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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000347

Secondary Accession Numbers

HMDB00347

Metabolite Identification

Common Name

16b-Hydroxyestradiol

Description

16b-Hydroxyestradiol, which is better known as epiestriol (or 16beta-epiestriol or 16beta-hydroxy-17beta-estriol), belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, epiestriol is considered to be a steroid molecule. Formally 16b-hydroxyestradiol is a 3-hydroxy steroid that is 17beta-estradiol substituted by a beta-hydroxy group at position 16. In other words, it has hydroxyl groups at the C3, 16-beta, and 17-beta positions. It is an oxidative metabolite of 17beta-estradiol (PMID: 12865317 ). Epiestriol is found in all vertebrates. Epiestriol is a minor and weak endogenous estrogen. It is the 16beta-epimer of estriol (which is 16alpha-hydroxy-17beta-estradiol). Epiestriol has been used clinically in the treatment of acne. In addition to its estrogenic actions, epiestriol has been found to possess significant anti-inflammatory properties without glycogenic activity or immunosuppressive effects (PMID: 9120824 ).

Structure

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

HMDB0000347
     RDKit          3D
16b-Hydroxyestradiol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.2990    1.3988   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007    0.4638    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2052    1.1099    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    1.3943    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089    0.0781    0.5737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2313    0.1480    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740    0.7816    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4306    0.8963    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827    0.3615   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3546    0.4775   -0.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -0.2816   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940   -0.3835   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590   -1.0823   -1.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467   -1.6608   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0119   -0.4927   -0.5947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3219   -0.8212   -0.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3512   -1.3863   -0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -1.2617   -0.0384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7297   -1.0265   -0.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3170   -0.1117    0.9123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3465    0.8260    0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8264    1.1840   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056    1.4890   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032    2.4449   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    2.0960    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591    0.5117    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    2.0364    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    1.8873    1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.6084    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900    1.2185    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677    1.3974    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7710    1.2543   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -0.6995   -2.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -1.9127   -2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -0.3550   -2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091   -2.2534   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -2.2725   -0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3015   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856   -1.4305    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242   -0.7269   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -2.4395   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6579   -2.1742    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -1.4526   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285   -0.4590    1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300    1.5359    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  1
 21 45  1  0
M  END

16b-Hydroxyestradiol .mol
  Mrv1652305261923522D          

 24 27  0  0  0  0            999 V2000
   -2.4762   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1907   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0961   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8808   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.3052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8808    0.9727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1357    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0961    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0473   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  1  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 20  2  0  0  0  0
 12 21  1  1  0  0  0
 19 22  1  6  0  0  0
  9 23  1  1  0  0  0
 10 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000347

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1

> <INCHI_KEY>
PROQIPRRNZUXQM-ZMSHIADSSA-N

> <FORMULA>
C18H24O3

> <MOLECULAR_WEIGHT>
288.3814

> <EXACT_MASS>
288.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.05016500228503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.6705977213333343

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.6240954646046

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.326834303487214

> <JCHEM_PKA_STRONGEST_BASIC>
-3.15653538815926

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
81.26619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000347
     RDKit          3D
16b-Hydroxyestradiol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.2990    1.3988   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007    0.4638    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2052    1.1099    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    1.3943    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089    0.0781    0.5737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2313    0.1480    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740    0.7816    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4306    0.8963    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827    0.3615   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3546    0.4775   -0.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -0.2816   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940   -0.3835   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590   -1.0823   -1.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467   -1.6608   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0119   -0.4927   -0.5947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3219   -0.8212   -0.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3512   -1.3863   -0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -1.2617   -0.0384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7297   -1.0265   -0.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3170   -0.1117    0.9123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3465    0.8260    0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8264    1.1840   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056    1.4890   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032    2.4449   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    2.0960    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591    0.5117    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    2.0364    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    1.8873    1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.6084    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900    1.2185    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677    1.3974    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7710    1.2543   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -0.6995   -2.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -1.9127   -2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -0.3550   -2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091   -2.2534   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -2.2725   -0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3015   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856   -1.4305    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242   -0.7269   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -2.4395   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6579   -2.1742    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -1.4526   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285   -0.4590    1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300    1.5359    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  1
 21 45  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 16b-Hydroxyestradiol .mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.622  -2.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.956  -3.280   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.622  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.289  -0.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.289  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.955  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.621  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.713  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.713  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.046  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.511  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.416   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.511   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.987   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.046   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.046   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.713   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.621   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.621  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.955  -0.970   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.956   0.570   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -0.621  -1.740   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.713   0.570   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.046  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3   20                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19   23                                             
CONECT   10    9   11   15   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20   22                                             
CONECT   20   19    4    6                                                  
CONECT   21   12                                                            
CONECT   22   19                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000347
HETATM    1  C1  UNL     1      -2.299   1.399  -0.691  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.001   0.464   0.425  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.205   1.110   1.522  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.185   1.394   0.938  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.809   0.078   0.574  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.231   0.148   0.258  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.074   0.782   1.146  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.431   0.896   0.932  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.983   0.361  -0.212  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.355   0.477  -0.428  1.00  0.00           O  
HETATM   11  C10 UNL     1       4.161  -0.282  -1.123  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.794  -0.383  -0.883  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.959  -1.082  -1.892  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.747  -1.661  -1.151  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.012  -0.493  -0.595  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.322  -0.821  -0.024  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.351  -1.386  -0.919  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.591  -1.262  -0.038  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.730  -1.027  -0.805  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.317  -0.112   0.912  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.346   0.826   0.830  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.826   1.184  -1.644  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.406   1.489  -0.900  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.003   2.445  -0.386  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.670   2.096   1.735  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.159   0.512   2.430  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.020   2.036   0.042  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.793   1.887   1.712  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.631  -0.608   1.453  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.690   1.218   2.059  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.068   1.397   1.643  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.771   1.254  -0.916  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.599  -0.699  -2.018  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.500  -1.913  -2.386  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.561  -0.355  -2.639  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.109  -2.253  -1.825  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.163  -2.273  -0.318  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.010   0.301  -1.363  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.186  -1.430   0.892  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.524  -0.727  -1.787  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.178  -2.440  -1.219  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.658  -2.174   0.557  1.00  0.00           H  
HETATM   43  H22 UNL     1      -5.479  -1.453  -0.351  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.229  -0.459   1.962  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.130   1.536   1.498  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   16   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7    7   12
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   11
CONECT   10   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   38
CONECT   16   17   39
CONECT   17   18   40   41
CONECT   18   19   20   42
CONECT   19   43
CONECT   20   21   44
CONECT   21   45
END

HMDB0000347
     RDKit          3D
16b-Hydroxyestradiol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.2990    1.3988   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007    0.4638    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2052    1.1099    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    1.3943    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089    0.0781    0.5737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2313    0.1480    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740    0.7816    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4306    0.8963    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827    0.3615   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3546    0.4775   -0.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -0.2816   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940   -0.3835   -0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590   -1.0823   -1.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467   -1.6608   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0119   -0.4927   -0.5947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3219   -0.8212   -0.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3512   -1.3863   -0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -1.2617   -0.0384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7297   -1.0265   -0.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3170   -0.1117    0.9123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3465    0.8260    0.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8264    1.1840   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056    1.4890   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0032    2.4449   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    2.0960    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591    0.5117    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    2.0364    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    1.8873    1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.6084    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900    1.2185    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677    1.3974    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7710    1.2543   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -0.6995   -2.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -1.9127   -2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -0.3550   -2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091   -2.2534   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630   -2.2725   -0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3015   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856   -1.4305    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242   -0.7269   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -2.4395   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6579   -2.1742    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -1.4526   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285   -0.4590    1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1300    1.5359    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  6
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  1
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16-Epiestriol	ChEBI
16beta,17beta-Estriol	ChEBI
Actriol	ChEBI
Epiestriol	ChEBI
Epiestriolum	ChEBI
Epioestriolum	ChEBI
Estra-1,3,5(10)-triene-3,16beta,17-triol	ChEBI
Estra-1,3,5(10)-triene-3,16beta,17beta-triol	ChEBI
16b,17b-Estriol	Generator
16Β,17β-estriol	Generator
Estra-1,3,5(10)-triene-3,16b,17-triol	Generator
Estra-1,3,5(10)-triene-3,16β,17-triol	Generator
Estra-1,3,5(10)-triene-3,16b,17b-triol	Generator
Estra-1,3,5(10)-triene-3,16β,17β-triol	Generator
16beta-Hydroxy-17beta-estradiol	HMDB
16b-Hydroxy-17b-estradiol	HMDB
16Β-hydroxy-17β-estradiol	HMDB
16-Epi-estriol	HMDB
16-Epiestratriol	HMDB
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	HMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	HMDB
16 alpha Hydroxy estradiol	HMDB
16-alpha-Hydroxy-estradiol	HMDB
16alpha,17beta Estriol	HMDB
16alpha,17beta-Estriol	HMDB
16beta Hydroxy estradiol	HMDB
16beta-Hydroxy-estradiol	HMDB
Estriol	HMDB
Ovestin	HMDB
16Β-hydroxyestradiol	HMDB
16b-Hydroxyestradiol	Generator

Chemical Formula

C₁₈H₂₄O₃

Average Molecular Weight

288.3814

Monoisotopic Molecular Weight

288.172544634

IUPAC Name

(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

Traditional Name

(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

CAS Registry Number

547-81-9

SMILES

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

InChI Identifier

InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1

InChI Key

PROQIPRRNZUXQM-ZMSHIADSSA-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
16-hydroxysteroid
16-beta-hydroxysteroid
Hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
1,2-diol
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:87620 )
16beta-hydroxy steroid (CHEBI:87620 )
C18 steroids (estrogens) and derivatives (LMST02010006 )

Ontology

Not Available

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	153.573	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001228

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.27 m³·mol⁻¹	ChemAxon
Polarizability	33.05 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]+	168.847	31661259
DarkChem	[M-H]-	166.198	31661259
AllCCS	[M+H]+	171.42	32859911
AllCCS	[M-H]-	175.988	32859911
DeepCCS	[M-2H]-	213.807	30932474
DeepCCS	[M+Na]+	188.626	30932474
AllCCS	[M+H]+	171.4	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	176.0	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16b-Hydroxyestradiol	[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3943.9	Standard polar	33892256
16b-Hydroxyestradiol	[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2917.3	Standard non polar	33892256
16b-Hydroxyestradiol	[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2941.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16b-Hydroxyestradiol,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)[C@@H]2O	2789.2	Semi standard non polar	33892256
16b-Hydroxyestradiol,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@H](O)[C@@H]2O[Si](C)(C)C	2794.1	Semi standard non polar	33892256
16b-Hydroxyestradiol,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O)[C@@H]2O	2771.9	Semi standard non polar	33892256
16b-Hydroxyestradiol,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)[C@@H]2O	2842.9	Semi standard non polar	33892256
16b-Hydroxyestradiol,2TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2782.1	Semi standard non polar	33892256
16b-Hydroxyestradiol,2TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O)[C@@H]2O[Si](C)(C)C	2842.9	Semi standard non polar	33892256
16b-Hydroxyestradiol,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2907.4	Semi standard non polar	33892256
16b-Hydroxyestradiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O	3065.1	Semi standard non polar	33892256
16b-Hydroxyestradiol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C	3081.3	Semi standard non polar	33892256
16b-Hydroxyestradiol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O)[C@@H]2O	3084.3	Semi standard non polar	33892256
16b-Hydroxyestradiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O	3374.5	Semi standard non polar	33892256
16b-Hydroxyestradiol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C	3303.1	Semi standard non polar	33892256
16b-Hydroxyestradiol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C	3391.4	Semi standard non polar	33892256
16b-Hydroxyestradiol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C	3664.8	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 - 16b-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-1590000000-cf2f42c37e3436edbcfa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (3 TMS) - 70eV, Positive	splash10-009i-2033900000-46c301a46b654b6c6bf3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_3_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 - 16b-Hydroxyestradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0290000000-c1aaa2c05e9fd0323ef6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 16b-Hydroxyestradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-2900000000-3b5302633684d0176de2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 16b-Hydroxyestradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-7900000000-1705b9f7f2b39ae9ba41	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Positive-QTOF	splash10-000i-0090000000-11e0a31c4649eeadffb4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Positive-QTOF	splash10-0fki-0490000000-4179a69250f74019b4f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Positive-QTOF	splash10-0fvi-4970000000-09555c37e0926cc7a845	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Negative-QTOF	splash10-000i-0090000000-78e3342aed99bfff3970	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Negative-QTOF	splash10-000i-0090000000-66743ac1a583b78756a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Negative-QTOF	splash10-062l-0090000000-a38189a9216fbf580f8c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Negative-QTOF	splash10-000i-0090000000-843a74fabb1d0eb512a1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Negative-QTOF	splash10-00kr-0090000000-4e0854fb8be9cf34de97	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Negative-QTOF	splash10-02br-0090000000-70686fa9219ae093945a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Positive-QTOF	splash10-000i-0090000000-1126a56061a8c854c755	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Positive-QTOF	splash10-0fga-0790000000-a1dba0b6195890b30d91	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Positive-QTOF	splash10-0a6v-3910000000-64d9abb8f215c1264e1f	2021-09-25	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

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 but not Quantified	Not Quantified	Not Available	Not Available	Normal	21543078	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

FDB021970

KNApSAcK ID

Not Available

Chemspider ID

62155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5336

PubChem Compound

68929

PDB ID

Not Available

ChEBI ID

87620

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ling, Yangzhi; Xu, Chunfang; Fang, Guofu; Liu, Weiqin. Improved synthesis of estriol via hydroboration. Yiyao Gongye (1988), 19(12), 533-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Lee AJ, Cai MX, Thomas PE, Conney AH, Zhu BT: Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98. [PubMed:12865317 ]
Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]
Nambara T, Matsuki Y, Igarashi J, Kawarada Y, Kurata M: Studies on steroid conjugates. XII. Occurrence of 16-epiestriol 16-glucuronide in human pregnancy urine. Chem Pharm Bull (Tokyo). 1974 Oct;22(10):2242-5. [PubMed:4377544 ]
Adlercreutz H, Martin F, Pulkkinen M, Dencker H, Rimer U, Sjoberg NO, Tikkanen MJ: Intestinal metabolism of estrogens. J Clin Endocrinol Metab. 1976 Sep;43(3):497-505. [PubMed:956337 ]
Latman NS, Kishore V, Bruot BC: 16-epiestriol: an anti-inflammatory steroid without glycogenic activity. J Pharm Sci. 1994 Jun;83(6):874-7. doi: 10.1002/jps.2600830623. [PubMed:9120824 ]

Showing metabocard for 16b-Hydroxyestradiol (HMDB0000347)

MOL for HMDB0000347 (16b-Hydroxyestradiol)

3D MOL for HMDB0000347 (16b-Hydroxyestradiol)

3D SDF for HMDB0000347 (16b-Hydroxyestradiol)

3D-SDF for HMDB0000347 (16b-Hydroxyestradiol)

PDB for HMDB0000347 (16b-Hydroxyestradiol)

3D PDB for HMDB0000347 (16b-Hydroxyestradiol)

SMILES for HMDB0000347 (16b-Hydroxyestradiol)

INCHI for HMDB0000347 (16b-Hydroxyestradiol)

Structure for HMDB0000347 (16b-Hydroxyestradiol)

3D Structure for HMDB0000347 (16b-Hydroxyestradiol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra