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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (57)transporters (9) Show 66 proteins XML

enzymes (57)transporters (9) Show 66 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:24 UTC

HMDB ID

HMDB0000151

Secondary Accession Numbers

HMDB0004481
HMDB00151
HMDB04481

Metabolite 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

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

783
  Mrv1652305271900112D          

 23 26  0  0  1  0            999 V2000
    7.5775    1.7429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -1.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5406    0.7074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5406   -0.1176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8262   -0.5300    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1119   -0.1176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3211    0.9588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8262    1.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -0.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119    0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8026    0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395   -1.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5406    1.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -1.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545   -1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5966   -0.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -1.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078   -1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -0.7738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4003   -0.8555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833    0.2124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 13  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 21  1  6  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 22  1  1  0  0  0
  6 10  1  0  0  0  0
  6 14  1  0  0  0  0
  6 23  1  6  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 15  1  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000151

> <DATABASE_NAME>
hmdb

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

> <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                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 783                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      14.145   3.253   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.905  -3.380   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.209   1.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.209  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.876  -0.989   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.542  -0.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.666   1.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.876   2.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.666  -0.689   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.542   1.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.565   0.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.900  -2.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.209   2.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.141  -1.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.518  -3.406   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.128  -2.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.714  -0.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.688  -3.450   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.254  -0.944   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241  -2.615   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      12.340  -1.444   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      11.947  -1.597   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      10.609   0.396   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   20                                                            
CONECT    3    4    7    8   13                                             
CONECT    4    3    5    9   21                                             
CONECT    5    4    6   12   22                                             
CONECT    6    5   10   14   23                                             
CONECT    7    1    3   11                                                  
CONECT    8    3   10                                                       
CONECT    9    4   11                                                       
CONECT   10    6    8                                                       
CONECT   11    7    9                                                       
CONECT   12    5   15                                                       
CONECT   13    3                                                            
CONECT   14    6   16   17                                                  
CONECT   15   12   16                                                       
CONECT   16   14   15   18                                                  
CONECT   17   14   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20    2   18   19                                                  
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    6                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    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 Stereo Labels

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 Molecular Weight

272.382

Monoisotopic Molecular Weight

272.177630012

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][C@@]12CC[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/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

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 )

Ontology

Physiological effect

Health effect

Benign gynecological disease (HMDB: HMDB0000151)
Bleeding (HMDB: HMDB0000151)

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0000151)
Nausea (HMDB: HMDB0000151)

Fibroblast (HMDB: HMDB0000151)

Hematocyte

Platelet (HMDB: HMDB0000151)

Cellular element

Platelet (HMDB: HMDB0000151)

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0000151)

Endoplasmic reticulum (HMDB: HMDB0000151)

Biofluid or Excreta

Cerebrospinal fluid (HMDB: HMDB0000151)

Non-excretory biofluid

Cerebrospinal Fluid (CSF) (PMID: 10585175)
Saliva (PMID: 16155259)
Blood (PMID: 6460495)

Excreta

Urine (PMID: 8478958)

Adrenal cortex (HMDB: HMDB0000151)
Adrenal gland (HMDB: HMDB0000151)

Adrenal Gland (HMDB: HMDB0000151)

Tissue

Connective tissue

Adipose Tissue (HMDB: HMDB0000151)

Epithelium

Epidermis (HMDB: HMDB0000151)

Muscle tissue

Skeletal Muscle (HMDB: HMDB0000151)

Organ substructure

Adrenal Cortex (HMDB: HMDB0000151)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000151)

Source

Endogenous

Endogenous (HMDB: HMDB0000151)

Plant

Plant (HMDB: HMDB0000151)
Fabaceae (HMDB: HMDB0000151)

Exogenous

Food

Food (HMDB: HMDB0000151)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Swine

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

Caprae

Domestic goat (FooDB: FOOD00529)

Equine

Horse (FooDB: FOOD00378)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Pulse

Bean

Common bean (FooDB: FOOD00134)

Process

Role

Physical Properties

State

Solid

Experimental Molecular 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,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	173.336	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000182

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.017	31661259
DarkChem	[M-H]-	163.619	31661259
AllCCS	[M+H]+	168.121	32859911
AllCCS	[M-H]-	174.15	32859911
DeepCCS	[M-2H]-	212.933	30932474
DeepCCS	[M+Na]+	187.798	30932474
AllCCS	[M+H]+	168.1	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	174.0	32859911
AllCCS	[M+HCOO]-	173.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3547.9	Standard polar	33892256
Estradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2655.4	Standard non polar	33892256
Estradiol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2739.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estradiol,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2677.5	Semi standard non polar	33892256
Estradiol,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O	2655.2	Semi standard non polar	33892256
Estradiol,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2708.0	Semi standard non polar	33892256
Estradiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C	2965.7	Semi standard non polar	33892256
Estradiol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12	2953.9	Semi standard non polar	33892256
Estradiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3270.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Estradiol GC-MS (2 TMS)	splash10-017r-1791100000-7b16254894cdcb8ee86d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estradiol EI-B (Non-derivatized)	splash10-00di-1980000000-b2dec84718861de189ec	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estradiol EI-B (Non-derivatized)	splash10-00di-3940000000-f3692a81f624f15d3e0b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estradiol EI-B (Non-derivatized)	splash10-00di-0960000000-be4e96105398cb805cd9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estradiol EI-B (Non-derivatized)	splash10-00di-0790000000-5c858378c15135811824	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estradiol GC-MS (Non-derivatized)	splash10-017r-1791100000-7b16254894cdcb8ee86d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-1490000000-9f16d080d50dcea52de4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (2 TMS) - 70eV, Positive	splash10-0udr-2279400000-cea6d26f1ab9c44b5160	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-075a-2920000000-10218bfa5b56f829853e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol Linear Ion Trap , negative-QTOF	splash10-00di-0490000000-c3c4658cfae36bedff30	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 10V, Negative-QTOF	splash10-00di-0090000000-f73a7a19d55a4f78be01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 40V, Negative-QTOF	splash10-00di-0090000000-f906ca4989738e61667a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 20V, Negative-QTOF	splash10-00di-0090000000-279741ee877c60bb7ab3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-05fr-0590000000-1dd83cbcb3d21edfbdbd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-2900000000-f3279d6cdab9cf3800fd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-8900000000-0efe28378f612aab8c3d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol EI-B (JEOL JMS-01-SG-2) , Positive-QTOF	splash10-00di-1980000000-b2dec84718861de189ec	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol EI-B (HITACHI RMU-6E) , Positive-QTOF	splash10-00di-3940000000-f3692a81f624f15d3e0b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol EI-B (HITACHI M-52) , Positive-QTOF	splash10-00di-0960000000-be4e96105398cb805cd9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol EI-B (HITACHI M-80) , Positive-QTOF	splash10-00di-0790000000-5c83456da6e28375ad51	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-1900000000-51d28e077b0aefa6aa1c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-2900000000-a22a9233ffbb9eb05a1b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol LC-ESI-ITFT , positive-QTOF	splash10-0002-0960000000-d2ee002f4c0363c04e83	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol LC-ESI-ITFT , positive-QTOF	splash10-0002-0960000000-2ad7c6e17386448419df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 80V, Positive-QTOF	splash10-0a4i-2900000000-a22a9233ffbb9eb05a1b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 55V, Positive-QTOF	splash10-0a4i-1900000000-51d28e077b0aefa6aa1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 50V, Positive-QTOF	splash10-002b-0930000000-c177eb564c729479f2be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 30V, Positive-QTOF	splash10-0a4i-0190000000-b572b380a16bb1b20b27	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 35V, Positive-QTOF	splash10-0002-0960000000-d2ee002f4c0363c04e83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 55V, Positive-QTOF	splash10-0002-0960000000-2ad7c6e17386448419df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 40V, Positive-QTOF	splash10-004i-0490000000-ad5217e0b35392226fe0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 20V, Positive-QTOF	splash10-05fr-0090000000-f65d7fb55ed3c4055c71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 30V, Positive-QTOF	splash10-0a4i-0190000000-097099df4d0880cc80a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estradiol 40V, Positive-QTOF	splash10-004i-0490000000-10bda227652deb21fef5	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Brain
Epidermis
Fibroblasts
Kidney
Liver
Neuron
Ovary
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available
Estrone Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000092 uM	Infant (15 days - <1 year old)	Both	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000037 uM	Children (1 - <9 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000176 uM	Children (9 - <11 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000345 uM	Adolescent (11 - <12 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.00004-0.000631 uM	Adolescent (12 - <14 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000936 uM	Adolescent (14 - <19 years old	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000048 uM	Children (1 - <11 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000095 uM	Adolescent (11 - <13 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.000103 uM	Adolescent (13 - <15 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.00014 uM	Adolescent (15 - <19 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.00015 +/- 0.000075 uM	Adult (>18 years old)	Female	Normal	8478958	details
Blood	Detected and Quantified	0.000110 - 0.00130 uM	Adult (>18 years old)	Female	Normal	Molecular You	details
Blood	Detected and Quantified	0 - 0.000220 uM	Adult (>18 years old)	Male	Normal	Molecular You	details
Blood	Detected and Quantified	0.00009 (0.0-0.00018) uM	Adult (>18 years old)	Male	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	0.00009 (0.0-0.00018) uM	Adult (>18 years old)	Female	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	0.000099-0.000749 uM	Adult (>18 years old)	Not Specified	Normal	7477119	details
Blood	Detected and Quantified	<0.000206 uM	Not Specified	Male	Normal	16477341	details
Blood	Detected and Quantified	0.0000477+/- 0.00008 uM	Children (1-13 years old)	Both	Normal	26079780	details
Blood	Detected and Quantified	0.000184-0.00177 uM	Adult (>18 years old)	Female	Normal	26161337	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0000011 +/- 0.0000003 uM	Adult (>18 years old)	Female	Normal	10585175	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0000007 - 0.000011 uM	Adult (>18 years old)	Female	Normal	10585175	details
Saliva	Detected and Quantified	0.000018 +/- 0.000006 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000016 +/- 0.000005 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000019 +/- 0.000007 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000014 +/- 0.000005 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000009 +/- 0.000004 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000014 +/- 0.000007 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000012 +/- 0.000006 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000007 +/- 0.000004 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000013 +/- 0.000006 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	<1.00 uM	Adult (>18 years old)	Both	Normal	16155259	details
Urine	Detected and Quantified	0.00059 +/- 0.00025 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8478958	details
Urine	Detected and Quantified	0.0011 +/- 0.00061 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	12707870	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000095 +/- 0.000036 uM	Adult (>18 years old)	Male	Severe coronary artery disease	6460495	details
Blood	Detected and Quantified	0.00011 +/- 0.00005 uM	Adult (>18 years old)	Male	Minor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms	6460495	details
Blood	Detected and Quantified	0.000099 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected and Quantified	0.00039 (0.000037-0.00073) uM	Adult (>18 years old)	Female	Menstrual cycle	The Merck Manual,...	details
Blood	Detected and Quantified	0.00092 (0.00037-0.0015) uM	Adult (>18 years old)	Female	Menstrual cycle	The Merck Manual,...	details
Blood	Detected and Quantified	0.00050 (0.000055-0.00095) uM	Adult (>18 years old)	Female	Menstrual cycle	The Merck Manual,...	details
Blood	Detected and Quantified	<0.000005 uM	Children (1-13 years old)	Female	Aromatase deficiency	9177373	details
Blood	Detected and Quantified	<0.0000734 uM	Adolescent (13-18 years old)	Female	Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency	16477341	details
Blood	Detected and Quantified	0.000037-0.000141 uM	Adult (>18 years old)	Male	X-linked ichthyosis	3864567	details
Blood	Detected and Quantified	0-0.000201 uM	Children (1-13 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	0.000099 uM	Adult (>18 years old)	Female	Proprotein Convertase 1/3 Deficiency	7477119	details
Blood	Detected and Quantified	0.000062 +/- 0.0000844 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.0000294 +/- 0.000088 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.000055 uM	Adolescent (13-18 years old)	Female	Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency	26161337	details
Blood	Detected and Quantified	0.000114 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency	26161337	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000006 (0.0000007-0.000011) uM	Adult (>18 years old)	Female	Gynecological diseases (benign)	10585175	details
Urine	Detected and Quantified	0.0016 +/- 0.0011 umol/mmol creatinine	Adult (>18 years old)	Female	Stress urinary incontinence	12707870	details

Associated Disorders and Diseases

Disease References

Menstrual cycle
(). The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.. .
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ] Benkert AR, Young M, Robinson D, Hendrickson C, Lee PA, Strauss KA: Severe Salt-Losing 3beta-Hydroxysteroid Dehydrogenase Deficiency: Treatment and Outcomes of HSD3B2 c.35G>A Homozygotes. J Clin Endocrinol Metab. 2015 Aug;100(8):E1105-15. doi: 10.1210/jc.2015-2098. Epub 2015 Jun 16. [PubMed:26079780 ]
Aromatase deficiency
Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
Congenital Adrenal Hyperplasia, due to 17-Hydroxylase-Deficiency
Wong SL, Shu SG, Tsai CR: Seventeen alpha-hydroxylase deficiency. J Formos Med Assoc. 2006 Feb;105(2):177-81. doi: 10.1016/S0929-6646(09)60342-9. [PubMed:16477341 ] Kim SM, Rhee JH: A case of 17 alpha-hydroxylase deficiency. Clin Exp Reprod Med. 2015 Jun;42(2):72-6. doi: 10.5653/cerm.2015.42.2.72. Epub 2015 Jun 30. [PubMed:26161337 ]
X-linked ichthyosis
Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Lipoid Congenital Adrenal Hyperplasia
Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]
Proprotein Convertase 1/3 Deficiency
O'Rahilly S, Gray H, Humphreys PJ, Krook A, Polonsky KS, White A, Gibson S, Taylor K, Carr C: Brief report: impaired processing of prohormones associated with abnormalities of glucose homeostasis and adrenal function. N Engl J Med. 1995 Nov 23;333(21):1386-90. doi: 10.1056/NEJM199511233332104. [PubMed:7477119 ]
Benign gynecological diseases
Murakami K, Nakagawa T, Shozu M, Uchide K, Koike K, Inoue M: Changes with aging of steroidal levels in the cerebrospinal fluid of women. Maturitas. 1999 Sep 24;33(1):71-80. [PubMed:10585175 ]

Associated OMIM IDs

201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
613546 (Aromatase deficiency)
202110 (Congenital Adrenal Hyperplasia, due to 17-Hydroxylase-Deficiency)
308100 (X-linked ichthyosis)
201710 (Lipoid Congenital Adrenal Hyperplasia)
600955 (Proprotein Convertase 1/3 Deficiency)

External Links

DrugBank ID

DB00783

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000362

KNApSAcK ID

Not Available

Chemspider ID

5554

KEGG Compound ID

C00951

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16469

Food Biomarker Ontology

Not Available

VMH ID

ESTRADIOL

MarkerDB ID

MDB00000072

Good Scents ID

Not Available

References

Synthesis Reference

Vasiljeva, L. L.; Demin, P. M.; Kochev, D. M.; Lapitskaya, M. A.; Pivnitskya, K. K. New synthesis of estradiol from androsta-1,4-diene-3,17-dione. Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1999), 48(3), 593-595.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Chabbert-Buffet N, Bouchard P: [Physiology and exploration of the gonadotropic axis]. Rev Prat. 1999 Jun 15;49(12):1270-6. [PubMed:10488657 ]
Schonknecht P, Henze M, Hunt A, Klinga K, Haberkorn U, Schroder J: Hippocampal glucose metabolism is associated with cerebrospinal fluid estrogen levels in postmenopausal women with Alzheimer's disease. Psychiatry Res. 2003 Oct 30;124(2):125-7. [PubMed:14561431 ]
Elliott KJ, Cable NT, Reilly T: Does oral contraceptive use affect maximum force production in women? Br J Sports Med. 2005 Jan;39(1):15-9. [PubMed:15618333 ]
Blomquist CH, D'Ascoli PT: Gestational development of human placental 17 beta-hydroxysteroid oxidoreductase types 1 and 2. Hum Reprod. 1995 Oct;10(10):2685-9. [PubMed:8567793 ]
Fraser D, Padwick ML, Whitehead M, Coffer A, King RJ: Presence of an oestradiol receptor-related protein in the skin: changes during the normal menstrual cycle. Br J Obstet Gynaecol. 1991 Dec;98(12):1277-82. [PubMed:1777462 ]
Greb RR, Grieshaber K, Gromoll J, Sonntag B, Nieschlag E, Kiesel L, Simoni M: A common single nucleotide polymorphism in exon 10 of the human follicle stimulating hormone receptor is a major determinant of length and hormonal dynamics of the menstrual cycle. J Clin Endocrinol Metab. 2005 Aug;90(8):4866-72. Epub 2005 May 10. [PubMed:15886248 ]
Archer JS, Love-Geffen TE, Herbst-Damm KL, Swinney DA, Chang JR: Effect of estradiol versus estradiol and testosterone on brain-activation patterns in postmenopausal women. Menopause. 2006 May-Jun;13(3):528-37. [PubMed:16735951 ]
Anwar A, McTernan PG, Anderson LA, Askaa J, Moody CG, Barnett AH, Eggo MC, Kumar S: Site-specific regulation of oestrogen receptor-alpha and -beta by oestradiol in human adipose tissue. Diabetes Obes Metab. 2001 Oct;3(5):338-49. [PubMed:11703424 ]
Tanko LB, Christiansen C: Effects of 17beta-oestradiol plus different doses of drospirenone on adipose tissue, adiponectin and atherogenic metabolites in postmenopausal women. J Intern Med. 2005 Dec;258(6):544-53. [PubMed:16313478 ]
Sulcova J, Hampl R, Hill M, Starka L, Novacek A: Delayed effects of short-term transdermal application of 7-oxo-dehydroepiandrosterone on its metabolites, some hormonal steroids and relevant proteohormones in healthy male volunteers. Clin Chem Lab Med. 2005;43(2):221-7. [PubMed:15843221 ]
Shimizu I, Kohno N, Tamaki K, Shono M, Huang HW, He JH, Yao DF: Female hepatology: favorable role of estrogen in chronic liver disease with hepatitis B virus infection. World J Gastroenterol. 2007 Aug 28;13(32):4295-305. [PubMed:17708600 ]
Friedman AE: Can a single model explain both breast cancer and prostate cancer? Theor Biol Med Model. 2007 Aug 1;4:28. [PubMed:17678531 ]
Ishii H, Tsurugizawa T, Ogiue-Ikeda M, Asashima M, Mukai H, Murakami G, Hojo Y, Kimoto T, Kawato S: Local production of sex hormones and their modulation of hippocampal synaptic plasticity. Neuroscientist. 2007 Aug;13(4):323-34. [PubMed:17644764 ]
Behl C, Widmann M, Trapp T, Holsboer F: 17-beta estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochem Biophys Res Commun. 1995 Nov 13;216(2):473-82. [PubMed:7488136 ]
Sharpe RM, Skakkebaek NE: Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;341(8857):1392-5. [PubMed:8098802 ]
Pentikainen V, Erkkila K, Suomalainen L, Parvinen M, Dunkel L: Estradiol acts as a germ cell survival factor in the human testis in vitro. J Clin Endocrinol Metab. 2000 May;85(5):2057-67. [PubMed:10843196 ]
Schmidt JW, Wollner D, Curcio J, Riedlinger J, Kim LS: Hormone replacement therapy in menopausal women: Past problems and future possibilities. Gynecol Endocrinol. 2006 Oct;22(10):564-77. [PubMed:17135036 ]
Foresta C, Zuccarello D, Biagioli A, De Toni L, Prana E, Nicoletti V, Ambrosini G, Ferlin A: Oestrogen stimulates endothelial progenitor cells via oestrogen receptor-alpha. Clin Endocrinol (Oxf). 2007 Oct;67(4):520-5. Epub 2007 Jun 15. [PubMed:17573901 ]

Only showing the first 10 proteins. There are 66 proteins in total.

Show all enzymes and transporters

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

Estradiol + NAD(P)(+) → Estrone + NAD(P)H	details
Estradiol + NAD → Estrone + NADH + Hydrogen Ion	details
Estradiol + NADP → Estrone + NADPH + Hydrogen Ion	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

3. Estrogen receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular weight:: 59215.8

References

Vijayanathan V, Greenfield NJ, Thomas TJ, Ivanova MM, Tyulmenkov VV, Klinge CM, Gallo MA, Thomas T: Effects of estradiol and 4-hydroxytamoxifen on the conformation, thermal stability, and DNA recognition of estrogen receptor beta. Biochem Cell Biol. 2007 Feb;85(1):1-10. [PubMed:17464340 ]
Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412 ]

Enzyme Details

4. 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

Estradiol + NAD(P)(+) → Estrone + NAD(P)H	details
Estradiol + NAD → Estrone + NADH + Hydrogen Ion	details
Estradiol + NADP → Estrone + NADPH + Hydrogen Ion	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

Estradiol + Uridine diphosphate glucuronic acid → 17-beta-Estradiol-3-glucuronide + Uridine 5'-diphosphate	details

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Tamai I, Nozawa T, Koshida M, Nezu J, Sai Y, Tsuji A: Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. Pharm Res. 2001 Sep;18(9):1262-9. [PubMed:11683238 ]

Enzyme Details

2. Solute carrier organic anion transporter family member 2B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:: SLCO2B1
Uniprot ID:: O94956
Molecular weight:: 76697.9

References

Tamai I, Nozawa T, Koshida M, Nezu J, Sai Y, Tsuji A: Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. Pharm Res. 2001 Sep;18(9):1262-9. [PubMed:11683238 ]

Enzyme Details

3. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405 ]
Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871 ]

Enzyme Details

4. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Imai Y, Asada S, Tsukahara S, Ishikawa E, Tsuruo T, Sugimoto Y: Breast cancer resistance protein exports sulfated estrogens but not free estrogens. Mol Pharmacol. 2003 Sep;64(3):610-8. [PubMed:12920197 ]
Imai Y, Tsukahara S, Ishikawa E, Tsuruo T, Sugimoto Y: Estrone and 17beta-estradiol reverse breast cancer resistance protein-mediated multidrug resistance. Jpn J Cancer Res. 2002 Mar;93(3):231-5. [PubMed:11927002 ]

Enzyme Details

5. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [PubMed:10660625 ]

Enzyme Details

6. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894 ]
Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566 ]

Enzyme Details

8. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]

Enzyme Details

9. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]

Only showing the first 10 proteins. There are 66 proteins in total.

Show all enzymes and transporters

Showing metabocard for Estradiol (HMDB0000151)

MOL for HMDB0000151 (Estradiol)

3D MOL for HMDB0000151 (Estradiol)

3D SDF for HMDB0000151 (Estradiol)

3D-SDF for HMDB0000151 (Estradiol)

PDB for HMDB0000151 (Estradiol)

3D PDB for HMDB0000151 (Estradiol)

SMILES for HMDB0000151 (Estradiol)

INCHI for HMDB0000151 (Estradiol)

Structure for HMDB0000151 (Estradiol)

3D Structure for HMDB0000151 (Estradiol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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