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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 02:49:01 UTC

HMDB ID

HMDB0000405

Secondary Accession Numbers

HMDB00405

Metabolite Identification

Common Name

2-Methoxyestradiol

Description

2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumours need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. 2ME2 also acts as a vasodilator.

Structure

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

2-Methoxyestradiol.mol
  Mrv1652305261923542D          

 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  1  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
    2.9054    1.7572    0.0000 O   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  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
  6 19  2  0  0  0  0
 20 21  1  0  0  0  0
  3 20  1  0  0  0  0
 18 22  1  6  0  0  0
  9 23  1  1  0  0  0
 10 24  1  6  0  0  0
 13 25  1  1  0  0  0
M  END

HMDB0000405
     RDKit          3D
2-Methoxyestradiol
 48 51  0  0  0  0  0  0  0  0999 V2000
   -5.0917    2.0585    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1345    0.7296    0.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659   -0.0250    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    0.4868    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080   -0.2839   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -1.5938   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232   -2.1082   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -1.3327    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5919   -1.8491    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -2.4891   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -1.6152   -1.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089   -0.6826   -0.5493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3821    0.3244   -0.1759 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0602    0.9589    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.6888    0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.7554    0.3872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8642   -0.2646    1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    1.4435   -0.1755 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5295    1.8633    0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119    0.3891   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0702   -0.5683   -1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865    0.1180   -0.9016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8118    2.1825    2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    2.4677    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738    2.7179    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    1.5190    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596   -3.1371   -0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7358   -2.8185   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296   -2.9762   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -3.2309   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2515   -1.0522   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433   -2.2627   -1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926   -1.2716    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    1.1273   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735    1.6319    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875    0.1174    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    2.0258    1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    2.5551    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -0.0934    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946   -0.2322    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272   -1.3022    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    2.3093   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    2.2387    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566   -0.1264   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383    0.9184   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.6838   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2599   -1.5788   -1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961    0.9509   -1.5608 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  1
 16 18  1  0
 18 19  1  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  1
 13 34  1  6
 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
 18 42  1  6
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  6
M  END

2-Methoxyestradiol.mol
  Mrv1652305261923542D          

 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  1  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
    2.9054    1.7572    0.0000 O   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  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
  6 19  2  0  0  0  0
 20 21  1  0  0  0  0
  3 20  1  0  0  0  0
 18 22  1  6  0  0  0
  9 23  1  1  0  0  0
 10 24  1  6  0  0  0
 13 25  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000405

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/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/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1

> <INCHI_KEY>
CQOQDQWUFQDJMK-SSTWWWIQSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.20085771933594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.587830062666667

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37769223665156

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.29090278168336

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839539517980656

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
86.36789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000405
     RDKit          3D
2-Methoxyestradiol
 48 51  0  0  0  0  0  0  0  0999 V2000
   -5.0917    2.0585    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1345    0.7296    0.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659   -0.0250    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    0.4868    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080   -0.2839   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -1.5938   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232   -2.1082   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -1.3327    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5919   -1.8491    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -2.4891   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -1.6152   -1.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089   -0.6826   -0.5493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3821    0.3244   -0.1759 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0602    0.9589    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.6888    0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.7554    0.3872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8642   -0.2646    1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    1.4435   -0.1755 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5295    1.8633    0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119    0.3891   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0702   -0.5683   -1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865    0.1180   -0.9016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8118    2.1825    2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    2.4677    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738    2.7179    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    1.5190    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596   -3.1371   -0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7358   -2.8185   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296   -2.9762   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -3.2309   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2515   -1.0522   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433   -2.2627   -1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926   -1.2716    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    1.1273   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735    1.6319    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875    0.1174    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    2.0258    1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    2.5551    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -0.0934    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946   -0.2322    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272   -1.3022    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    2.3093   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    2.2387    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566   -0.1264   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383    0.9184   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.6838   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2599   -1.5788   -1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961    0.9509   -1.5608 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  1
 16 18  1  0
 18 19  1  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  1
 13 34  1  6
 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
 18 42  1  6
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  6
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Methoxyestradiol.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         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  C   UNK     0       3.483   1.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.483   2.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.149   2.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.816   1.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.816  -0.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.518  -0.970   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.519  -0.200   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.853  -0.970   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.816  -1.740   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.149   0.570   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.483  -1.740   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       5.423   3.280   0.000  0.00  0.00           O+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4   20                                                  
CONECT    4    3   19                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18   23                                             
CONECT   10    9   11   14   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   10   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    9   19   22                                             
CONECT   19   18    4    6                                                  
CONECT   20   21    3                                                       
CONECT   21   20                                                            
CONECT   22   18                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000405
HETATM    1  C1  UNL     1      -5.092   2.058   1.197  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.135   0.730   0.791  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.066  -0.025   0.368  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.768   0.487   0.297  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.708  -0.284  -0.130  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.944  -1.594  -0.496  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.223  -2.108  -0.429  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.304  -1.333   0.003  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.592  -1.849   0.071  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.839  -2.489  -0.970  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.217  -1.615  -1.617  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.709  -0.683  -0.549  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.382   0.324  -0.176  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.060   0.959   1.101  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.361   1.689   0.896  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.429   0.755   0.387  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.864  -0.265   1.381  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.624   1.444  -0.175  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.529   1.863   0.787  1.00  0.00           O  
HETATM   20  C17 UNL     1       4.212   0.389  -1.092  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.070  -0.568  -1.429  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.887   0.118  -0.902  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.812   2.182   2.273  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.140   2.468   1.136  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.474   2.718   0.572  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.659   1.519   0.599  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.460  -3.137  -0.707  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.736  -2.819  -0.205  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.430  -2.976  -0.063  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.223  -3.231  -1.695  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.251  -1.052  -2.452  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.043  -2.263  -1.927  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.893  -1.272   0.373  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.346   1.127  -0.968  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.673   1.632   1.562  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.288   0.117   1.820  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.694   2.026   1.918  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.279   2.555   0.229  1.00  0.00           H  
HETATM   39  H17 UNL     1       3.938  -0.093   1.687  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.295  -0.232   2.336  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.827  -1.302   1.020  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.255   2.309  -0.786  1.00  0.00           H  
HETATM   43  H21 UNL     1       5.315   2.239   0.290  1.00  0.00           H  
HETATM   44  H22 UNL     1       5.057  -0.126  -0.606  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.538   0.918  -2.030  1.00  0.00           H  
HETATM   46  H24 UNL     1       3.018  -0.684  -2.532  1.00  0.00           H  
HETATM   47  H25 UNL     1       3.260  -1.579  -1.022  1.00  0.00           H  
HETATM   48  H26 UNL     1       1.596   0.951  -1.561  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   20   42
CONECT   19   43
CONECT   20   21   44   45
CONECT   21   22   46   47
CONECT   22   48
END

HMDB0000405
     RDKit          3D
2-Methoxyestradiol
 48 51  0  0  0  0  0  0  0  0999 V2000
   -5.0917    2.0585    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1345    0.7296    0.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659   -0.0250    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683    0.4868    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080   -0.2839   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -1.5938   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232   -2.1082   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -1.3327    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5919   -1.8491    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -2.4891   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -1.6152   -1.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089   -0.6826   -0.5493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3821    0.3244   -0.1759 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0602    0.9589    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.6888    0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.7554    0.3872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8642   -0.2646    1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    1.4435   -0.1755 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5295    1.8633    0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119    0.3891   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0702   -0.5683   -1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865    0.1180   -0.9016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8118    2.1825    2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    2.4677    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738    2.7179    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6594    1.5190    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596   -3.1371   -0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7358   -2.8185   -0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4296   -2.9762   -0.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -3.2309   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2515   -1.0522   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433   -2.2627   -1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926   -1.2716    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    1.1273   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735    1.6319    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875    0.1174    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    2.0258    1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    2.5551    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -0.0934    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946   -0.2322    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272   -1.3022    1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552    2.3093   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    2.2387    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566   -0.1264   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383    0.9184   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.6838   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2599   -1.5788   -1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961    0.9509   -1.5608 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  1
 16 18  1  0
 18 19  1  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  1
 13 34  1  6
 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
 18 42  1  6
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,5(10)-ESTRATRIEN-2,3,17-BETA-triol 2-methyl ether	ChEBI
2-Hydroxyestradol 2-methyl ether	ChEBI
2-Methoxyestradiol-17beta	ChEBI
Panzem	ChEBI
1,3,5(10)-ESTRATRIEN-2,3,17-b-triol 2-methyl ether	Generator
1,3,5(10)-ESTRATRIEN-2,3,17-β-triol 2-methyl ether	Generator
2-Methoxyestradiol-17b	Generator
2-Methoxyestradiol-17β	Generator
2-(Methyl-11C)methoxyestradiol	HMDB
2-Methoxyestradiol, (17alpha)-isomer	HMDB
2-Methoxyoestradiol	HMDB
2-Methoxyestradiol-17 beta	HMDB
2ME2	HMDB
(17Β)-2-methoxyestra-1,3,5(10)-triene-3,17-diol	HMDB
(17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol	HMDB
2-Hydroxyestradiol 2-methyl ether	HMDB
2-Methoxy-e2	HMDB
2-Methoxyestra-1,3,5(10)-triene-3,17β-diol	HMDB
2-Methoxyestra-1,3,5(10)-triene-3,17beta-diol	HMDB
2 Methoxyoestradiol	HMDB
(17 beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol	HMDB
2 Methoxyestradiol 17 beta	HMDB
2 Methoxyestradiol	HMDB
2-Methoxyestradiol	HMDB, ChEBI

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.4079

Monoisotopic Molecular Weight

302.188194698

IUPAC Name

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

Traditional Name

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

CAS Registry Number

362-07-2

SMILES

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

InChI Identifier

InChI=1S/C19H26O3/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/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1

InChI Key

CQOQDQWUFQDJMK-SSTWWWIQSA-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
17-hydroxysteroid
Hydroxysteroid
Phenanthrene
Tetralin
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Cyclic alcohol
Secondary alcohol
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:28955 )
3-hydroxy steroid (CHEBI:28955 )
C18 steroids (estrogens) and derivatives (C05302 )
Estrane and derivatives (C05302 )
C18 steroids (estrogens) and derivatives (LMST02010035 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189 - 190 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0097 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.59	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.37 m³·mol⁻¹	ChemAxon
Polarizability	35.2 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]+	172.903	31661259
DarkChem	[M-H]-	173.209	31661259
AllCCS	[M+H]+	175.532	32859911
AllCCS	[M-H]-	180.228	32859911
DeepCCS	[M-2H]-	215.934	30932474
DeepCCS	[M+Na]+	190.925	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.3	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	180.2	32859911
AllCCS	[M+HCOO]-	180.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxyestradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3	3790.8	Standard polar	33892256
2-Methoxyestradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3	2605.1	Standard non polar	33892256
2-Methoxyestradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3	2814.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxyestradiol,1TMS,isomer #1	COC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]12	2793.8	Semi standard non polar	33892256
2-Methoxyestradiol,1TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12	2781.3	Semi standard non polar	33892256
2-Methoxyestradiol,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]12	2778.2	Semi standard non polar	33892256
2-Methoxyestradiol,1TBDMS,isomer #1	COC1=CC2=C(C=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3082.6	Semi standard non polar	33892256
2-Methoxyestradiol,1TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12	3072.2	Semi standard non polar	33892256
2-Methoxyestradiol,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@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3296.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methoxyestradiol GC-MS (2 TMS)	splash10-016s-2792200000-4c8c5cfcb17a537e5130	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methoxyestradiol GC-MS (Non-derivatized)	splash10-016s-2792200000-4c8c5cfcb17a537e5130	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-1190000000-c0b6f1d0f5e462b22c79	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (2 TMS) - 70eV, Positive	splash10-00lr-2114900000-32b6a1587678bf94533f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxyestradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methoxyestradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-51addcf0be873acf4568	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methoxyestradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-9189876ead18b5520cfc	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methoxyestradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ue9-0900000000-c60cd007c37d58b43c6f	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 10V, Positive-QTOF	splash10-0f79-0197000000-e6452081e4d95484a78e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 20V, Positive-QTOF	splash10-0f79-0592000000-f334c69fd08d4a298998	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 40V, Positive-QTOF	splash10-052u-3690000000-d1b1dc06b52f7fe1f05c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 10V, Negative-QTOF	splash10-0udi-0019000000-2e5aedfaa3bc522112af	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 20V, Negative-QTOF	splash10-0udi-0069000000-2106698fbc9b5342a9b1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 40V, Negative-QTOF	splash10-0a70-0090000000-299f520e49dfbd52ed63	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 10V, Negative-QTOF	splash10-0udi-0009000000-4360bacaf95498925fe5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 20V, Negative-QTOF	splash10-0udi-0019000000-b5cab14cef0400c3f7b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 40V, Negative-QTOF	splash10-014i-0090000000-98926d2ec85f54a46632	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 10V, Positive-QTOF	splash10-0udi-0029000000-1d8e847a4bc26e5c1212	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 20V, Positive-QTOF	splash10-0fbi-0594000000-53e59c7ba30eb8c1eb1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxyestradiol 40V, Positive-QTOF	splash10-056v-3930000000-32bdd6b4eab8d995c641	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.01000 +/- 0.00066 uM	Adult (>18 years old)	Both	Normal	15818726	details
Urine	Detected and Quantified	0.004 +/- 0.0009 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	12553956	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0010 (0.0033-0.0210) uM	Adult (>18 years old)	Female	Ovarian cancer	15818726	details

Associated Disorders and Diseases

Disease References

Ovarian cancer
Lakhani NJ, Lepper ER, Sparreboom A, Dahut WL, Venitz J, Figg WD: Determination of 2-methoxyestradiol in human plasma, using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(9):1176-82. [PubMed:15818726 ]

Associated OMIM IDs

167000 (Ovarian cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022021

KNApSAcK ID

Not Available

Chemspider ID

59788

KEGG Compound ID

C05302

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Methoxyestradiol

METLIN ID

5394

PubChem Compound

66414

PDB ID

Not Available

ChEBI ID

28955

Food Biomarker Ontology

Not Available

VMH ID

C05302

MarkerDB ID

MDB00000157

Good Scents ID

Not Available

References

Synthesis Reference

Zhang, Beina; Wang, Hongbo; Zhang, Qian; Chen, Ying; Xia, Peng. An improved process for synthesis of 2-methoxyestradiol. Fudan Xuebao, Yixueban (2003), 30(5), 494-495.

Material Safety Data Sheet (MSDS)

Not Available

General References

Schumacher G, Neuhaus P: The physiological estrogen metabolite 2-methoxyestradiol reduces tumor growth and induces apoptosis in human solid tumors. J Cancer Res Clin Oncol. 2001 Jul;127(7):405-10. [PubMed:11469676 ]
Kumar AP, Garcia GE, Slaga TJ: 2-methoxyestradiol blocks cell-cycle progression at G(2)/M phase and inhibits growth of human prostate cancer cells. Mol Carcinog. 2001 Jul;31(3):111-24. [PubMed:11479920 ]
Lakhani NJ, Lepper ER, Sparreboom A, Dahut WL, Venitz J, Figg WD: Determination of 2-methoxyestradiol in human plasma, using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(9):1176-82. [PubMed:15818726 ]
Bu S, Blaukat A, Fu X, Heldin NE, Landstrom M: Mechanisms for 2-methoxyestradiol-induced apoptosis of prostate cancer cells. FEBS Lett. 2002 Nov 6;531(2):141-51. [PubMed:12417302 ]
Pico C, Puigserver P, Oliver P, Palou A: 2-Methoxyestradiol, an endogenous metabolite of 17beta-estradiol, inhibits adipocyte proliferation. Mol Cell Biochem. 1998 Dec;189(1-2):1-7. [PubMed:9879647 ]
Lakhani NJ, Sparreboom A, Dahut WL, Venitz J, Figg WD: Determination of the antiangiogenesis agent 2-methoxyestradiol in human plasma by liquid chromatography with ultraviolet detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jul 5;806(2):289-93. [PubMed:15171941 ]

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-Hydroxyestradiol + S-Adenosylmethionine → 2-Methoxyestradiol + 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. Protein arginine N-methyltransferase 3

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

Enzyme Details

5. 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. 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-Methoxyestradiol + Uridine diphosphate glucuronic acid → 2-Methoxy-estradiol-17b 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-Methoxyestradiol (HMDB0000405)

MOL for HMDB0000405 (2-Methoxyestradiol)

3D MOL for HMDB0000405 (2-Methoxyestradiol)

3D SDF for HMDB0000405 (2-Methoxyestradiol)

3D-SDF for HMDB0000405 (2-Methoxyestradiol)

PDB for HMDB0000405 (2-Methoxyestradiol)

3D PDB for HMDB0000405 (2-Methoxyestradiol)

SMILES for HMDB0000405 (2-Methoxyestradiol)

INCHI for HMDB0000405 (2-Methoxyestradiol)

Structure for HMDB0000405 (2-Methoxyestradiol)

3D Structure for HMDB0000405 (2-Methoxyestradiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions