NP-MRD: Showing NP-Card for 16a-Hydroxyestrone (NP0000285)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-09 22:32:53 UTC

NP-MRD ID

NP0000285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16a-Hydroxyestrone

Description

16A-Hydroxyestrone or 16alpha-hydroxyestrone (16α-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>
NP0000285

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

Value	Source
16 alpha OHE	ChEBI
16alpha-OHE	ChEBI
16alpha-OHE1	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
16a-OHE	Generator
16Α-ohe	Generator
16a-OHE1	Generator
16Α-ohe1	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 Mass

286.3655 Da

Monoisotopic Mass

286.15689 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000335

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021959

KNApSAcK ID

Not Available

Chemspider ID

103012

KEGG Compound ID

C05300

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

16-Hydroxyestrone

METLIN ID

2580

PubChem Compound

115116

PDB ID

Not Available

ChEBI ID

776

Good Scents ID

Not Available

References

General References

Khan WA, Zaman GS: Detection of 16alpha-Hydroxyestrone-histone 1 Adduct as High-Affinity Antigen for Rheumatoid Arthritis Autoantibodies. Arch Immunol Ther Exp (Warsz). 2018 Oct;66(5):379-388. doi: 10.1007/s00005-018-0512-z. Epub 2018 Apr 30. [PubMed:29713726 ]
Bucala R, Lahita RG, Fishman J, Cerami A: Anti-oestrogen antibodies in users of oral contraceptives and in patients with systemic lupus erythematosus. Clin Exp Immunol. 1987 Jan;67(1):167-75. [PubMed:3621671 ]
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 ]

Showing NP-Card for 16a-Hydroxyestrone (NP0000285)

MOL for NP0000285 (16a-Hydroxyestrone)

3D MOL for NP0000285 (16a-Hydroxyestrone)

3D SDF for NP0000285 (16a-Hydroxyestrone)

3D-SDF for NP0000285 (16a-Hydroxyestrone)

PDB for NP0000285 (16a-Hydroxyestrone)

3D PDB for NP0000285 (16a-Hydroxyestrone)

SMILES for NP0000285 (16a-Hydroxyestrone)

INCHI for NP0000285 (16a-Hydroxyestrone)

Structure for NP0000285 (16a-Hydroxyestrone)

3D Structure for NP0000285 (16a-Hydroxyestrone)