Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:04 UTC |
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HMDB ID | HMDB0000338 |
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Secondary Accession Numbers | - HMDB0003962
- HMDB00338
- HMDB03962
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Metabolite Identification |
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Common Name | 2-Hydroxyestradiol |
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Description | 2-Hydroxyestradiol is generated from estradiol by a Cytochrome P450. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. It inhbits catechol-O-methyltransferase (COMT) activity. Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neutransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688 ). |
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Structure | |
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Synonyms | Value | Source |
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(17beta)-Estra-1,3,5(10)-triene-2,3,17-triol | ChEBI | 2-Hydroxyestradiol-17beta | ChEBI | 2-OH-e2 | ChEBI | 2-OH-Estradiol | ChEBI | (17b)-Estra-1,3,5(10)-triene-2,3,17-triol | Generator | (17Β)-estra-1,3,5(10)-triene-2,3,17-triol | Generator | 2-Hydroxyestradiol-17b | Generator | 2-Hydroxyestradiol-17β | Generator | (17b)-Estra-1,3, 5(10)-triene-2,3,17-triol | HMDB | (17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triol | HMDB | 1,3,5(10)-Estratriene-2,3,17Beta-triol | HMDB | 17beta-2-Hydroxyestradiol | HMDB | 2,3,17b-Trihydroxyestra-1,3,5(10)-triene | HMDB | 2-Hydroxy-17beta-estradiol | HMDB | 2-Hydroxy-estradiol | HMDB | ECS | HMDB | Estra-1,3,5 (10)-triene-2,3,17.beta.-triol | HMDB | Estra-1,3,5(10)-triene-2,3,17-beta-triol | HMDB | Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0) | HMDB | Estra-1,3,5(10)-triene-2,3,17b-triol | HMDB | Estra-1,3,5(10)-triene-2,3,17beta-triol | HMDB | 2-Hydroxyestradiol-17 alpha | HMDB | 2-Hydroxyestradiol-17 beta | HMDB | 2-Hydroxyestradiol, (17alpha)-isomer | HMDB | 2-Hydroxyestradiol, 4-(14)C-labeled | HMDB |
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Chemical Formula | C18H24O3 |
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Average Molecular Weight | 288.3814 |
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Monoisotopic Molecular Weight | 288.172544634 |
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IUPAC Name | (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol |
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Traditional Name | (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol |
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CAS Registry Number | 362-05-0 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3 |
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InChI Identifier | InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1 |
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InChI Key | DILDHNKDVHLEQB-XSSYPUMDSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Estrane steroids |
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Direct Parent | Estrogens and derivatives |
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Alternative Parents | |
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Substituents | - Estrogen-skeleton
- 3-hydroxysteroid
- 2-hydroxysteroid
- Hydroxysteroid
- 17-hydroxysteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 190 - 191 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adr-2490000000-7e8a9e3990faceb5f6d0 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-002u-1002900000-79ac7707883246949511 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00ei-2950000000-326e2d3fee4fb8b3ca6c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-2910000000-553a7988f4c2019ec5d5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0f96-8975000000-eef1fcf44ed6a27f53a9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dr-0190000000-0e1c17e32d9c1e4063eb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dr-0790000000-01416dcd9eea3747d3c5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-6970000000-d27a7add654c423ec534 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-805faf5743eec20547cb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-c39e06f8fdeeb111e97f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-1190000000-36538cb7b1a03d7b2ff7 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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General References | - Takanashi K, Honma T, Kashiwagi T, Honjo H, Yoshizawa I: Detection and measurement of urinary 2-hydroxyestradiol 17-sulfate, a potential placental antioxidant during pregnancy. Clin Chem. 2000 Mar;46(3):373-8. [PubMed:10702524 ]
- Elce JS, Bird CE, Chandra J: Water-soluble products of the estrogens. Bile metabolites of 2-hydroxyestradiol-17beta in man. J Clin Endocrinol Metab. 1973 May;36(5):1027-30. [PubMed:4698236 ]
- Zhu BT, Conney AH: Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 1998 Jan;19(1):1-27. [PubMed:9472688 ]
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