NP-MRD: Showing NP-Card for Estradiol (NP0001268)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:14 UTC

NP-MRD ID

NP0001268

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estradiol

Description

Estradiol is the most potent form of mammalian estrogenic steroids. Estradiol is produced in the ovaries. The ovary requires both luteinizing hormone (LH) and follicle-stimulating hormone (FSH) to produce sex steroids. LH stimulates the cells surrounding the follicle to produce progesterone and androgens. The androgens diffuse across the basement membrane to the granulosa cell layer, where, under the action of FSH, they are aromatized to estrogens, mainly estradiol. The ovary shows cyclical activity, unlike the testis that is maintained in a more or less constant state of activity. Hormone secretions vary according to the phase of the menstrual cycle. In the developing follicle LH receptors (LH-R) are only located on the thecal cells and FSH receptors (FSHR) on the granulosa cells. The dominant pre-ovulatory follicle develops LH-Rs on the granulosa cells prior to the LH surge. Thecal cells of the preovulatory follicle also develop the capacity to synthesize estradiol and this persists when the thecal cells become incorporated into the corpus luteum. After ovulation, the empty follicle is remodelled and plays an important role in the second half or luteal phase of the menstrual cycle. This phase is dominated by progesterone and, to a lesser extent, estradiol secretion by the corpus luteum. Estradiol is also synthesized locally from cholesterol through testosterone in the hippocampus and acts rapidly to modulate neuronal synaptic plasticity. Localization of estrogen receptor alpha (ERalpha) in spines in addition to nuclei of principal neurons implies that synaptic ERalpha is responsible for rapid modulation of synaptic plasticity by endogenous estradiol. Estradiol is a potent endogenous antioxidant which suppresses hepatic fibrosis in animal models, and attenuates induction of redox sensitive transcription factors, hepatocyte apoptosis and hepatic stellate cells activation by inhibiting a generation of reactive oxygen species in primary cultures. This suggests that the greater progression of hepatic fibrosis and hepatocellular carcinoma in men and postmenopausal women may be due, at least in part, to lower production of estradiol and a reduced response to the action of estradiol. Estradiol has been reported to induce the production of interferon (INF)-gamma in lymphocytes, and augments an antigen-specific primary antibody response in human peripheral blood mononuclear cells. IFN-gamma is a potent cytokine with immunomodulatory and antiproliferative properties. Therefore, female subjects, particularly before menopause, may produce antibodies against hepatitis B virus e antigen and hepatitis B virus surface antigen at a higher frequency than males with chronic hepatitis B virus infection. The estradiol-Dihydrotestosterone model of prostate cancer (PC) proposes that the first step in the development of most PC and breast cancer (BC) occurs when aromatase converts testosterone to estradiol. (PMID: 17708600 , 17678531 , 17644764 ).

Structure

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


  Mrv1652306212100063D          

 44 47  0  0  0  0            999 V2000
   -2.8825    1.0775   -2.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    1.0353   -1.2617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8215    2.1698   -0.8041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3587    1.9191   -1.2183 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1754    0.5236   -0.7976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6072    0.2194   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2695   -0.3511   -1.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5458   -0.6715   -2.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1957   -0.2896   -0.6972 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.0431    1.9292   -1.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9265    0.9436   -3.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820    2.0452   -3.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9132    1.7928   -0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
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  6 12  1  0  0  0  0
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  3 24  1  0  0  0  0
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  4 27  1  0  0  0  0
 16 38  1  1  0  0  0
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 10 31  1  0  0  0  0
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  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

HMDB0000151
     RDKit          3D
Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.5652   -1.3102   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384    0.0393   -0.6712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3206    0.0127   -1.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.5652   -1.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308    0.2518   -0.6097 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1248   -0.1107   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -0.1061   -1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.4369   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -0.7829   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903   -1.1201    0.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9652   -0.7897    1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.4589    0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -0.4887    2.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    0.5583    1.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1176    0.1054    0.6665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3662    0.8226    0.3927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3612    0.9347    1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6596    1.2000    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4388    0.2089   -1.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892   -1.4149   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521   -2.0915   -0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -1.5941    0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    1.0147   -2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -0.6532   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.6200   -2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0990   -1.5898   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6616    0.1590   -2.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8715   -0.3916    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -1.0668    2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -0.3031    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957   -1.4710    2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1240    1.5669    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9565    2.2665    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1
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 16  2  1  0
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 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
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  3 24  1  0
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M  END


  Mrv1652306212100063D          

 44 47  0  0  0  0            999 V2000
   -2.8825    1.0775   -2.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    1.0353   -1.2617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8215    2.1698   -0.8041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3587    1.9191   -1.2183 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1754    0.5236   -0.7976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6072    0.2194   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742    1.2380   -1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8961    0.9582   -1.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2695   -0.3511   -1.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5458   -0.6715   -2.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450   -1.3807   -1.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
  5 28  1  1  0  0  0
 15 37  1  6  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
 16 38  1  1  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  1  0  0  0
 10 31  1  0  0  0  0
 20 44  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001268

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])[C@@]1([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

> <INCHI_KEY>
VOXZDWNPVJITMN-ZBRFXRBCSA-N

> <FORMULA>
C18H24O2

> <MOLECULAR_WEIGHT>
272.382

> <EXACT_MASS>
272.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.12316248072682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.745501328333334

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37769223665565

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.327060716263132

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839974156894889

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
79.9047

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000151
     RDKit          3D
Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.5652   -1.3102   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384    0.0393   -0.6712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3206    0.0127   -1.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.5652   -1.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308    0.2518   -0.6097 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1248   -0.1107   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -0.1061   -1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.4369   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -0.7829   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903   -1.1201    0.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9652   -0.7897    1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.4589    0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -0.4887    2.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    0.5583    1.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1176    0.1054    0.6665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3662    0.8226    0.3927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3612    0.9347    1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6596    1.2000    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3607    0.9095   -0.7501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4388    0.2089   -1.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892   -1.4149   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521   -2.0915   -0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -1.5941    0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    1.0147   -2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -0.6532   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.6200   -2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0990   -1.5898   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163    1.3330   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6616    0.1590   -2.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -0.4364   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715   -0.3916    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -1.0668    2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -0.3031    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957   -1.4710    2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1240    1.5669    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    0.5286    2.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401   -1.0123    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    1.8048   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    1.8144    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200   -0.0032    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    2.2665    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    0.5480    1.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1562    1.8395   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9661    0.8986   -1.8166 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
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 20 44  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.882   1.077  -2.805  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.746   1.035  -1.262  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.821   2.170  -0.804  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.359   1.919  -1.218  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.175   0.524  -0.798  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.607   0.219  -1.234  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.574   1.238  -1.322  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.896   0.958  -1.680  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.269  -0.351  -1.940  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.546  -0.672  -2.296  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.345  -1.381  -1.840  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.015  -1.112  -1.473  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.056  -2.276  -1.405  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.269  -1.950  -0.722  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.801  -0.611  -1.234  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.196  -0.290  -0.697  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.334  -1.278  -0.935  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.607  -0.434  -0.739  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.138   1.028  -0.602  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.043   1.929  -1.209  0.00  0.00           O+0
HETATM   21  H   UNK     0      -1.927   0.944  -3.318  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.282   2.045  -3.131  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.559   0.307  -3.187  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.859   2.265   0.289  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.159   3.132  -1.208  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.244   2.710  -0.757  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.249   2.047  -2.302  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.210   0.526   0.303  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.319   2.272  -1.108  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.611   1.772  -1.744  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.069   0.146  -2.332  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.663  -2.400  -2.047  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.527  -3.114  -0.875  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.857  -2.607  -2.432  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.977  -2.762  -0.921  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.129  -1.909   0.366  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.834  -0.666  -2.330  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.102  -0.193   0.398  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.303  -1.691  -1.949  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.302  -2.117  -0.234  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.297  -0.569  -1.579  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.144  -0.742   0.166  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.063   1.290   0.461  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.913   1.793  -0.796  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3   16   19    1                                             
CONECT    3    2    4   24   25                                             
CONECT    4    5    3   26   27                                             
CONECT    5    4    6   15   28                                             
CONECT    6    7   12    5                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9   31                                                       
CONECT   11    9   12   32                                                  
CONECT   12    6   11   13                                                  
CONECT   13   12   14   33   34                                             
CONECT   14   13   15   35   36                                             
CONECT   15   16   14    5   37                                             
CONECT   16   15    2   17   38                                             
CONECT   17   16   18   39   40                                             
CONECT   18   17   19   41   42                                             
CONECT   19   18    2   20   43                                             
CONECT   20   19   44                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   13                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

COMPND    HMDB0000151
HETATM    1  C1  UNL     1      -2.565  -1.310  -0.186  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.138   0.039  -0.671  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.321   0.013  -1.912  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.045  -0.565  -1.654  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.731   0.252  -0.610  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.125  -0.111  -0.345  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.009  -0.106  -1.404  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.351  -0.437  -1.242  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.843  -0.783  -0.005  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.190  -1.120   0.185  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.965  -0.790   1.058  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.627  -0.459   0.891  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.740  -0.489   2.081  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.667   0.558   1.859  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.118   0.105   0.667  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.366   0.823   0.393  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.361   0.935   1.469  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.660   1.200   0.715  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.361   0.910  -0.750  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.439   0.209  -1.302  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.689  -1.415  -0.144  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.252  -2.091  -0.932  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.195  -1.594   0.794  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.259   1.015  -2.358  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.826  -0.653  -2.660  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.614  -0.620  -2.606  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.099  -1.590  -1.248  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.616   1.333  -0.912  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.662   0.159  -2.387  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.054  -0.436  -2.068  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.871  -0.392   0.417  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.374  -1.067   2.032  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.313  -0.303   3.010  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.196  -1.471   2.136  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.124   1.567   1.712  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.005   0.529   2.737  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.240  -1.012   0.775  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.134   1.805  -0.076  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.123   1.814   2.101  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.420  -0.003   2.051  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.956   2.266   0.775  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.479   0.548   1.089  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.156   1.839  -1.312  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.966   0.899  -1.817  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   16   19
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   15   28
CONECT    6    7    7   12
CONECT    7    8   29
CONECT    8    9    9   30
CONECT    9   10   11
CONECT   10   31
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   37
CONECT   16   17   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   20   43
CONECT   20   44
END

HMDB0000151
     RDKit          3D
Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.5652   -1.3102   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384    0.0393   -0.6712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3206    0.0127   -1.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.5652   -1.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308    0.2518   -0.6097 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1248   -0.1107   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -0.1061   -1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.4369   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -0.7829   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903   -1.1201    0.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9652   -0.7897    1.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.4589    0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -0.4887    2.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    0.5583    1.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1176    0.1054    0.6665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3662    0.8226    0.3927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3612    0.9347    1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6596    1.2000    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3607    0.9095   -0.7501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4388    0.2089   -1.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892   -1.4149   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521   -2.0915   -0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -1.5941    0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    1.0147   -2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -0.6532   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -0.6200   -2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0990   -1.5898   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163    1.3330   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6616    0.1590   -2.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -0.4364   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8715   -0.3916    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -1.0668    2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -0.3031    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957   -1.4710    2.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1240    1.5669    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    0.5286    2.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401   -1.0123    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    1.8048   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    1.8144    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200   -0.0032    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    2.2665    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    0.5480    1.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1562    1.8395   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9661    0.8986   -1.8166 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
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 20 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(17beta)-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
17beta Oestradiol	ChEBI
17beta-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
17beta-Oestradiol	ChEBI
beta-Estradiol	ChEBI
cis-Estradiol	ChEBI
Estradiol-17beta	ChEBI
Climara	Kegg
Divigel	Kegg
Estrace	Kegg
Estraderm	Kegg
Estrasorb	Kegg
Estring	Kegg
Estrogel	Kegg
Innofem	Kegg
Vagifem	Kegg
Vivelle	Kegg
(17b)-Estra-1,3,5(10)-triene-3,17-diol	Generator
(17Β)-estra-1,3,5(10)-triene-3,17-diol	Generator
17b Oestradiol	Generator
17Β oestradiol	Generator
17b-Estra-1,3,5(10)-triene-3,17-diol	Generator
17Β-estra-1,3,5(10)-triene-3,17-diol	Generator
17b-Oestradiol	Generator
17Β-oestradiol	Generator
b-Estradiol	Generator
Β-estradiol	Generator
Estradiol-17b	Generator
Estradiol-17β	Generator
(+)-3,17b-Estradiol	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol	HMDB
17b-Estradiol	HMDB
3,17-Epidihydroxyestratriene	HMDB
3,17b-Dihydroxyestra-1,3,5(10)-triene	HMDB
3,17b-Estradiol	HMDB
Aerodiol	HMDB
Agofollin	HMDB
Altrad	HMDB
Amnestrogen	HMDB
Aquadiol	HMDB
Bardiol	HMDB
Climaderm	HMDB
Compudose	HMDB
Corpagen	HMDB
D-Estradiol	HMDB
D-Oestradiol	HMDB
delta-Estradiol	HMDB
delta-Oestradiol	HMDB
Dermestril	HMDB
Dihydro-theelin	HMDB
Dihydrofollicular hormone	HMDB
Dihydrofolliculin	HMDB
Dihydromenformon	HMDB
Dihydrotheelin	HMDB
Dihydroxyestrin	HMDB
Dimenformon	HMDB
Diogyn	HMDB
Diogynets	HMDB
Encore	HMDB
Epiestriol 50	HMDB
Estra-1,3,5(10)-triene-3,17b-diol	HMDB
Estraderm TTS	HMDB
Estradiol-17-beta	HMDB
Estradot	HMDB
Estraldine	HMDB
Estring vaginal ring	HMDB
Estroclim	HMDB
Estroclim 50	HMDB
Estrogel HBF	HMDB
Estrovite	HMDB
Evorel	HMDB
Femestral	HMDB
Femogen	HMDB
Follicyclin	HMDB
Gelestra	HMDB
Ginosedol	HMDB
Gynergon	HMDB
Gynoestryl	HMDB
Lamdiol	HMDB
Macrodiol	HMDB
Menorest	HMDB
Nordicol	HMDB
Oesclim	HMDB
Oestergon	HMDB
Oestra-1,3,5(10)-triene-3,17b-diol	HMDB
Oestradiol	HMDB
Oestrogel	HMDB
Oestroglandol	HMDB
Ovahormon	HMDB
Ovasterol	HMDB
Ovastevol	HMDB
Ovocyclin	HMDB
Ovocylin	HMDB
Perlatanol	HMDB
Primofol	HMDB
Profoliol	HMDB
Profoliol b	HMDB
Progynon	HMDB
Progynon DH	HMDB
Sandrena 1	HMDB
Syndiol	HMDB
Systen	HMDB
Zumenon	HMDB
Estradiol hemihydrate, (17 alpha)-isomer	HMDB
Estradiol, (-)-isomer	HMDB
Estradiol, monosodium salt	HMDB
Estradiol-17 beta	HMDB
17 beta Oestradiol	HMDB
17 beta-Estradiol	HMDB
Estradiol 17 beta	HMDB
Estradiol monohydrate	HMDB
Estradiol orion brand	HMDB
Estradiol, (17-alpha)-isomer	HMDB
Estradiol, sodium salt	HMDB
17 beta Estradiol	HMDB
Estradiol hemihydrate	HMDB
Estradiol, (+-)-isomer	HMDB
Estradiol, (16 alpha,17 alpha)-isomer	HMDB
Estradiol-17 alpha	HMDB
Orion brand OF estradiol	HMDB
17 beta-Oestradiol	HMDB
Estradiol 17 alpha	HMDB
Estradiol 17beta	HMDB
Estradiol anhydrous	HMDB
Estradiol, (16 alpha,17 beta)-isomer	HMDB
Estradiol, (8 alpha,17 beta)-(+-)-isomer	HMDB
Estradiol, (8 alpha,17 beta)-isomer	HMDB
Estradiol, (9 beta,17 alpha)-isomer	HMDB
Estradiol, (9 beta,17 beta)-isomer	HMDB
Novartis pharmaceuticals brand OF estradiol	HMDB
Progynova	HMDB
Estradiol valeriante	HMDB
Estradiol valerate	HMDB
Delestrogen	HMDB
Progynon depot	HMDB
Progynon-depot	HMDB
Estradiol	ChEBI

Chemical Formula

C₁₈H₂₄O₂

Average Mass

272.3820 Da

Monoisotopic Mass

272.17763 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

50-28-2

SMILES

[H]OC1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])[C@@]1([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]21[H]

InChI Identifier

InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

InChI Key

VOXZDWNPVJITMN-ZBRFXRBCSA-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	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, 25 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, 252 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	¹³C NMR Spectrum (1D, 50 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	¹H NMR Spectrum (1D, 300 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, 101 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	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, 600 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	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, 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	¹H NMR Spectrum (1D, 900 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

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
Dalbergia sissoo	LOTUS Database	35616633
Daphnia magna	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Ilybius fenestratus	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Locusta migratoria	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Prunus armeniaca	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Sarcophaga bullata	LOTUS Database	35616633
Solanum glaucophyllum	LOTUS Database	35616633
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
17-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:16469 )
estradiol (CHEBI:16469 )
C18 steroids (estrogens) and derivatives (C00951 )
Estrane and derivatives (C00951 )
Estrogens (C00951 )
C18 steroids (estrogens) and derivatives (LMST02010001 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	178.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0036 mg/mL	Not Available
LogP	4.01	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.75	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	32.12 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

HMDB0000151

DrugBank ID

DB00783

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16469

Good Scents ID

rw1223181

References

General References

Carani C, Qin K, Simoni M, Faustini-Fustini M, Serpente S, Boyd J, Korach KS, Simpson ER: Effect of testosterone and estradiol in a man with aromatase deficiency. N Engl J Med. 1997 Jul 10;337(2):91-5. [PubMed:9211678 ]
Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. [PubMed:11792932 ]
Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. [PubMed:17124377 ]
Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. [PubMed:16487434 ]
Schaap LA, Pluijm SM, Smit JH, van Schoor NM, Visser M, Gooren LJ, Lips P: The association of sex hormone levels with poor mobility, low muscle strength and incidence of falls among older men and women. Clin Endocrinol (Oxf). 2005 Aug;63(2):152-60. [PubMed:16060908 ]
Evagelatou M, Webster AD, Farrant J: Effects of 17 beta-oestradiol on function of lymphocytes from normal donors and patients with common variable immunodeficiency (CVID). Clin Exp Immunol. 1994 Nov;98(2):203-9. [PubMed:7955523 ]
Gibney MJ, Walsh M, Brennan L, Roche HM, German B, van Ommen B: Metabolomics in human nutrition: opportunities and challenges. Am J Clin Nutr. 2005 Sep;82(3):497-503. [PubMed:16155259 ]
Carnevale V, Scillitani A, Vecci E, D'Erasmo E, Romagnoli E, Paglia F, Pepe J, Baldini V, Santori C, De Geronimo S, Minisola S: Dehydroepiandrosterone sulfate and bone resorption rates as reflected by serum levels of C-terminal telopeptide of type I collagen: a study in healthy men. J Endocrinol Invest. 2005 Feb;28(2):102-5. [PubMed:15887853 ]
Jojua T, Sumbadze TS, Papava M: Secretion of sex hormones in patients with open angle glaucoma. Georgian Med News. 2005 Jul-Aug;(124-125):33-7. [PubMed:16148373 ]
Hamden KE, Ford PW, Whitman AG, Dyson OF, Cheng SY, McCubrey JA, Akula SM: Raf-induced vascular endothelial growth factor augments Kaposi's sarcoma-associated herpesvirus infection. J Virol. 2004 Dec;78(23):13381-90. [PubMed:15542692 ]
Lahdes-Vasama TT, Koskimaki JE, Streng TK, Fisch RD, Nilson EA, Santti RS, Tammela TL: Urodynamic findings in men operated on for an undescended testicle. BJU Int. 2003 Dec;92(9):972-6. [PubMed:14632858 ]
Iranmanesh A, Veldhuis JD: Combined inhibition of types I and II 5 alpha-reductase selectively augments the basal (nonpulsatile) mode of testosterone secretion in young men. J Clin Endocrinol Metab. 2005 Jul;90(7):4232-7. Epub 2005 Apr 5. [PubMed:15811930 ]
Stabile LP, Davis AL, Gubish CT, Hopkins TM, Luketich JD, Christie N, Finkelstein S, Siegfried JM: Human non-small cell lung tumors and cells derived from normal lung express both estrogen receptor alpha and beta and show biological responses to estrogen. Cancer Res. 2002 Apr 1;62(7):2141-50. [PubMed:11929836 ]
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Showing NP-Card for Estradiol (NP0001268)

MOL for NP0001268 (Estradiol)

3D MOL for NP0001268 (Estradiol)

3D SDF for NP0001268 (Estradiol)

3D-SDF for NP0001268 (Estradiol)

PDB for NP0001268 (Estradiol)

3D PDB for NP0001268 (Estradiol)

SMILES for NP0001268 (Estradiol)

INCHI for NP0001268 (Estradiol)

Structure for NP0001268 (Estradiol)

3D Structure for NP0001268 (Estradiol)