NP-MRD: Showing NP-Card for 2-Hydroxyestradiol (NP0000212)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-09 22:32:54 UTC

NP-MRD ID

NP0000212

Secondary Accession Numbers

None

Natural Product 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>
NP0000212

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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 Mass

288.3814 Da

Monoisotopic Mass

288.17254 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000338

DrugBank ID

DB07706

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

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 ]
Monnet C, Bettsworth F, Stura EA, Le Du MH, Menez R, Derrien L, Zinn-Justin S, Gilquin B, Sibai G, Battail-Poirot N, Jolivet M, Menez A, Arnaud M, Ducancel F, Charbonnier JB: Highly specific anti-estradiol antibodies: structural characterisation and binding diversity. J Mol Biol. 2002 Jan 25;315(4):699-712. doi: 10.1006/jmbi.2001.5284. [PubMed:11812141 ]
Teepker M, Anthes N, Krieg JC, Vedder H: 2-OH-estradiol, an endogenous hormone with neuroprotective functions. J Psychiatr Res. 2003 Nov-Dec;37(6):517-23. doi: 10.1016/s0022-3956(03)00068-2. [PubMed:14563383 ]
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. doi: 10.1210/endo.138.3.4979. [PubMed:9048584 ]
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 ]

Showing NP-Card for 2-Hydroxyestradiol (NP0000212)

MOL for NP0000212 (2-Hydroxyestradiol)

3D MOL for NP0000212 (2-Hydroxyestradiol)

3D SDF for NP0000212 (2-Hydroxyestradiol)

3D-SDF for NP0000212 (2-Hydroxyestradiol)

PDB for NP0000212 (2-Hydroxyestradiol)

3D PDB for NP0000212 (2-Hydroxyestradiol)

SMILES for NP0000212 (2-Hydroxyestradiol)

INCHI for NP0000212 (2-Hydroxyestradiol)

Structure for NP0000212 (2-Hydroxyestradiol)

3D Structure for NP0000212 (2-Hydroxyestradiol)