NP-MRD: Showing NP-Card for 2-Methoxyestrone (NP0000845)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-07-01 14:26:44 UTC

NP-MRD ID

NP0000845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methoxyestrone

Description

2-Methoxyestrone (or 2-ME1) 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-methoxyestrone is considered to be a steroid or steroid derivative. It is a by-product of estrone and 2-hydroxyestrone metabolism and has been detected in all mammals. More specifically, 2-methoxyestrone is an endogenous, naturally occurring methoxylated catechol estrogen and a metabolite of estrone that is formed by catechol O-methyltransferase via the intermediate 2-hydroxyestrone. 2-Methoxyestrone is part of the androgen and estrogen metabolic pathway. The acid ionization constant (pKa) of 2-methoxyestrone has been determined to be 10.81 (PMID: 516114 ). 2-Methoxyestrone can be metabolized to a sulfated derivative (2-methoxyestrone 3-sulfate) via steroid sulfotransferase (EC 2.8.2.15). It can also be glucuronidated to 2-methoxyestrone 3-glucuronide by UDP glucuronosyltransferase (EC 2.4.1.17). Unlike estrone but similarly to 2-hydroxyestrone and 2-methoxyestradiol, 2-methoxyestrone has very low affinity for the estrogen receptor and lacks significant estrogenic activity (PMID: 10865186 ).

Structure

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

      2-Methoxyestrone.mol
  Mrv1652303182019212D          

 25 28  0  0  0  0            999 V2000
   -1.7065   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8659   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6505   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8659    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2775   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -0.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -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
 21 22  1  0  0  0  0
  3 21  1  0  0  0  0
 19 23  1  6  0  0  0
  9 24  1  1  0  0  0
 10 25  1  6  0  0  0
M  END

HMDB0000010
     RDKit          3D
2-Methoxyestrone
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.2991    2.1419   -2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916    1.0028   -1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    0.2802   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490    0.6390   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325   -0.0606    0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -1.1698    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -1.5266    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751   -0.8285   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5157   -1.1931   -0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629   -1.9559    1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -1.0158    2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.4652    0.8196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1536    0.4144    0.0167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4523    0.5918   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404    1.1291   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298    0.3371   -0.3584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9256   -1.0605   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806    0.9766    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6904    1.6665   -0.6715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    0.6426    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593   -0.1961    1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    0.2965    1.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3386    1.9834   -2.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175    2.4306   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    2.9679   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322    1.5110   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744   -2.3913    1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9254   -1.9723    0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507   -2.4843    2.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -2.6794    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3080   -0.2330    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.6530    2.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -1.3544    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.4303    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -0.3163   -1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700    1.3714   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    2.1896   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2807    1.0462   -2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624   -1.8311   -0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -1.1446   -1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863   -1.3151   -1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    0.0847    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2162    1.5770    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8366    0.0392    2.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057   -1.2519    1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735    1.3487    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 12  1  0
 13  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  6
 13 34  1  1
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
M  END

      2-Methoxyestrone.mol
  Mrv1652303182019212D          

 25 28  0  0  0  0            999 V2000
   -1.7065   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8659   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6505   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8659    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2775   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -0.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -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
 21 22  1  0  0  0  0
  3 21  1  0  0  0  0
 19 23  1  6  0  0  0
  9 24  1  1  0  0  0
 10 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000845

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1

> <INCHI_KEY>
WHEUWNKSCXYKBU-QPWUGHHJSA-N

> <FORMULA>
C19H24O3

> <MOLECULAR_WEIGHT>
300.3921

> <EXACT_MASS>
300.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.336101957967095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
4.151357768333334

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957534419499726

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.290800079568816

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8825219384223155

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
85.54559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.49e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000010
     RDKit          3D
2-Methoxyestrone
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.2991    2.1419   -2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916    1.0028   -1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    0.2802   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490    0.6390   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325   -0.0606    0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -1.1698    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -1.5266    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751   -0.8285   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5157   -1.1931   -0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629   -1.9559    1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -1.0158    2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.4652    0.8196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1536    0.4144    0.0167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4523    0.5918   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404    1.1291   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298    0.3371   -0.3584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9256   -1.0605   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806    0.9766    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6904    1.6665   -0.6715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    0.6426    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593   -0.1961    1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    0.2965    1.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3386    1.9834   -2.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175    2.4306   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    2.9679   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322    1.5110   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744   -2.3913    1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9254   -1.9723    0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507   -2.4843    2.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -2.6794    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3080   -0.2330    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.6530    2.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -1.3544    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.4303    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -0.3163   -1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700    1.3714   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    2.1896   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2807    1.0462   -2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624   -1.8311   -0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -1.1446   -1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863   -1.3151   -1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    0.0847    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2162    1.5770    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8366    0.0392    2.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057   -1.2519    1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735    1.3487    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 12  1  0
 13  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  6
 13 34  1  1
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:       2-Methoxyestrone.mol                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.185  -2.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.519  -3.280   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.185  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.852  -0.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.852  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.518  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.816  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.149  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.149  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.483  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.948  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.853   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.948   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.423   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.483   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.483   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.149   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.816   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.816  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.518  -0.970   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.519  -0.200   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.853  -0.970   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       0.816  -1.740   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.149   0.570   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.483  -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   24                                             
CONECT   10    9   11   15   25                                             
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   23                                             
CONECT   20   19    4    6                                                  
CONECT   21   22    3                                                       
CONECT   22   21                                                            
CONECT   23   19                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000010
HETATM    1  C1  UNL     1       4.299   2.142  -2.352  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.692   1.003  -1.611  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.778   0.280  -0.835  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.449   0.639  -0.752  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.532  -0.061   0.007  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.927  -1.170   0.725  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.258  -1.527   0.640  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.175  -0.828  -0.118  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.516  -1.193  -0.200  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.963  -1.956   1.561  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.145  -1.016   2.062  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.784  -0.465   0.820  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.154   0.414   0.017  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.452   0.592  -1.339  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.840   1.129  -1.264  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.730   0.337  -0.358  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.926  -1.060  -0.895  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.981   0.977   0.021  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.690   1.667  -0.672  1.00  0.00           O  
HETATM   20  C17 UNL     1      -4.267   0.643   1.441  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.059  -0.196   1.898  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.013   0.296   1.003  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.339   1.983  -2.890  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.117   2.431  -3.039  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.115   2.968  -1.625  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.132   1.511  -1.315  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.574  -2.391   1.198  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.925  -1.972   0.270  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.451  -2.484   2.377  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.477  -2.679   0.863  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.308  -0.233   2.694  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.873  -1.653   2.567  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.997  -1.354   0.157  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.131   1.430   0.511  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.355  -0.316  -1.975  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.170   1.371  -1.870  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.804   2.190  -0.982  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.281   1.046  -2.301  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.962  -1.831  -0.115  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.904  -1.145  -1.451  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.086  -1.315  -1.574  1.00  0.00           H  
HETATM   42  H20 UNL     1      -5.202   0.085   1.581  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.216   1.577   2.024  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.837   0.039   2.979  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.306  -1.252   1.849  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.774   1.349   1.253  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   13
CONECT    6    7   10
CONECT    7    8    8   27
CONECT    8    9
CONECT    9   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   22   33
CONECT   13   14   34
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   17   18   22
CONECT   17   39   40   41
CONECT   18   19   19   20
CONECT   20   21   42   43
CONECT   21   22   44   45
CONECT   22   46
END

HMDB0000010
     RDKit          3D
2-Methoxyestrone
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.2991    2.1419   -2.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916    1.0028   -1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    0.2802   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490    0.6390   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325   -0.0606    0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -1.1698    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -1.5266    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751   -0.8285   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5157   -1.1931   -0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629   -1.9559    1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -1.0158    2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -0.4652    0.8196 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1536    0.4144    0.0167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4523    0.5918   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404    1.1291   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7298    0.3371   -0.3584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9256   -1.0605   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806    0.9766    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6904    1.6665   -0.6715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    0.6426    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593   -0.1961    1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    0.2965    1.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3386    1.9834   -2.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1175    2.4306   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    2.9679   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322    1.5110   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744   -2.3913    1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9254   -1.9723    0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507   -2.4843    2.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -2.6794    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3080   -0.2330    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.6530    2.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -1.3544    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.4303    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -0.3163   -1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700    1.3714   -1.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    2.1896   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2807    1.0462   -2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624   -1.8311   -0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -1.1446   -1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863   -1.3151   -1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    0.0847    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2162    1.5770    2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8366    0.0392    2.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057   -1.2519    1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735    1.3487    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 12  1  0
 13  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  6
 13 34  1  1
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-(8S,9S,13S,14S)-3-Hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one	HMDB
2-Hydroxyestrone 2-methyl ether	HMDB
2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-ol	HMDB
2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one	HMDB
Methoxy-estrone	HMDB

Chemical Formula

C₁₉H₂₄O₃

Average Mass

300.3921 Da

Monoisotopic Mass

300.17254 Da

IUPAC Name

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

CAS Registry Number

362-08-3

SMILES

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

InChI Identifier

InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1

InChI Key

WHEUWNKSCXYKBU-QPWUGHHJSA-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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 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, 1000 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	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, 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	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, 400 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	¹³C NMR Spectrum (1D, 176 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, 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	¹H NMR Spectrum (1D, 900 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

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
Oxosteroid
17-oxosteroid
Hydroxysteroid
Phenanthrene
Tetralin
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenols (CHEBI:1189 )
alicyclic ketone (CHEBI:1189 )
17-oxo steroid (CHEBI:1189 )
3-hydroxy steroid (CHEBI:1189 )
C18 steroids (estrogens) and derivatives (C05299 )
C18 steroids (estrogens) and derivatives (LMST02010033 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	187.0 - 189.5 °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	0.0075 g/L	ALOGPS
logP	3.5	ALOGPS
logP	4.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.55 m³·mol⁻¹	ChemAxon
Polarizability	34.34 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

HMDB0000010

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021868

KNApSAcK ID

Not Available

Chemspider ID

389515

KEGG Compound ID

C05299

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Methoxyestrone

METLIN ID

2578

PubChem Compound

440624

PDB ID

Not Available

ChEBI ID

1189

Good Scents ID

Not Available

References

General References

Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
Longcope C, Flood C, Femino A, Williams KI: Metabolism of 2-methoxyestrone in normal men. J Clin Endocrinol Metab. 1983 Aug;57(2):277-82. [PubMed:6863476 ]
Ball P, Reu G, Schwab J, Knuppen R: Radioimmunoassay of 2-hydroxyesterone and 2-methoxyestrone in human urine. Steroids. 1979 May;33(5):563-76. [PubMed:462497 ]
Lewis KM, Archer RD: pKa values of estrone, 17 beta-estradiol and 2-methoxyestrone. Steroids. 1979 Nov;34(5):485-99. [PubMed:516114 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK: Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women. J Soc Gynecol Investig. 2000 May-Jun;7(3):175-83. doi: 10.1016/s1071-5576(00)00049-6. [PubMed:10865186 ]
(). S. Kraychy, T. F. Gallagher. 2-Methoxyestrone, A Metabolite of Estradiol-17β in the Human. J. Am. Chem. Soc., 1957, 79 (3), pp 754–754. .
(). Miyazaki M, Fishman J. Isomeric aryl monsulfates of estrogen catechols. J Org Chem. 1968 Feb;33(2):662-4. .
(). Shimada, K. et al., J. Chromatogr., 1979, 178, 350, (HPLC). .
(). Gelbke, H.P. et al., Steroids, 1973, 21, 205, (synthesis, PMR). .
(). Douglas GH, Walk CR, Smith H. Totally synthetic steroid hormones. V. (+ -)-2,3-Dimethoxyestra-1,3,5(10)-trien-17-beta-ol and some congeners. J Med Chem. 1966 Jan;9(1):27-9.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for 2-Methoxyestrone (NP0000845)

MOL for NP0000845 (2-Methoxyestrone)

3D MOL for NP0000845 (2-Methoxyestrone)

3D SDF for NP0000845 (2-Methoxyestrone)

3D-SDF for NP0000845 (2-Methoxyestrone)

PDB for NP0000845 (2-Methoxyestrone)

3D PDB for NP0000845 (2-Methoxyestrone)

SMILES for NP0000845 (2-Methoxyestrone)

INCHI for NP0000845 (2-Methoxyestrone)

Structure for NP0000845 (2-Methoxyestrone)

3D Structure for NP0000845 (2-Methoxyestrone)