Estriol 3-glucuronide
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Estriol 3-glucuronide
Estriol 3-glucuronide, or oestriol 3-glucuronide, also known as estriol 3-β-D-glucosiduronic acid, is a natural, steroidal estrogen and a glucuronic acid (β-D-glucopyranuronic acid) conjugate of estriol. It is found in the urine of women as a reversibly formed metabolite of estriol. The positional isomer of estriol 3-glucuronide, estriol 16α-glucuronide, also occurs as an endogenous metabolite of estriol, but to a much greater extent in comparison. See also * Estrogen conjugate * Estradiol glucuronide * Estrone glucuronide * Estradiol sulfate * Estrone sulfate * Lipoidal estradiol * Catechol estrogen A catechol estrogen is a steroidal estrogen that contains catechol (1,2-dihydroxybenzene) within its structure. The catechol estrogens are endogenous metabolites of estradiol and estrone and include the following compounds: * 2-Hydroxylated: ** ... References External links Metabocard for Estradiol 3-Glucuronide - Human Metabolome Database Estriol esters Estrogens ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabolites ...
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Estrone Glucuronide
Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. It has much higher water solubility than does estrone. Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol. When exogenous estradiol is administered orally, it is subject to extensive first-pass metabolism (95%) in the intestines and liver. A single administered dose of estradiol is absorbed 15% as estrone, 25% as estrone sulfate, 25% as estradiol glucuronide, and 25% as estrone glucuronide. Formation of estrogen glucuronide conjugates is particularly important with oral estradiol as the percentage of estrogen glucuronide conjugates in circulation is much higher with oral ingestion than with parenteral estradiol. Estrone glucuronide can be reconverted back into estradiol ...
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Human Metabolites
Humans (''Homo sapiens'') are the most abundant and widespread species of primate, characterized by bipedalism and exceptional cognitive skills due to a large and complex brain. This has enabled the development of advanced tools, culture, and language. Humans are highly social and tend to live in complex social structures composed of many cooperating and competing groups, from families and kinship networks to political states. Social interactions between humans have established a wide variety of values, social norms, and rituals, which bolster human society. Its intelligence and its desire to understand and influence the environment and to explain and manipulate phenomena have motivated humanity's development of science, philosophy, mythology, religion, and other fields of study. Although some scientists equate the term ''humans'' with all members of the genus ''Homo'', in common usage, it generally refers to ''Homo sapiens'', the only extant member. Anatomically mode ...
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Hormones Of The Pregnant Female
A hormone (from the Greek participle , "setting in motion") is a class of signaling molecules in multicellular organisms that are sent to distant organs by complex biological processes to regulate physiology and behavior. Hormones are required for the correct development of animals, plants and fungi. Due to the broad definition of a hormone (as a signaling molecule that exerts its effects far from its site of production), numerous kinds of molecules can be classified as hormones. Among the substances that can be considered hormones, are eicosanoids (e.g. prostaglandins and thromboxanes), steroids (e.g. oestrogen and brassinosteroid), amino acid derivatives (e.g. epinephrine and auxin), protein or peptides (e.g. insulin and CLE peptides), and gases (e.g. ethylene and nitric oxide). Hormones are used to communicate between organs and tissues. In vertebrates, hormones are responsible for regulating a variety of physiological processes and behavioral activities such as digestion, met ...
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Hormones Of The Hypothalamus-pituitary-gonad Axis
A hormone (from the Greek participle , "setting in motion") is a class of signaling molecules in multicellular organisms that are sent to distant organs by complex biological processes to regulate physiology and behavior. Hormones are required for the correct development of animals, plants and fungi. Due to the broad definition of a hormone (as a signaling molecule that exerts its effects far from its site of production), numerous kinds of molecules can be classified as hormones. Among the substances that can be considered hormones, are eicosanoids (e.g. prostaglandins and thromboxanes), steroids (e.g. oestrogen and brassinosteroid), amino acid derivatives (e.g. epinephrine and auxin), protein or peptides (e.g. insulin and CLE peptides), and gases (e.g. ethylene and nitric oxide). Hormones are used to communicate between organs and tissues. In vertebrates, hormones are responsible for regulating a variety of physiological processes and behavioral activities such as digestion, met ...
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Glucuronide Esters
A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. Glucuronidation, the conversion of chemical compounds to glucuronides, is a method that animals use to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. Enzymes that cleave the glycosidic bond of a glucuronide are called glucuronidases. Examples * Miquelianin (Quercetin 3-O-glucuronide) * Morphine-6-glucuronide * Scutellarein-7-glucuronide Scutellarin is a flavone, a type of phenolic chemical compound. It can be found in the plants '' Scutellaria barbata'' and '' S. lateriflora'' which have been used in traditional medicine''.'' T ...
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Estrogens
Estrogen or oestrogen is a category of sex steroid, sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogeny (biology), endogenous estrogens that have estrogenic hormonal activity: estrone (E1), estradiol (E2), and estriol (E3). Estradiol, an estrane, is the most potent and prevalent. Another estrogen called estetrol (E4) is produced only during pregnancy. Estrogens are synthesized in all vertebrates and some insects. Their presence in both vertebrates and insects suggests that estrogenic sex hormones have an ancient evolutionary history. Quantitatively, estrogens circulate at lower levels than androgens in both men and women. While estrogen levels are significantly lower in males than in females, estrogens nevertheless have important physiological roles in males. Like all steroid hormones, estrogens readily diffusion, diffuse across the cell membrane. Once inside the cell, they ...
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Estriol Esters
This is a list of estrogen esters, or ester prodrugs of estrogens. It includes esters, as well as ethers, of steroidal estrogens like estradiol, estrone, and estriol and of nonsteroidal estrogens like the stilbestrols diethylstilbestrol and hexestrol. Esters of steroidal estrogens Estradiol esters Marketed Many esters of estradiol have been marketed, including the following major esters: * Estradiol acetate (Femring, Femtrace, Menoring) * Estradiol benzoate (Agofollin Depot, Progynon-B; Duogynon, Primosiston, Sistocyclin) * Estradiol cypionate (Depo-Estradiol, Depofemin, Estradep; Cyclofem, Lunelle) * Estradiol dipropionate (Agofollin, Di-Ovocyclin, Progynon-DP; EP Hormone Depot) * Estradiol enantate (Perlutal, Topasel, Unalmes, Yectames) * Estradiol undecylate (Delestrec, Progynon Depot) * Estradiol valerate (Delestrogen, Progynon Depot, Progynova; Gravibinon, Mesigyna, Mesygest) * Polyestradiol phosphate (Estradurin) (an estradiol ester in polymeric form) And the follow ...
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Catechol Estrogen
A catechol estrogen is a steroidal estrogen that contains catechol (1,2-dihydroxybenzene) within its structure. The catechol estrogens are endogenous metabolites of estradiol and estrone and include the following compounds: * 2-Hydroxylated: ** 2-Hydroxyestradiol ** 2-Hydroxyestrone ** 2-Hydroxyestriol * 4-Hydroxylated: ** 4-Hydroxyestradiol ** 4-Hydroxyestrone ** 4-Hydroxyestriol The most abundant catechol estrogen in serum and urine is 2-hydroxyestrone, with 2-hydroxyestradiol and 2-hydroxyestriol also being formed, while the principal 4-hydroxy catechol estrogen, 4-hydroxyestrone, is present in only small amounts in urine. 4-Hydroxyestriol has been detected in the urine of pregnant women. The catechol estrogens are formed from estradiol and estrone by cytochrome P450 enzymes predominantly in the liver but also in extrahepatic tissues, and are metabolized by catechol O-methyltransferase (COMT) into methoxylated estrogens such as 2-methoxyestradiol and 4-methoxyestrone as w ...
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Lipoidal Estradiol
Lipoidal estradiol (LE2) is the variety of endogenous C17β long-chain fatty acid esters of estradiol which are formed as metabolites of estradiol. Important examples of these esters include estradiol arachidonate, estradiol lineolate, estradiol oleate, estradiol palmitate, and estradiol stearate. LE2 are estrogens but do not bind to the estrogen receptor, instead acting as prohormones of estradiol. Relative to estradiol, they have far longer-lasting durations of effect due to their much slower rates of metabolism and clearance. It has been hypothesized that LE2 may serve as a store of estrogen for when estradiol levels become low. LE2 are highly lipophilic and hydrophobic and are found in highest concentrations in adipose tissue and other estrogen-sensitive tissues and in low but detectable concentrations in circulation, with none excreted in urine. They have been referred to as the "endogenous counterparts of the synthetic esters of estrogens" like estradiol valerate and estr ...
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Estrone Sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate. In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menopausal hormone therapy; for information on estrone sulfate as a medication, see the estrone sulfate (medication) article. Biological function E1S itself is biologically inactive, with less than 1% of the relative binding affinity of estradiol for the ERα and ERβ. However, it can be transformed by steroid sulfatase, also known as estrogen sulfatase, into estrone, an estrogen. Simultaneously, estrogen sulfotransferases, including SULT1A1 and SULT1E1, convert estrone to E1S, resulting in an equilibrium between the two steroids in various tissues. Estrone can also be converted by 17β-hydroxysteroid dehydrogenases into the more potent estrogen estradiol. E1S levels are much higher than those of estrone and estradiol, and it is thought ...
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Estradiol Sulfate
Estradiol sulfate (E2S), or 17β-estradiol 3-sulfate, is a natural, endogenous steroid and an estrogen ester. E2S itself is biologically inactive, but it can be converted by steroid sulfatase (also called estrogen sulfatase) into estradiol, which is a potent estrogen. Simultaneously, estrogen sulfotransferases convert estradiol to E2S, resulting in an equilibrium between the two steroids in various tissues. Estrone and E2S are the two immediate metabolic sources of estradiol. E2S can also be metabolized into estrone sulfate (E1S), which in turn can be converted into estrone and estradiol. Circulating concentrations of E2S are much lower than those of E1S. High concentrations of E2S are present in breast tissue, and E2S has been implicated in the biology of breast cancer via serving as an active reservoir of estradiol. As the sodium salt, sodium estradiol sulfate, E2S is present as a minor constituent (0.9%) of conjugated equine estrogens (CEEs), or Premarin. It effectively funct ...
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