QTOF	splash10-02di-0090000000-080f7d164203318ad338	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Estrone Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00078 (0.00076-0.00081) uM	Adult (>18 years old)	Female	Normal	14569192	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000817 (0.0008-0.00084) uM	Adult (>18 years old)	Female	Breast cancer	14569192	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Cauley JA, Zmuda JM, Danielson ME, Ljung BM, Bauer DC, Cummings SR, Kuller LH: Estrogen metabolites and the risk of breast cancer in older women. Epidemiology. 2003 Nov;14(6):740-4. [PubMed:14569192 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021959

KNApSAcK ID

Not Available

Chemspider ID

103012

KEGG Compound ID

C05300

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

2580

PubChem Compound

115116

PDB ID

Not Available

ChEBI ID

776

Food Biomarker Ontology

Not Available

VMH ID

C05300

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Knuppen, R.; Breuer, H. Biogenesis of 11b-hydroxyestrone and 16a-hydroxyestrone by adrenal tissue. Biochimica et Biophysica Acta (1962), 58 147-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Bradlow HL, Telang NT, Sepkovic DW, Osborne MP: 2-hydroxyestrone: the 'good' estrogen. J Endocrinol. 1996 Sep;150 Suppl:S259-65. [PubMed:8943806 ]
Swaneck GE, Fishman J: Covalent binding of the endogenous estrogen 16 alpha-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intranuclear localization. Proc Natl Acad Sci U S A. 1988 Nov;85(21):7831-5. doi: 10.1073/pnas.85.21.7831. [PubMed:3186693 ]
Im A, Vogel VG, Ahrendt G, Lloyd S, Ragin C, Garte S, Taioli E: Urinary estrogen metabolites in women at high risk for breast cancer. Carcinogenesis. 2009 Sep;30(9):1532-5. doi: 10.1093/carcin/bgp139. Epub 2009 Jun 5. [PubMed:19502596 ]

Enzymes

Enzyme Details

1. Estradiol 17-beta-dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:: HSD17B2
Uniprot ID:: P37059
Molecular weight:: 42784.75

Enzyme Details

2. Estradiol 17-beta-dehydrogenase 8

General function:: Involved in oxidoreductase activity
Specific function:: NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:: HSD17B8
Uniprot ID:: Q92506
Molecular weight:: 26973.56

Enzyme Details

3. Estradiol 17-beta-dehydrogenase 1

General function:: Involved in estradiol 17-beta-dehydrogenase activity
Specific function:: Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:: HSD17B1
Uniprot ID:: P14061
Molecular weight:: 34949.715

Enzyme Details

4. 3-keto-steroid reductase

General function:: Involved in oxidoreductase activity
Specific function:: Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:: HSD17B7
Uniprot ID:: P56937
Molecular weight:: 38205.77

Showing metabocard for 16a-Hydroxyestrone (HMDB0000335)

MOL for HMDB0000335 (16a-Hydroxyestrone)

3D MOL for HMDB0000335 (16a-Hydroxyestrone)

3D SDF for HMDB0000335 (16a-Hydroxyestrone)

3D-SDF for HMDB0000335 (16a-Hydroxyestrone)

PDB for HMDB0000335 (16a-Hydroxyestrone)

3D PDB for HMDB0000335 (16a-Hydroxyestrone)

SMILES for HMDB0000335 (16a-Hydroxyestrone)

INCHI for HMDB0000335 (16a-Hydroxyestrone)

Structure for HMDB0000335 (16a-Hydroxyestrone)

3D Structure for HMDB0000335 (16a-Hydroxyestrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes