Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000313

Secondary Accession Numbers

HMDB00313

Metabolite Identification

Common Name

16b-Hydroxyestrone

Description

16b-Hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16b-hydroxyestrone is considered to be a steroid lipid molecule. 16b-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0000313
     RDKit          3D
16b-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.1711   -0.6700    1.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461   -0.6129    0.2561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6898   -1.8215   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -1.9129   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -0.6954   -0.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9373   -0.7216   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -1.8304    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9451   -1.8039    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6665   -0.6311    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.5356    0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0072    0.4712   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492    0.4509   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    1.6797   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    1.7329   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    0.5939   -0.0150 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5110    0.5756   -0.3248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3271    1.7172    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    1.2183   -0.1084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6303    1.6631    0.8481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.2863   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -0.9986   -0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    0.2277    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894   -0.7305    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6160   -1.5428    2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1885   -2.7584   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8161   -1.6717   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -2.7708   -0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998   -2.1611    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4406   -0.6132   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -2.7660    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -2.6700    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3149   -0.2728    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835    1.3986   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4110    1.8416   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    2.5625   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416    1.7114   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    2.7093   -0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1428    0.6735    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283    0.4899   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603    2.0292    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670    2.6407   -0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.5109   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345    2.5794    0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  2  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  6
  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  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
M  END

16b-Hydroxyestrone.mol
  Mrv0541 02231218272D          

 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  0  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  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 20  2  0  0  0  0
 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>
HMDB0000313

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1

> <INCHI_KEY>
WPOCIZJTELRQMF-LFRCEIEQSA-N

> <FORMULA>
C18H22O3

> <MOLECULAR_WEIGHT>
286.3655

> <EXACT_MASS>
286.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.28941615982396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.4379631133333346

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.38257874741176

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.326567997010477

> <JCHEM_PKA_STRONGEST_BASIC>
-3.506418620839579

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
80.57459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16 α-hydroxyestrone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000313
     RDKit          3D
16b-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.1711   -0.6700    1.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461   -0.6129    0.2561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6898   -1.8215   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -1.9129   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -0.6954   -0.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9373   -0.7216   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -1.8304    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9451   -1.8039    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6665   -0.6311    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.5356    0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0072    0.4712   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492    0.4509   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    1.6797   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    1.7329   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    0.5939   -0.0150 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5110    0.5756   -0.3248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3271    1.7172    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    1.2183   -0.1084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6303    1.6631    0.8481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.2863   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -0.9986   -0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    0.2277    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894   -0.7305    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6160   -1.5428    2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1885   -2.7584   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8161   -1.6717   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -2.7708   -0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998   -2.1611    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4406   -0.6132   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -2.7660    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -2.6700    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3149   -0.2728    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835    1.3986   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4110    1.8416   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    2.5625   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416    1.7114   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    2.7093   -0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1428    0.6735    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283    0.4899   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603    2.0292    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670    2.6407   -0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.5109   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345    2.5794    0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  2  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  6
  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  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 16b-Hydroxyestrone.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         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    HMDB0000313
HETATM    1  C1  UNL     1      -2.171  -0.670   1.751  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.246  -0.613   0.256  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.690  -1.822  -0.421  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.232  -1.913  -0.142  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.528  -0.695  -0.571  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.937  -0.722  -0.217  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.607  -1.830   0.257  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.945  -1.804   0.579  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.667  -0.631   0.427  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.018  -0.536   0.733  1.00  0.00           O  
HETATM   11  C10 UNL     1       4.007   0.471  -0.043  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.649   0.451  -0.371  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.033   1.680  -0.866  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.556   1.733  -0.793  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.070   0.594  -0.015  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.511   0.576  -0.325  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.327   1.717   0.134  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.737   1.218  -0.108  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.630   1.663   0.848  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.645  -0.286  -0.132  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.567  -0.999  -0.418  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.683   0.228   2.192  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.189  -0.730   2.189  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.616  -1.543   2.142  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.188  -2.758  -0.118  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.816  -1.672  -1.521  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.176  -2.771  -0.713  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.100  -2.161   0.927  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.441  -0.613  -1.675  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.082  -2.766   0.390  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.461  -2.670   0.948  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.315  -0.273   1.658  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.583   1.399  -0.161  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.411   1.842  -1.916  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.442   2.563  -0.292  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.142   1.711  -1.826  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.187   2.709  -0.362  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.143   0.673   1.070  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.628   0.490  -1.438  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.160   2.029   1.171  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.167   2.641  -0.493  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.020   1.511  -1.138  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.934   2.579   0.584  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   21
END

HMDB0000313
     RDKit          3D
16b-Hydroxyestrone
 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.1711   -0.6700    1.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461   -0.6129    0.2561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6898   -1.8215   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -1.9129   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282   -0.6954   -0.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9373   -0.7216   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -1.8304    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9451   -1.8039    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6665   -0.6311    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.5356    0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0072    0.4712   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492    0.4509   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    1.6797   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    1.7329   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    0.5939   -0.0150 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5110    0.5756   -0.3248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3271    1.7172    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372    1.2183   -0.1084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6303    1.6631    0.8481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.2863   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -0.9986   -0.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    0.2277    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894   -0.7305    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6160   -1.5428    2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1885   -2.7584   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8161   -1.6717   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -2.7708   -0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998   -2.1611    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4406   -0.6132   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -2.7660    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -2.6700    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3149   -0.2728    1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835    1.3986   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4110    1.8416   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    2.5625   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416    1.7114   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    2.7093   -0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1428    0.6735    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283    0.4899   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603    2.0292    1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670    2.6407   -0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.5109   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345    2.5794    0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  2  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  6
  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  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(16beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one	ChEBI
16-Hydroxyestrone	ChEBI
3,16-Dihydroxyestra-1,3,5(10)-trien-17-one	ChEBI
3,16beta-Dihydroxy-estra-1,3,5(10)-trien-17-one	ChEBI
(16b)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one	Generator
(16Β)-3,16-dihydroxyestra-1,3,5(10)-trien-17-one	Generator
3,16b-Dihydroxy-estra-1,3,5(10)-trien-17-one	Generator
3,16Β-dihydroxy-estra-1,3,5(10)-trien-17-one	Generator
16alpha-Hydroxyestrone	HMDB
16beta-Hydroxyestrone	HMDB
3,16-Dihydroxy-estra-1,3,5(10)-trien-17-one	HMDB
16 alpha-Hydroxyestrone	HMDB
16 beta-Hydroxyestrone	HMDB
16-alpha-Hydroxyestrone	HMDB

Chemical Formula

C₁₈H₂₂O₃

Average Molecular Weight

286.3655

Monoisotopic Molecular Weight

286.15689457

IUPAC Name

(1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

Traditional Name

16 α-hydroxyestrone

CAS Registry Number

966-06-3

SMILES

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

InChI Identifier

InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1

InChI Key

WPOCIZJTELRQMF-LFRCEIEQSA-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
Hydroxysteroid
17-oxosteroid
Oxosteroid
16-beta-hydroxysteroid
16-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Ketone
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:87628 )
16beta-hydroxy steroid (CHEBI:87628 )
C18 steroids (estrogens) and derivatives (LMST02010046 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0000313)
Extracellular (HMDB: HMDB0000313)

Biofluid or Excreta

Urine (HMDB: HMDB0000313)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000313)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000313)

Source

Endogenous

Endogenous (HMDB: HMDB0000313)

Animal

Animal (HMDB: HMDB0000313)

Exogenous

Food

Food (HMDB: HMDB0000313)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Venison

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

Bovine

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000313)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000313)

Cellular process

Cell signaling (HMDB: HMDB0000313)

System process

Reproduction (HMDB: HMDB0000313)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000313)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000313)

Molecular messenger

Hormone (HMDB: HMDB0000313)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000313)

Emulsifier (HMDB: HMDB0000313)

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	0.047 g/L	ALOGPS
logP	2.45	ALOGPS
logP	3.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.57 m³·mol⁻¹	ChemAxon
Polarizability	32.29 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]+	168.721	31661259
DarkChem	[M-H]-	166.199	31661259
AllCCS	[M+H]+	169.911	32859911
AllCCS	[M-H]-	175.541	32859911
DeepCCS	[M-2H]-	212.982	30932474
DeepCCS	[M+Na]+	187.834	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	175.5	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16b-Hydroxyestrone	[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3438.6	Standard polar	33892256
16b-Hydroxyestrone	[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2824.6	Standard non polar	33892256
16b-Hydroxyestrone	[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2829.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16b-Hydroxyestrone,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)C2=O	2768.0	Semi standard non polar	33892256
16b-Hydroxyestrone,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O)C2=O	2786.1	Semi standard non polar	33892256
16b-Hydroxyestrone,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C	2768.1	Semi standard non polar	33892256
16b-Hydroxyestrone,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)C2=O	2875.1	Semi standard non polar	33892256
16b-Hydroxyestrone,2TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2779.4	Semi standard non polar	33892256
16b-Hydroxyestrone,2TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C	2839.0	Semi standard non polar	33892256
16b-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2905.4	Semi standard non polar	33892256
16b-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2783.1	Standard non polar	33892256
16b-Hydroxyestrone,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2899.0	Standard polar	33892256
16b-Hydroxyestrone,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)C1=O	3049.5	Semi standard non polar	33892256
16b-Hydroxyestrone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](O)C[C@@H]12	3088.5	Semi standard non polar	33892256
16b-Hydroxyestrone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C	3043.6	Semi standard non polar	33892256
16b-Hydroxyestrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]12	3412.8	Semi standard non polar	33892256
16b-Hydroxyestrone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]2C1	3287.1	Semi standard non polar	33892256
16b-Hydroxyestrone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	3331.5	Semi standard non polar	33892256
16b-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1	3616.3	Semi standard non polar	33892256
16b-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1	3466.0	Standard non polar	33892256
16b-Hydroxyestrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1	3214.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-2690000000-4da4066a9998d4bb7152	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positive	splash10-016r-3279600000-35209b189461208c9804	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_2_3) - 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 - 16b-Hydroxyestrone 10V, Positive-QTOF	splash10-000i-0090000000-ea49b0e7c1a26f8807b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Positive-QTOF	splash10-0ap0-0490000000-7a9632ca2f7369b28ad3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Positive-QTOF	splash10-0gb9-7980000000-f674402195ec376faeb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Negative-QTOF	splash10-000i-0090000000-91f32a5e866ea149a4a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Negative-QTOF	splash10-000i-0090000000-f8524ff8a5fae66251ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Negative-QTOF	splash10-02dl-1090000000-5ac386a35fc2bb3cc1f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Positive-QTOF	splash10-000i-0090000000-8269f9806e3a6460adb9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Positive-QTOF	splash10-00ks-0590000000-2d8e09d2baef368efec1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Positive-QTOF	splash10-00dj-0920000000-bce8e0246e58d9e59bbd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Negative-QTOF	splash10-000i-0090000000-fcaf0435bbf678a207f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Negative-QTOF	splash10-000i-0090000000-48bccddc063fe7e2f998	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Negative-QTOF	splash10-02di-0090000000-080f7d164203318ad338	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB021940

KNApSAcK ID

Not Available

Chemspider ID

17215934

KEGG Compound ID

C05300

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5302

PubChem Compound

22833517

PDB ID

Not Available

ChEBI ID

87628

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Biggerstaff, W. R.; Gallagher, T. F. 3,16b-Dihydroxy-1,3,5-estratrien-17-one and related compounds. Journal of Organic Chemistry (1957), 22 1220-2.

Material Safety Data Sheet (MSDS)

Not Available

General References

Yokoyama K, Tajima M, Yoshida H, Nakayama M, Tokutome G, Sakagami H, Hosoya T: Plasma pteridine concentrations in patients with chronic renal failure. Nephrol Dial Transplant. 2002 Jun;17(6):1032-6. [PubMed:12032193 ]

Enzymes

Enzyme Details

1. Estradiol 17-beta-dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:: HSD17B2
Uniprot ID:: P37059
Molecular weight:: 42784.75

Reactions

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

2. Estradiol 17-beta-dehydrogenase 8

General function:: Involved in oxidoreductase activity
Specific function:: NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:: HSD17B8
Uniprot ID:: Q92506
Molecular weight:: 26973.56

Reactions

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

3. Estradiol 17-beta-dehydrogenase 1

General function:: Involved in estradiol 17-beta-dehydrogenase activity
Specific function:: Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:: HSD17B1
Uniprot ID:: P14061
Molecular weight:: 34949.715

Reactions

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

4. 3-keto-steroid reductase

General function:: Involved in oxidoreductase activity
Specific function:: Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:: HSD17B7
Uniprot ID:: P56937
Molecular weight:: 38205.77

Reactions

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

5. 17-beta-hydroxysteroid dehydrogenase type 6

General function:: Involved in oxidoreductase activity
Specific function:: NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids.
Gene Name:: HSD17B6
Uniprot ID:: O14756
Molecular weight:: 35965.41

Reactions

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

6. Estradiol 17-beta-dehydrogenase 12

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of estrone (E1) into estradiol (E2), suggesting a central role in estrogen formation. Its strong expression in ovary and mammary gland suggest that it may constitute the major enzyme responsible for the conversion of E1 to E2 in women. Also has 3-ketoacyl-CoA reductase activity, reducing both long chain 3-ketoacyl-CoAs and long chain fatty acyl-CoAs, suggesting a role in long fatty acid elongation.
Gene Name:: HSD17B12
Uniprot ID:: Q53GQ0
Molecular weight:: 34323.875

Reactions

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Showing metabocard for 16b-Hydroxyestrone (HMDB0000313)

MOL for HMDB0000313 (16b-Hydroxyestrone)

3D MOL for HMDB0000313 (16b-Hydroxyestrone)

3D SDF for HMDB0000313 (16b-Hydroxyestrone)

3D-SDF for HMDB0000313 (16b-Hydroxyestrone)

PDB for HMDB0000313 (16b-Hydroxyestrone)

3D PDB for HMDB0000313 (16b-Hydroxyestrone)

SMILES for HMDB0000313 (16b-Hydroxyestrone)

INCHI for HMDB0000313 (16b-Hydroxyestrone)

Structure for HMDB0000313 (16b-Hydroxyestrone)

3D Structure for HMDB0000313 (16b-Hydroxyestrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions