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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (23) Show 23 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:58 UTC

HMDB ID

HMDB0000010

Secondary Accession Numbers

HMDB00010
HMDB0004990
HMDB0004991
HMDB04990
HMDB04991

Metabolite 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>
HMDB0000010

> <DATABASE_NAME>
hmdb

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

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 Molecular Weight

300.3921

Monoisotopic Molecular Weight

300.172544634

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

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 )

Ontology

Physiological effect

Health effect

Endocrine system disorder

Pituitary, hypothalamus, or pineal disorder

Prolactinoma (HMDB: HMDB0000010)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000010)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 9812172)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000010)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000010)

Source

Endogenous

Endogenous (HMDB: HMDB0000010)

Animal

Animal (HMDB: HMDB0000010)

Exogenous

Food

Food (HMDB: HMDB0000010)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000010)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000010)

Molecular messenger

Hormone (HMDB: HMDB0000010)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000010)

Pharmaceutical industry

Biomarker

Prolactinoma (MarkerDB: MDB00000004)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	184.553	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001854
[M+H]+	Not Available	174.466	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001854

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.972	31661259
DarkChem	[M-H]-	172.441	31661259
AllCCS	[M+H]+	173.507	32859911
AllCCS	[M-H]-	180.081	32859911
DeepCCS	[M-2H]-	213.623	30932474
DeepCCS	[M+Na]+	188.759	30932474
AllCCS	[M+H]+	173.5	32859911
AllCCS	[M+H-H2O]+	170.4	32859911
AllCCS	[M+NH4]+	176.4	32859911
AllCCS	[M+Na]+	177.3	32859911
AllCCS	[M-H]-	180.1	32859911
AllCCS	[M+Na-2H]-	179.9	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.74 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5162 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2365.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	663.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	621.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1335.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	479.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1376.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	439.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	281.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	301.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxyestrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3	3613.2	Standard polar	33892256
2-Methoxyestrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3	2579.0	Standard non polar	33892256
2-Methoxyestrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3	2787.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxyestrone,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12	2817.4	Semi standard non polar	33892256
2-Methoxyestrone,1TMS,isomer #2	COC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C)=CC[C@@H]12	2756.0	Semi standard non polar	33892256
2-Methoxyestrone,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C)=CC[C@@H]12	2734.4	Semi standard non polar	33892256
2-Methoxyestrone,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C)=CC[C@@H]12	2657.1	Standard non polar	33892256
2-Methoxyestrone,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C)=CC[C@@H]12	3077.2	Standard polar	33892256
2-Methoxyestrone,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12	3089.8	Semi standard non polar	33892256
2-Methoxyestrone,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]12	3023.2	Semi standard non polar	33892256
2-Methoxyestrone,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]12	3197.4	Semi standard non polar	33892256
2-Methoxyestrone,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]12	3055.3	Standard non polar	33892256
2-Methoxyestrone,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]12	3326.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Estrone Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.005 (0.004-0.006) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9812172	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.025 (0.02-0.03) umol/mmol creatinine	Adult (>18 years old)	Both	Prolactinoma	9812172	details

Associated Disorders and Diseases

Disease References

Prolactinoma
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 ]

Associated OMIM IDs

600634 (Prolactinoma)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

C05299

MarkerDB ID

MDB00000004

Good Scents ID

Not Available

References

Synthesis Reference

Stoelwinder, Johannes; Moers, Nicolaas Elisabeth Cornelis. Process for the preparation 2-substituted derivatives of estrone and estradiol.PCT Int. Appl. (2006), 40 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

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.

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

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

Reactions

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

Enzyme Details

2. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

3. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Showing metabocard for 2-Methoxyestrone (HMDB0000010)

MOL for HMDB0000010 (2-Methoxyestrone)

3D MOL for HMDB0000010 (2-Methoxyestrone)

3D SDF for HMDB0000010 (2-Methoxyestrone)

3D-SDF for HMDB0000010 (2-Methoxyestrone)

PDB for HMDB0000010 (2-Methoxyestrone)

3D PDB for HMDB0000010 (2-Methoxyestrone)

SMILES for HMDB0000010 (2-Methoxyestrone)

INCHI for HMDB0000010 (2-Methoxyestrone)

Structure for HMDB0000010 (2-Methoxyestrone)

3D Structure for HMDB0000010 (2-Methoxyestrone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

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