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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

HMDB0000380

Secondary Accession Numbers

HMDB00380

Metabolite Identification

Common Name

2-Hydroxyestradiol-3-methyl ether

Description

2-Hydroxyestradiol-3-methylether is a methoxylated derivative of 2-hydroxyestradiol. 2-hydroxy estrogen metabolites can be converted to anticarcinogenic methoxylated metabolites (2-methoxyestrone and 2-methoxyestradiol, 2-hydroxyestrone and 2-hydroxyestradiol 3-methyl ether) by catechol O-methyltransferase (PMID: 11172156 ). 2-hydroxyestradiol 3-methyl ether has been found in the urine of pregnant women (along with other 2-hydroxyestrogen ethers) although the amounts are generally small (less than 5 ug/24 hours). (PMID: 966757 ).

Structure

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


  Mrv0541 02231218292D          

 25 28  0  0  1  0            999 V2000
   16.8140  -11.9263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8346  -12.7327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1466  -13.1538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4380  -12.7685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5707  -11.6611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1054  -11.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6039  -12.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4172  -11.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0579  -12.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1810  -13.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7146  -13.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4678  -14.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7297  -14.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9555  -12.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9867  -14.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2021  -13.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2177  -14.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8694  -11.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6528  -10.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4923  -13.6359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1466  -12.2557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8666  -13.4441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0669  -12.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1061  -14.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9660  -14.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
  1 18  1  1  0  0  0
  5 19  1  1  0  0  0
  4 20  1  6  0  0  0
  3 21  1  1  0  0  0
  2 22  1  6  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 24  1  0  0  0  0
M  END

HMDB0000380
     RDKit          3D
2-Hydroxyestradiol-3-methyl ether
 48 51  0  0  0  0  0  0  0  0999 V2000
    6.3322   -0.7963    0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4844   -1.2026   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -0.8347   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953   -0.0267    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689    0.3119    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.1421   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -0.9588   -1.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253   -1.2865   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -2.0980   -2.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.2912   -0.5560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6827   -0.3097   -1.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    0.2732   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    0.1395   -0.3539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9770   -1.2949    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9707    0.9355   -0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0891    0.3306   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.0271    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7142    0.8259    1.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    0.8324    0.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5796    0.0629    0.7928 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2858    0.4811    1.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    1.1784    1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020    0.2973    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433   -1.3519    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3946   -0.8699    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.3551    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946   -1.3027   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5670   -2.4644   -3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.3975   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801   -0.0307   -2.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.4097   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -0.2963   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582    1.3223   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0103   -1.5835   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -1.4844    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2676   -2.0071   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    1.9319   -0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4302    0.8922   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768    0.2339    1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    2.0459    1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.0620    2.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212    1.6982    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447    1.8536    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -1.0512    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    1.0960    2.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5822   -0.4259    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805    1.2882    2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    2.1881    1.1223 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  1
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 20 10  1  0
 22  5  1  0
 19 13  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  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  6
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 20 44  1  1
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
M  END


  Mrv0541 02231218292D          

 25 28  0  0  1  0            999 V2000
   16.8140  -11.9263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8346  -12.7327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1466  -13.1538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4380  -12.7685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5707  -11.6611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1054  -11.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6039  -12.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4172  -11.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0579  -12.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1810  -13.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7146  -13.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4678  -14.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7297  -14.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9555  -12.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9867  -14.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2021  -13.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2177  -14.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8694  -11.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6528  -10.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4923  -13.6359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1466  -12.2557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8666  -13.4441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0669  -12.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1061  -14.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9660  -14.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
  1 18  1  1  0  0  0
  5 19  1  1  0  0  0
  4 20  1  6  0  0  0
  3 21  1  1  0  0  0
  2 22  1  6  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000380

> <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(OC)C(O)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-17(22-2)16(20)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>
MMKYSUOJWFKECQ-SSTWWWIQSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.22058565859514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.587830062666667

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37769223665156

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.323122768321674

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839540460266336

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
86.36789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000380
     RDKit          3D
2-Hydroxyestradiol-3-methyl ether
 48 51  0  0  0  0  0  0  0  0999 V2000
    6.3322   -0.7963    0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4844   -1.2026   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -0.8347   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953   -0.0267    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689    0.3119    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.1421   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -0.9588   -1.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253   -1.2865   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -2.0980   -2.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.2912   -0.5560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6827   -0.3097   -1.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    0.2732   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    0.1395   -0.3539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9770   -1.2949    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9707    0.9355   -0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0891    0.3306   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.0271    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7142    0.8259    1.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    0.8324    0.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5796    0.0629    0.7928 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2858    0.4811    1.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    1.1784    1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020    0.2973    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433   -1.3519    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3946   -0.8699    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.3551    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946   -1.3027   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5670   -2.4644   -3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.3975   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801   -0.0307   -2.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.4097   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -0.2963   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582    1.3223   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0103   -1.5835   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -1.4844    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2676   -2.0071   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    1.9319   -0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4302    0.8922   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768    0.2339    1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    2.0459    1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.0620    2.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212    1.6982    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447    1.8536    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -1.0512    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    1.0960    2.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5822   -0.4259    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805    1.2882    2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    2.1881    1.1223 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  1
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 20 10  1  0
 22  5  1  0
 19 13  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  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  6
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 20 44  1  1
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      31.386 -22.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.425 -23.768   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.140 -24.554   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.818 -23.835   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.799 -21.767   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.063 -21.543   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.861 -24.190   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.779 -22.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.708 -22.956   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.205 -26.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.467 -24.632   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.873 -26.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.495 -26.201   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.050 -23.819   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.109 -27.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.644 -24.650   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.673 -26.284   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.490 -20.980   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      32.952 -20.235   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0      28.919 -25.454   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      30.140 -22.877   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      31.484 -25.096   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      22.525 -23.466   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      22.598 -27.543   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      20.470 -26.375   0.000  0.00  0.00           C+0
CONECT    1    2    5    6   18                                             
CONECT    2    1    3    7   22                                             
CONECT    3    2    4   10   21                                             
CONECT    4    3    8   11   20                                             
CONECT    5    1    9   19                                                  
CONECT    6    1    8                                                       
CONECT    7    2    9                                                       
CONECT    8    4    6                                                       
CONECT    9    5    7                                                       
CONECT   10    3   12                                                       
CONECT   11    4   13   14                                                  
CONECT   12   10   13                                                       
CONECT   13   11   12   15                                                  
CONECT   14   11   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17   23                                                  
CONECT   17   15   16   24                                                  
CONECT   18    1                                                            
CONECT   19    5                                                            
CONECT   20    4                                                            
CONECT   21    3                                                            
CONECT   22    2                                                            
CONECT   23   16                                                            
CONECT   24   17   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000380
HETATM    1  C1  UNL     1       6.332  -0.796   0.912  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.484  -1.203  -0.144  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.165  -0.835  -0.245  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.595  -0.027   0.714  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.269   0.312   0.564  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.519  -0.142  -0.516  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.097  -0.959  -1.483  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.425  -1.287  -1.317  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.050  -2.098  -2.253  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.120   0.291  -0.556  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.683  -0.310  -1.665  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.059   0.273  -1.684  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.722   0.140  -0.354  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.977  -1.295   0.008  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.971   0.935  -0.191  1.00  0.00           C  
HETATM   16  O3  UNL     1      -5.089   0.331  -0.751  1.00  0.00           O  
HETATM   17  C14 UNL     1      -4.096   1.027   1.328  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.714   0.826   1.886  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.843   0.832   0.698  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.580   0.063   0.793  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.286   0.481   1.936  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.548   1.178   1.536  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.102   0.297   1.076  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.043  -1.352   1.826  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.395  -0.870   0.655  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.125   0.355   1.571  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.495  -1.303  -2.319  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.567  -2.464  -3.063  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.114   1.398  -0.697  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.180  -0.031  -2.623  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.715  -1.410  -1.616  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.662  -0.296  -2.442  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.058   1.322  -2.026  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.010  -1.583  -0.344  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.983  -1.484   1.099  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.268  -2.007  -0.436  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.814   1.932  -0.652  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.430   0.892  -1.493  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.777   0.234   1.660  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.454   2.046   1.627  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.619  -0.062   2.522  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.421   1.698   2.540  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.645   1.854   0.326  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.762  -1.051   0.820  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.317   1.096   2.650  1.00  0.00           H  
HETATM   46  H24 UNL     1       0.582  -0.426   2.533  1.00  0.00           H  
HETATM   47  H25 UNL     1       2.180   1.288   2.436  1.00  0.00           H  
HETATM   48  H26 UNL     1       1.355   2.188   1.122  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   22
CONECT    6    7   10
CONECT    7    8    8   27
CONECT    8    9
CONECT    9   28
CONECT   10   11   20   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   15   19
CONECT   14   34   35   36
CONECT   15   16   17   37
CONECT   16   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   20   43
CONECT   20   21   44
CONECT   21   22   45   46
CONECT   22   47   48
END

HMDB0000380
     RDKit          3D
2-Hydroxyestradiol-3-methyl ether
 48 51  0  0  0  0  0  0  0  0999 V2000
    6.3322   -0.7963    0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4844   -1.2026   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -0.8347   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953   -0.0267    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689    0.3119    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.1421   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -0.9588   -1.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253   -1.2865   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0499   -2.0980   -2.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    0.2912   -0.5560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6827   -0.3097   -1.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    0.2732   -1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7216    0.1395   -0.3539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9770   -1.2949    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9707    0.9355   -0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0891    0.3306   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.0271    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7142    0.8259    1.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    0.8324    0.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5796    0.0629    0.7928 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2858    0.4811    1.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    1.1784    1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020    0.2973    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433   -1.3519    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3946   -0.8699    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.3551    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946   -1.3027   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5670   -2.4644   -3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    1.3975   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801   -0.0307   -2.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.4097   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -0.2963   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582    1.3223   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0103   -1.5835   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -1.4844    1.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2676   -2.0071   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    1.9319   -0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4302    0.8922   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768    0.2339    1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    2.0459    1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.0620    2.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212    1.6982    2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447    1.8536    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -1.0512    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    1.0960    2.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5822   -0.4259    2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805    1.2882    2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    2.1881    1.1223 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  1
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 20 10  1  0
 22  5  1  0
 19 13  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  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  6
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 20 44  1  1
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(17beta)-3-Methoxyestra-1(10),2,4-triene-2,17-diol	ChEBI
2,3,17beta-Trihydroxy-1,3,5[10]-estratriene 2-methyl ether	ChEBI
2-Hydroxy-3-methoxy-17beta-estradiol	ChEBI
3,17beta-Dihydroxy-2-methoxy-1,3,5[10]-estratriene	ChEBI
3-Methoxy-1,3,5[10]-estratriene-2,17beta-diol	ChEBI
3-O-Methyl-2-hydroxyestradiol	ChEBI
(17b)-3-Methoxyestra-1(10),2,4-triene-2,17-diol	Generator
(17Β)-3-methoxyestra-1(10),2,4-triene-2,17-diol	Generator
2,3,17b-Trihydroxy-1,3,5[10]-estratriene 2-methyl ether	Generator
2,3,17Β-trihydroxy-1,3,5[10]-estratriene 2-methyl ether	Generator
2-Hydroxy-3-methoxy-17b-estradiol	Generator
2-Hydroxy-3-methoxy-17β-estradiol	Generator
3,17b-Dihydroxy-2-methoxy-1,3,5[10]-estratriene	Generator
3,17Β-dihydroxy-2-methoxy-1,3,5[10]-estratriene	Generator
3-Methoxy-1,3,5[10]-estratriene-2,17b-diol	Generator
3-Methoxy-1,3,5[10]-estratriene-2,17β-diol	Generator
2-OH-3-MeOE2	MeSH
2-Hydroxy-3-methoxyestradiol	MeSH
(17b)-3-Methoxy-estra-1,3,5(10)-triene-2,17-diol	HMDB
2-Hydroxy-17b-estradiol 3-methyl ether	HMDB
2-Hydroxyestradiol 3-methyl ether	HMDB
2-Hydroxyestradiol-3-methylether2-hydroxy-3-methoxy-17beta-estradiol	HMDB
2H3MeOE2	HMDB
3-Methoxy-estra-1,3,5(10)-triene-2,17b-diol	HMDB

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.4079

Monoisotopic Molecular Weight

302.188194698

IUPAC Name

(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol

Traditional Name

(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol

CAS Registry Number

5976-65-8

SMILES

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

InChI Identifier

InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-17(22-2)16(20)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

MMKYSUOJWFKECQ-SSTWWWIQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

C18 steroids (estrogens) and derivatives (LMST02010051 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000380)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 9812172)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000380)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000380)

Source

Endogenous

Endogenous (HMDB: HMDB0000380)

Animal

Animal (HMDB: HMDB0000380)

Exogenous

Food

Food (HMDB: HMDB0000380)

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: HMDB0000380)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000380)

Molecular messenger

Hormone (HMDB: HMDB0000380)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000380)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.0099 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.59	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.32	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	35.22 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]+	172.715	31661259
DarkChem	[M-H]-	171.027	31661259
AllCCS	[M+H]+	175.672	32859911
AllCCS	[M-H]-	180.393	32859911
DeepCCS	[M-2H]-	218.527	30932474
DeepCCS	[M+Na]+	193.282	30932474
AllCCS	[M+H]+	175.7	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.3	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	180.4	32859911
AllCCS	[M+HCOO]-	180.5	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.	6.02 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2678 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2271.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	654.9 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	573.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1178.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	472.6 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	1414.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	293.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	262.4 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	43.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyestradiol-3-methyl ether	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3	3806.5	Standard polar	33892256
2-Hydroxyestradiol-3-methyl ether	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3	2610.3	Standard non polar	33892256
2-Hydroxyestradiol-3-methyl ether	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3	2819.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyestradiol-3-methyl ether,1TMS,isomer #1	COC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C)CC[C@H]3[C@@H]1CC2	2820.1	Semi standard non polar	33892256
2-Hydroxyestradiol-3-methyl ether,1TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC2	2779.0	Semi standard non polar	33892256
2-Hydroxyestradiol-3-methyl ether,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C)CC[C@H]3[C@@H]1CC2	2774.7	Semi standard non polar	33892256
2-Hydroxyestradiol-3-methyl ether,1TBDMS,isomer #1	COC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC2	3106.9	Semi standard non polar	33892256
2-Hydroxyestradiol-3-methyl ether,1TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC2	3074.4	Semi standard non polar	33892256
2-Hydroxyestradiol-3-methyl ether,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC2	3294.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-2190000000-e6c75d8a52a01c76343b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (2 TMS) - 70eV, Positive	splash10-00lr-2114900000-6f9fb5f37216642ee6da	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Positive-QTOF	splash10-0f79-0197000000-2a3c454db7782949ce0e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Positive-QTOF	splash10-0f79-0692000000-19d694f42b9de8502d21	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Positive-QTOF	splash10-0006-5590000000-3db0854af0439d356587	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Negative-QTOF	splash10-0udi-0029000000-fadd7d5b201334ca856e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Negative-QTOF	splash10-0udi-0079000000-56f2013b7b78f5524223	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Negative-QTOF	splash10-05pc-1090000000-cab4f6333da106d82f96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Negative-QTOF	splash10-0udi-0009000000-4360bacaf95498925fe5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Negative-QTOF	splash10-0udi-0019000000-b5cab14cef0400c3f7b6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Negative-QTOF	splash10-00y0-0090000000-2d9d4c650c6d9ed2dcf9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Positive-QTOF	splash10-0udi-0029000000-1d8e847a4bc26e5c1212	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Positive-QTOF	splash10-0fbi-0694000000-cf79dc2520a1ddc06ac5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Positive-QTOF	splash10-004u-2930000000-305ddbba055983ff8933	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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	0.002348+/-0.0008755 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9812172	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021998

KNApSAcK ID

Not Available

Chemspider ID

500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

39369

Wikipedia Link

Not Available

METLIN ID

5368

PubChem Compound

515

PDB ID

Not Available

ChEBI ID

30835

Food Biomarker Ontology

Not Available

VMH ID

2MCIT

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Gill, Julie C.; Marples, Brian A.; Traynor, John R. Regioselective 2-hydroxylation of 3-methoxyestra-1,3,5(10)-trienes via chromium carbonyl complexes. Tetrahedron Letters (1987), 28(23), 2643-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Clemons M, Goss P: Estrogen and the risk of breast cancer. N Engl J Med. 2001 Jan 25;344(4):276-85. [PubMed:11172156 ]
Gelbke HP, Knuppen R: The excretion of five different 2-hydroxyoestrogen monomethyl ethers in human pregnancy urine. J Steroid Biochem. 1976 Jun-Jul;7(6-7):457-63. [PubMed:966757 ]

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

References

Clemons M, Goss P: Estrogen and the risk of breast cancer. N Engl J Med. 2001 Jan 25;344(4):276-85. [PubMed:11172156 ]

Showing metabocard for 2-Hydroxyestradiol-3-methyl ether (HMDB0000380)

MOL for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

3D MOL for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

3D SDF for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

3D-SDF for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

PDB for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

3D PDB for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

SMILES for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

INCHI for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

Structure for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

3D Structure for HMDB0000380 (2-Hydroxyestradiol-3-methyl ether)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References