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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

HMDB0000343

Secondary Accession Numbers

HMDB00343

Metabolite Identification

Common Name

2-Hydroxyestrone

Description

2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. 2-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, 2-Hydroxyestrone is considered to be a steroid molecule. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body. 2-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 steroid metabolite (PMID: 8943806 ) as 2-hydroxyestrone does not stimulate cell growth and it blocks the action of stronger estrogens that may be carcinogenic. 2-hydroxyestrone is not significantly uterotrophic, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16a-hydroxyestrone, estriol, 4-hydroxyestradiol, and 4-hydroxyestrone all are. 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

HMDB0000343
     RDKit          3D
2-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.3935    0.7048   -1.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4244    0.6764   -0.1902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7709    1.8803    0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776    1.8377    0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    0.5185    0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7531    0.3842    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130    1.3846   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    1.1883   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    2.1845   -1.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919   -0.0457   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -0.3371   -0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -1.0760    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197   -0.8384    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -1.8976    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.9588    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.6442    0.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7935   -0.5488    0.4182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7194   -1.6258    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0648   -0.9868    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8401    0.4954    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574    1.3401    0.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434   -0.1326   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751    0.7902   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    1.6321   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921    2.7638   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    2.0254    1.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605    2.5492    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    2.2612   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.3011    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249    2.3600   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5849    2.1263   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3262    0.3493   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -2.0351    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445   -1.6788    2.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469   -2.8824    1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704   -2.5786    0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4286   -2.5975   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.5149   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8451   -0.4263    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -2.5750    0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -1.8517   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658   -1.3396   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -1.1815    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 16  5  1  0
 13  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
M  END

2-Hydroxyestrone.mol
  Mrv1652305261923542D          

 24 27  0  0  0  0            999 V2000
   -2.0637   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    0.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -0.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -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
  3 21  1  0  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>
HMDB0000343

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1

> <INCHI_KEY>
SWINWPBPEKHUOD-JPVZDGGYSA-N

> <FORMULA>
C18H22O3

> <MOLECULAR_WEIGHT>
286.3655

> <EXACT_MASS>
286.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.23089717888351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
4.005463712333334

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.072549466131083

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.670288349087553

> <JCHEM_PKA_STRONGEST_BASIC>
-6.253118360545746

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
81.06329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000343
     RDKit          3D
2-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.3935    0.7048   -1.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4244    0.6764   -0.1902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7709    1.8803    0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776    1.8377    0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    0.5185    0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7531    0.3842    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130    1.3846   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    1.1883   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    2.1845   -1.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919   -0.0457   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -0.3371   -0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -1.0760    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197   -0.8384    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -1.8976    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.9588    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.6442    0.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7935   -0.5488    0.4182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7194   -1.6258    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0648   -0.9868    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8401    0.4954    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574    1.3401    0.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434   -0.1326   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751    0.7902   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    1.6321   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921    2.7638   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    2.0254    1.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605    2.5492    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    2.2612   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.3011    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249    2.3600   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5849    2.1263   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3262    0.3493   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -2.0351    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445   -1.6788    2.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469   -2.8824    1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704   -2.5786    0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4286   -2.5975   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.5149   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8451   -0.4263    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -2.5750    0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -1.8517   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658   -1.3396   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -1.1815    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 16  5  1  0
 13  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Hydroxyestrone.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.816   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.186  -0.200   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4   21                                                  
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                                                       
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    3                                                            
CONECT   22   19                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000343
HETATM    1  C1  UNL     1      -2.394   0.705  -1.675  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.424   0.676  -0.190  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.771   1.880   0.408  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.278   1.838   0.424  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.327   0.518   0.692  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.753   0.384   0.358  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.513   1.385  -0.196  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.872   1.188  -0.489  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.630   2.184  -1.042  1.00  0.00           O  
HETATM   10  C9  UNL     1       4.392  -0.046  -0.194  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.721  -0.337  -0.447  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.630  -1.076   0.371  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.320  -0.838   0.637  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.430  -1.898   1.249  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.183  -1.959   0.419  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.386  -0.644   0.005  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.793  -0.549   0.418  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.719  -1.626   0.013  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.065  -0.987   0.331  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.840   0.495   0.237  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.657   1.340   0.467  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.943  -0.133  -2.139  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.375   0.790  -2.108  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.929   1.632  -1.999  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.092   2.764  -0.184  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.207   2.025   1.425  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.061   2.549   1.208  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.108   2.261  -0.530  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.220   0.301   1.794  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.125   2.360  -0.434  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.585   2.126  -1.276  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.326   0.349  -0.849  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.076  -2.035   0.589  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.245  -1.679   2.310  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.947  -2.882   1.165  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.570  -2.579   0.985  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.429  -2.598  -0.479  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.195  -0.515  -1.077  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.845  -0.426   1.517  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.570  -2.575   0.570  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.720  -1.852  -1.064  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.866  -1.340  -0.315  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.251  -1.182   1.421  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   16   29
CONECT    6    7    7   13
CONECT    7    8   30
CONECT    8    9   10   10
CONECT    9   31
CONECT   10   11   12
CONECT   11   32
CONECT   12   13   13   33
CONECT   13   14
CONECT   14   15   34   35
CONECT   15   16   36   37
CONECT   16   17   38
CONECT   17   18   39
CONECT   18   19   40   41
CONECT   19   20   42   43
CONECT   20   21   21
END

HMDB0000343
     RDKit          3D
2-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.3935    0.7048   -1.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4244    0.6764   -0.1902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7709    1.8803    0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776    1.8377    0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    0.5185    0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7531    0.3842    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130    1.3846   -0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    1.1883   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301    2.1845   -1.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919   -0.0457   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -0.3371   -0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -1.0760    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197   -0.8384    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -1.8976    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.9588    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3856   -0.6442    0.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7935   -0.5488    0.4182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7194   -1.6258    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0648   -0.9868    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8401    0.4954    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574    1.3401    0.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434   -0.1326   -2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751    0.7902   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289    1.6321   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921    2.7638   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    2.0254    1.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605    2.5492    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    2.2612   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.3011    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249    2.3600   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5849    2.1263   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3262    0.3493   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -2.0351    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445   -1.6788    2.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469   -2.8824    1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704   -2.5786    0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4286   -2.5975   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.5149   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8451   -0.4263    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -2.5750    0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -1.8517   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658   -1.3396   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -1.1815    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 16  5  1  0
 13  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Dihydroxyestra-1,3,5(10)-trien-17-one	HMDB
2-OHE1	HMDB
Catecholestrone	HMDB
2-Hydroxyestrone, 4-(14)C-labeled	MeSH, HMDB

Chemical Formula

C₁₈H₂₂O₃

Average Molecular Weight

286.3655

Monoisotopic Molecular Weight

286.15689457

IUPAC Name

(1S,10R,11S,15S)-4,5-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,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

CAS Registry Number

362-06-1

SMILES

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

InChI Identifier

InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1

InChI Key

SWINWPBPEKHUOD-JPVZDGGYSA-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
2-hydroxysteroid
Hydroxysteroid
17-oxosteroid
Oxosteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

2-hydroxy steroid (CHEBI:1156 )
C18 steroids (estrogens) and derivatives (C05298 )
C18 steroids (estrogens) and derivatives (LMST02010032 )

Ontology

Physiological effect

Health effect

Observation

Pregnancy (HMDB: HMDB0000343)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 663967)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 8478958)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000343)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000343)

Source

Endogenous

Endogenous (HMDB: HMDB0000343)

Animal

Animal (HMDB: HMDB0000343)

Exogenous

Food

Food (HMDB: HMDB0000343)

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000343)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000343)

Molecular messenger

Hormone (HMDB: HMDB0000343)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000343)

Pharmaceutical industry

Biomarker

Pregnancy (MarkerDB: MDB00000149)

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	0.023 g/L	ALOGPS
logP	3.03	ALOGPS
logP	4.01	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-6.3	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	81.06 m³·mol⁻¹	ChemAxon
Polarizability	32.23 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]+	169.91	31661259
DarkChem	[M-H]-	162.517	31661259
AllCCS	[M+H]+	170.183	32859911
AllCCS	[M-H]-	175.807	32859911
DeepCCS	[M-2H]-	210.299	30932474
DeepCCS	[M+Na]+	185.491	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	175.8	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.19 minutes	32390414
Predicted by Siyang on May 30, 2022	12.724 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2064.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	573.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1133.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	438.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1323.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	282.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	98.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyestrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3	3682.2	Standard polar	33892256
2-Hydroxyestrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3	2797.2	Standard non polar	33892256
2-Hydroxyestrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3	2996.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyestrone,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	2832.0	Semi standard non polar	33892256
2-Hydroxyestrone,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CCC2=O	2818.9	Semi standard non polar	33892256
2-Hydroxyestrone,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC(O)=C(O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2770.8	Semi standard non polar	33892256
2-Hydroxyestrone,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	2866.8	Semi standard non polar	33892256
2-Hydroxyestrone,2TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2772.8	Semi standard non polar	33892256
2-Hydroxyestrone,2TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2743.1	Semi standard non polar	33892256
2-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2752.2	Semi standard non polar	33892256
2-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2726.3	Standard non polar	33892256
2-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2953.2	Standard polar	33892256
2-Hydroxyestrone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2	3108.4	Semi standard non polar	33892256
2-Hydroxyestrone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12	3100.7	Semi standard non polar	33892256
2-Hydroxyestrone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O)=C(O)C=C4[C@H]3CC[C@]12C	3045.8	Semi standard non polar	33892256
2-Hydroxyestrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2	3393.7	Semi standard non polar	33892256
2-Hydroxyestrone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C4[C@H]3CC[C@]12C	3270.5	Semi standard non polar	33892256
2-Hydroxyestrone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C	3241.9	Semi standard non polar	33892256
2-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C	3410.4	Semi standard non polar	33892256
2-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C	3306.1	Standard non polar	33892256
2-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4[C@H]3CC[C@]12C	3282.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vr-1980000000-fe43c8c5b3a4d07200c9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positive	splash10-016r-5449800000-4e55823f57ec07ec0913	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestrone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyestrone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0w2i-0798000000-41a67b9322f4b2428372	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyestrone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0f92-1920000000-1852b9bae72a1d8a9dc8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyestrone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0zfs-2930000000-5911e48b958d80b00d92	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Positive-QTOF	splash10-000i-0190000000-644377b19800b89d92e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Positive-QTOF	splash10-0a4r-0790000000-1a42c791a4695a613eac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Positive-QTOF	splash10-0zfr-6690000000-645e51e9feba8eee90e2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Negative-QTOF	splash10-000i-0090000000-42c0dd5f87119fd72c44	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Negative-QTOF	splash10-000i-0090000000-6509e54bf81b0caae551	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Negative-QTOF	splash10-05mo-1090000000-ff9544e7658c8bae039d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Positive-QTOF	splash10-000i-0090000000-c6a01b40f4853dcb1f7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Positive-QTOF	splash10-07br-0590000000-21461e356ecdcb3c08c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Positive-QTOF	splash10-0200-1910000000-030e5b518db4e2ad41fd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 10V, Negative-QTOF	splash10-000i-0090000000-fcaf0435bbf678a207f7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 20V, Negative-QTOF	splash10-000i-0090000000-3a4481ab24130f65a893	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestrone 40V, Negative-QTOF	splash10-0kor-0190000000-13b24a7b3a6558370742	2021-09-23	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
Urine

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	0.00024 (0.00017-0.00033) uM	Adult (>18 years old)	Female	Normal	663967	details
Blood	Detected and Quantified	0.00017 (0.00015-0.00022) uM	Adult (>18 years old)	Male	Normal	663967	details
Blood	Detected and Quantified	0.0001 (0.000070-0.00013) uM	Children (1-13 years old)	Both	Normal	663967	details
Urine	Detected and Quantified	0.0015 +/- 0.0013 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8478958	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00052 (0.00036-0.00076) uM	Adult (>18 years old)	Female	Pregnancy	663967	details

Associated Disorders and Diseases

Disease References

Pregnancy
Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed:663967 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021966

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05298

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hydroxyestrone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

1156

Food Biomarker Ontology

Not Available

VMH ID

C05298

MarkerDB ID

MDB00000149

Good Scents ID

Not Available

References

Synthesis Reference

Kovacs, Katalin; Rakonczay, Z.; Matkovics, B. Steroids. XXIII. Synthesis of 2- and 4-hydroxy and 2,4-dihydroxy derivatives of estrone and estradiol. Acta Physica et Chemica (1973), 19(3), 287-90.

Material Safety Data Sheet (MSDS)

Not Available

General References

Brooks JD, Ward WE, Lewis JE, Hilditch J, Nickell L, Wong E, Thompson LU: Supplementation with flaxseed alters estrogen metabolism in postmenopausal women to a greater extent than does supplementation with an equal amount of soy. Am J Clin Nutr. 2004 Feb;79(2):318-25. [PubMed:14749240 ]
Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]
Numazawa M, Kimura K, Nagaoka M, Kambegawa A: Radioimmunoassay of 2-hydroxyesterone using antisera raised against antigenic complexes obtained by convenient methods. Chem Pharm Bull (Tokyo). 1989 Jun;37(6):1561-3. [PubMed:2776239 ]
Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed:663967 ]
Xu X, Keefer LK, Waterhouse DJ, Saavedra JE, Veenstra TD, Ziegler RG: Measuring seven endogenous ketolic estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2004 Oct 1;76(19):5829-36. [PubMed:15456304 ]
Bradlow HL, Telang NT, Sepkovic DW, Osborne MP: 2-hydroxyestrone: the 'good' estrogen. J Endocrinol. 1996 Sep;150 Suppl:S259-65. [PubMed:8943806 ]
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. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

2-Hydroxyestrone + S-Adenosylmethionine → 2-Methoxyestrone + S-Adenosylhomocysteine	details

Showing metabocard for 2-Hydroxyestrone (HMDB0000343)

MOL for HMDB0000343 (2-Hydroxyestrone)

3D MOL for HMDB0000343 (2-Hydroxyestrone)

3D SDF for HMDB0000343 (2-Hydroxyestrone)

3D-SDF for HMDB0000343 (2-Hydroxyestrone)

PDB for HMDB0000343 (2-Hydroxyestrone)

3D PDB for HMDB0000343 (2-Hydroxyestrone)

SMILES for HMDB0000343 (2-Hydroxyestrone)

INCHI for HMDB0000343 (2-Hydroxyestrone)

Structure for HMDB0000343 (2-Hydroxyestrone)

3D Structure for HMDB0000343 (2-Hydroxyestrone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions