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enzymes (3) Show 3 proteins

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

HMDB0000338

Secondary Accession Numbers

HMDB0003962
HMDB00338
HMDB03962

Metabolite Identification

Common Name

2-Hydroxyestradiol

Description

2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17beta-triol, is an endogenous steroid, catechol estrogen. 2-Hydroxyestradiol 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-hydroxyestradiol is considered to be a steroid molecule. It is a metabolite of estradiol, as well as a positional isomer of estriol. Transformation of estradiol to 2-hydroxyestradiol is a major metabolic pathway of estradiol in the liver. 2-Hydroxyestradiol is generated from estradiol via several cytochrome P450 enzymes. Specifically, CYP1A2 and CYP3A4 are the major enzymes catalyzing the 2-hydroxylation of estradiol. Conversion of estradiol into 2-hydroxyestradiol has been detected in the liver, uterus, breast, kidney, brain, and pituitary gland, as well as the placenta. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. 2-Hydroxyestradiol has approximately 7% and 11% of the affinity of estradiol at the estrogen receptors (ERs) ERalpha and ERbeta, respectively (PMID: 9048584 ). 2-Hydroxyestradiol is a catechol estrogen and in this regard bears some structural resemblance to the catecholamines dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) (PMID: 447670 ). In accordance, 2-hydroxyestradiol has been found to interact with catecholamine systems. The steroid is known to compete with catecholamines for binding to catechol O-methyltransferase and tyrosine hydroxylase and to competitively inhibit these enzymes (PMID: 447670 ). Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neurotransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688 ).

Structure

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

HMDB0000338
     RDKit          3D
2-Hydroxyestradiol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.4679    1.5389   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.5634    0.5693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2644    1.1355    1.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    0.8123    1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -0.2763    0.5597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9942   -0.1630    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9141    0.3212    1.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    0.4610    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1651    0.9523    1.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.0874   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9549    0.1986   -0.9463 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6895   -0.4055   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621   -0.5354   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -1.0622   -2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.6060   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -0.4791   -0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6638   -0.7676    0.0600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7733   -1.2460   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934   -0.8584    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    0.0954    1.1207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4397    1.1304    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359    1.1365   -1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    2.4285   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    1.9560   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    2.2595    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833    0.8651    2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482    0.5807    2.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642    1.7239    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.2404    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6231    0.6196    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1489    1.0866    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814    0.5425   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -0.6964   -2.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -1.8902   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -0.2243   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.4738   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -1.8193   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701    0.4435   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -1.4161    0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -0.8369   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -2.3723   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7627   -0.3873   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761   -1.7560    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785   -0.4142    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355    1.9880    1.5038 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  1  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
 20 44  1  1
 21 45  1  0
M  END

2-Hydroxyestradiol.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  2  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  1  1  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>
HMDB0000338

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O3/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/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

> <INCHI_KEY>
DILDHNKDVHLEQB-XSSYPUMDSA-N

> <FORMULA>
C18H24O3

> <MOLECULAR_WEIGHT>
288.3814

> <EXACT_MASS>
288.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.08384555533665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
3.4419360066666673

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.072616959092134

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.670359586392452

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839974157007265

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
81.88559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000338
     RDKit          3D
2-Hydroxyestradiol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.4679    1.5389   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.5634    0.5693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2644    1.1355    1.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    0.8123    1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -0.2763    0.5597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9942   -0.1630    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9141    0.3212    1.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    0.4610    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1651    0.9523    1.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.0874   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9549    0.1986   -0.9463 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6895   -0.4055   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621   -0.5354   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -1.0622   -2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.6060   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -0.4791   -0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6638   -0.7676    0.0600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7733   -1.2460   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934   -0.8584    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    0.0954    1.1207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4397    1.1304    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359    1.1365   -1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    2.4285   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    1.9560   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    2.2595    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833    0.8651    2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482    0.5807    2.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642    1.7239    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.2404    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6231    0.6196    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1489    1.0866    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814    0.5425   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -0.6964   -2.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -1.8902   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -0.2243   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.4738   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -1.8193   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701    0.4435   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -1.4161    0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -0.8369   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -2.3723   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7627   -0.3873   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761   -1.7560    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785   -0.4142    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355    1.9880    1.5038 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  1  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
 20 44  1  1
 21 45  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Hydroxyestradiol.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    HMDB0000338
HETATM    1  C1  UNL     1      -2.468   1.539  -0.534  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.179   0.563   0.569  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.264   1.136   1.581  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.162   0.812   1.494  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.586  -0.276   0.560  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.994  -0.163   0.134  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.914   0.321   1.038  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.266   0.461   0.716  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.165   0.952   1.653  1.00  0.00           O  
HETATM   10  C9  UNL     1       4.630   0.087  -0.557  1.00  0.00           C  
HETATM   11  O2  UNL     1       5.955   0.199  -0.946  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.689  -0.405  -1.475  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.362  -0.535  -1.138  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.412  -1.062  -2.148  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.154  -1.606  -1.454  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.367  -0.479  -0.604  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.664  -0.768   0.060  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.773  -1.246  -0.765  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.993  -0.858   0.047  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.510   0.095   1.121  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.440   1.130   1.205  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.336   1.137  -1.544  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.781   2.429  -0.430  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.501   1.956  -0.483  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.393   2.259   1.550  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.683   0.865   2.597  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.548   0.581   2.531  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.764   1.724   1.198  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.525  -1.240   1.150  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.623   0.620   2.056  1.00  0.00           H  
HETATM   31  H10 UNL     1       6.149   1.087   1.513  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.681   0.542  -0.343  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.003  -0.696  -2.483  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.818  -1.890  -2.732  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.100  -0.224  -2.804  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.430  -2.474  -0.850  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.602  -1.819  -2.237  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.370   0.444  -1.184  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.547  -1.416   0.963  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.793  -0.837  -1.783  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.717  -2.372  -0.831  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.763  -0.387  -0.602  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.376  -1.756   0.567  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.379  -0.414   2.097  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.036   1.988   1.504  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   44
CONECT   21   45
END

HMDB0000338
     RDKit          3D
2-Hydroxyestradiol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.4679    1.5389   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.5634    0.5693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2644    1.1355    1.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    0.8123    1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -0.2763    0.5597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9942   -0.1630    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9141    0.3212    1.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    0.4610    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1651    0.9523    1.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299    0.0874   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9549    0.1986   -0.9463 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6895   -0.4055   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621   -0.5354   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -1.0622   -2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.6060   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -0.4791   -0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6638   -0.7676    0.0600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7733   -1.2460   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934   -0.8584    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    0.0954    1.1207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4397    1.1304    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359    1.1365   -1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807    2.4285   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    1.9560   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3934    2.2595    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833    0.8651    2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482    0.5807    2.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642    1.7239    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.2404    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6231    0.6196    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1489    1.0866    1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814    0.5425   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029   -0.6964   -2.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -1.8902   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004   -0.2243   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.4738   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -1.8193   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701    0.4435   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -1.4161    0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -0.8369   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -2.3723   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7627   -0.3873   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761   -1.7560    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785   -0.4142    2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355    1.9880    1.5038 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  1  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
 20 44  1  1
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(17beta)-Estra-1,3,5(10)-triene-2,3,17-triol	ChEBI
2-Hydroxyestradiol-17beta	ChEBI
2-OH-e2	ChEBI
2-OH-Estradiol	ChEBI
(17b)-Estra-1,3,5(10)-triene-2,3,17-triol	Generator
(17Β)-estra-1,3,5(10)-triene-2,3,17-triol	Generator
2-Hydroxyestradiol-17b	Generator
2-Hydroxyestradiol-17β	Generator
(17b)-Estra-1,3, 5(10)-triene-2,3,17-triol	HMDB
(17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triol	HMDB
1,3,5(10)-Estratriene-2,3,17Beta-triol	HMDB
17beta-2-Hydroxyestradiol	HMDB
2,3,17b-Trihydroxyestra-1,3,5(10)-triene	HMDB
2-Hydroxy-17beta-estradiol	HMDB
2-Hydroxy-estradiol	HMDB
ECS	HMDB
Estra-1,3,5 (10)-triene-2,3,17.beta.-triol	HMDB
Estra-1,3,5(10)-triene-2,3,17-beta-triol	HMDB
Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0)	HMDB
Estra-1,3,5(10)-triene-2,3,17b-triol	HMDB
Estra-1,3,5(10)-triene-2,3,17beta-triol	HMDB
2-Hydroxyestradiol-17 alpha	HMDB
2-Hydroxyestradiol-17 beta	HMDB
2-Hydroxyestradiol, (17alpha)-isomer	HMDB
2-Hydroxyestradiol, 4-(14)C-labeled	HMDB

Chemical Formula

C₁₈H₂₄O₃

Average Molecular Weight

288.3814

Monoisotopic Molecular Weight

288.172544634

IUPAC Name

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

Traditional Name

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

CAS Registry Number

362-05-0

SMILES

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

InChI Identifier

InChI=1S/C18H24O3/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/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

InChI Key

DILDHNKDVHLEQB-XSSYPUMDSA-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-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:28744 )
2-hydroxy steroid (CHEBI:28744 )
C18 steroids (estrogens) and derivatives (C05301 )
Estrane and derivatives (C05301 )
C18 steroids (estrogens) and derivatives (LMST02010027 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190 - 191 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	3.39	ALOGPS
logP	3.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.89 m³·mol⁻¹	ChemAxon
Polarizability	33.08 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]+	168.132	31661259
DarkChem	[M-H]-	160.765	31661259
AllCCS	[M+H]+	171.833	32859911
AllCCS	[M-H]-	176.136	32859911
DeepCCS	[M-2H]-	213.74	30932474
DeepCCS	[M+Na]+	188.66	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	174.9	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	176.1	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyestradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3	4022.6	Standard polar	33892256
2-Hydroxyestradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3	2798.6	Standard non polar	33892256
2-Hydroxyestradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3	2980.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyestradiol,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O)=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2821.6	Semi standard non polar	33892256
2-Hydroxyestradiol,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC(O)=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O	2810.6	Semi standard non polar	33892256
2-Hydroxyestradiol,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O	2802.1	Semi standard non polar	33892256
2-Hydroxyestradiol,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC(O[Si](C)(C)C)=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2798.1	Semi standard non polar	33892256
2-Hydroxyestradiol,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[C@@H]2O[Si](C)(C)C	2817.7	Semi standard non polar	33892256
2-Hydroxyestradiol,2TMS,isomer #3	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[C@@H]2O	2805.3	Semi standard non polar	33892256
2-Hydroxyestradiol,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[C@@H]2O[Si](C)(C)C	2820.7	Semi standard non polar	33892256
2-Hydroxyestradiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O)=C(O)C=C4[C@H]3CC[C@]12C	3092.6	Semi standard non polar	33892256
2-Hydroxyestradiol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC2	3100.1	Semi standard non polar	33892256
2-Hydroxyestradiol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12	3093.2	Semi standard non polar	33892256
2-Hydroxyestradiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC2	3369.4	Semi standard non polar	33892256
2-Hydroxyestradiol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3339.6	Semi standard non polar	33892256
2-Hydroxyestradiol,2TBDMS,isomer #3	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@@H](O)CC[C@H]3[C@@H]1CC2	3336.0	Semi standard non polar	33892256
2-Hydroxyestradiol,3TBDMS,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@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC2	3535.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adr-2490000000-7e8a9e3990faceb5f6d0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (3 TMS) - 70eV, Positive	splash10-002u-1002900000-79ac7707883246949511	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol GC-MS (TBDMS_3_1) - 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-Hydroxyestradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00ei-2950000000-326e2d3fee4fb8b3ca6c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyestradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-2910000000-553a7988f4c2019ec5d5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Hydroxyestradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0f96-8975000000-eef1fcf44ed6a27f53a9	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Positive-QTOF	splash10-00dr-0190000000-0e1c17e32d9c1e4063eb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Positive-QTOF	splash10-00dr-0790000000-01416dcd9eea3747d3c5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Positive-QTOF	splash10-0006-6970000000-d27a7add654c423ec534	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Negative-QTOF	splash10-000i-0090000000-805faf5743eec20547cb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Negative-QTOF	splash10-000i-0090000000-c39e06f8fdeeb111e97f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Negative-QTOF	splash10-0596-1190000000-36538cb7b1a03d7b2ff7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Positive-QTOF	splash10-000i-0090000000-572916cfebc6538c52d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Positive-QTOF	splash10-01w0-0490000000-7a41b9ec75d4c7c28c73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Positive-QTOF	splash10-004j-3910000000-4dd2fe1697c6e685073e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 10V, Negative-QTOF	splash10-000i-0090000000-843a74fabb1d0eb512a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 20V, Negative-QTOF	splash10-000i-0090000000-40c60966bb1ce4624953	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol 40V, Negative-QTOF	splash10-1009-0090000000-1c821729dedb3f0fecbe	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0016 +/- 0.0014 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8478958	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB07706

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021962

KNApSAcK ID

Not Available

Chemspider ID

216475

KEGG Compound ID

C05301

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hydroxyestradiol

METLIN ID

5327

PubChem Compound

247304

PDB ID

Not Available

ChEBI ID

28744

Food Biomarker Ontology

Not Available

VMH ID

C05301

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kiuru, Paula S.; Wahala, Kristiina. Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol. Steroids (2003), 68(4), 373-375.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. [PubMed:9048584 ]
Takanashi K, Honma T, Kashiwagi T, Honjo H, Yoshizawa I: Detection and measurement of urinary 2-hydroxyestradiol 17-sulfate, a potential placental antioxidant during pregnancy. Clin Chem. 2000 Mar;46(3):373-8. [PubMed:10702524 ]
Elce JS, Bird CE, Chandra J: Water-soluble products of the estrogens. Bile metabolites of 2-hydroxyestradiol-17beta in man. J Clin Endocrinol Metab. 1973 May;36(5):1027-30. [PubMed:4698236 ]
Zhu BT, Conney AH: Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 1998 Jan;19(1):1-27. [PubMed:9472688 ]
Schaeffer JM, Hsueh AJ: 2-Hydroxyestradiol interaction with dopamine receptor binding in rat anterior pituitary. J Biol Chem. 1979 Jul 10;254(13):5606-8. [PubMed:447670 ]

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-Hydroxyestradiol + S-Adenosylmethionine → 2-Methoxyestradiol + S-Adenosylhomocysteine	details

Enzyme Details

2. Protein arginine N-methyltransferase 3

General function:: Involved in protein methyltransferase activity
Specific function:: Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:: PRMT3
Uniprot ID:: O60678
Molecular weight:: 59902.7

Enzyme Details

3. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Showing metabocard for 2-Hydroxyestradiol (HMDB0000338)

MOL for HMDB0000338 (2-Hydroxyestradiol)

3D MOL for HMDB0000338 (2-Hydroxyestradiol)

3D SDF for HMDB0000338 (2-Hydroxyestradiol)

3D-SDF for HMDB0000338 (2-Hydroxyestradiol)

PDB for HMDB0000338 (2-Hydroxyestradiol)

3D PDB for HMDB0000338 (2-Hydroxyestradiol)

SMILES for HMDB0000338 (2-Hydroxyestradiol)

INCHI for HMDB0000338 (2-Hydroxyestradiol)

Structure for HMDB0000338 (2-Hydroxyestradiol)

3D Structure for HMDB0000338 (2-Hydroxyestradiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions