Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-04-12 17:03:26 UTC |
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Update Date | 2022-03-07 02:49:29 UTC |
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HMDB ID | HMDB0005896 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Hydroxyestradiol |
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Description | 4-Hydroxyestradiol, also known as 3,4,17beta-estriol or 4OHE2, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 4-hydroxyestradiol is considered to be a steroid. Based on a literature review a significant number of articles have been published on 4-Hydroxyestradiol. |
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Structure | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(O)=C3CC[C@@]21[H] InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1 |
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Synonyms | Value | Source |
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3,4,17beta-Estriol | ChEBI | 3,4,17beta-Trihydroxy-1,3,5[10]-estratriene | ChEBI | 4-Hydroxyestradiol-17beta | ChEBI | 4-OH-Estradiol | ChEBI | 4OHE2 | ChEBI | 3,4,17b-Estriol | Generator | 3,4,17Β-estriol | Generator | 3,4,17b-Trihydroxy-1,3,5[10]-estratriene | Generator | 3,4,17Β-trihydroxy-1,3,5[10]-estratriene | Generator | 4-Hydroxyestradiol-17b | Generator | 4-Hydroxyestradiol-17β | Generator | 4-Hydroxyestradiol-17 alpha | HMDB | 4-Hydroxyestradiol-17 beta | HMDB | (17beta)-Estra-1,3,5(10)-triene-3,4,17-triol | HMDB | (17Β)-estra-1,3,5(10)-triene-3,4,17-triol | HMDB | 4-Hydroxy-17beta-estradiol | HMDB | 4-Hydroxy-17β-estradiol | HMDB | Estra-1,3,5(10)-triene-3,4,17beta-triol | HMDB | Estra-1,3,5(10)-triene-3,4,17β-triol | HMDB | 4-Hydroxyestradiol | HMDB |
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Chemical Formula | C18H24O3 |
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Average Molecular Weight | 288.387 |
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Monoisotopic Molecular Weight | 288.172544633 |
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IUPAC Name | (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol |
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Traditional Name | (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol |
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CAS Registry Number | 5976-61-4 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(O)=C3CC[C@@]21[H] |
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InChI Identifier | InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1 |
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InChI Key | QOZFCKXEVSGWGS-ZHIYBZGJSA-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
- 4-hydroxysteroid
- 17-hydroxysteroid
- Hydroxysteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Hydroxyestradiol,1TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O)C(O)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2790.0 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,1TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O)=C4CC[C@H]3[C@@H]1CC[C@@H]2O | 2784.1 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,1TMS,isomer #3 | C[C@]12CC[C@@H]3C4=CC=C(O)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O | 2759.6 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,2TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2800.6 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,2TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2772.7 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,2TMS,isomer #3 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O | 2790.8 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,3TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2802.0 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=C(C=CC(O)=C4O)[C@H]3CC[C@]12C | 3068.6 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12 | 3070.3 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12 | 3040.4 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12 | 3340.5 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12 | 3281.5 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12 | 3292.6 | Semi standard non polar | 33892256 | 4-Hydroxyestradiol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12 | 3479.7 | Semi standard non polar | 33892256 |
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