NP-MRD: Showing NP-Card for 16b-Hydroxyestradiol (NP0000225)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-09 22:32:56 UTC

NP-MRD ID

NP0000225

Secondary Accession Numbers

None

Natural Product 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>
NP0000225

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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 Mass

288.3814 Da

Monoisotopic Mass

288.17254 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000347

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

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 ]
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. doi: 10.1210/en.2003-0192. [PubMed:12865317 ]
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 NP-Card for 16b-Hydroxyestradiol (NP0000225)

MOL for NP0000225 (16b-Hydroxyestradiol)

3D MOL for NP0000225 (16b-Hydroxyestradiol)

3D SDF for NP0000225 (16b-Hydroxyestradiol)

3D-SDF for NP0000225 (16b-Hydroxyestradiol)

PDB for NP0000225 (16b-Hydroxyestradiol)

3D PDB for NP0000225 (16b-Hydroxyestradiol)

SMILES for NP0000225 (16b-Hydroxyestradiol)

INCHI for NP0000225 (16b-Hydroxyestradiol)

Structure for NP0000225 (16b-Hydroxyestradiol)

3D Structure for NP0000225 (16b-Hydroxyestradiol)