Estriol-16-Glucuronide (BioDeep_00000003072)

 

Secondary id: BioDeep_00000405647, BioDeep_00000638201

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6R)-6-[[(8R,9S,13S,14S,16R,17R)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

化学式: C24H32O9 (464.2046222)
中文名称: 雌三醇-16beta-D-葡糖苷酸
谱图信息: 最多检出来源 Homo sapiens(urine) 0.35%

分子结构信息

SMILES: CC12CCC3C(C1CC(C2O)OC4C(C(C(C(O4)C(=O)O)O)O)O)CCC5=C3C=CC(=C5)O
InChI: InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(21(24)29)32-23-19(28)17(26)18(27)20(33-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1

描述信息

Estriol-16-glucuronide is a glucuronide derivative of the steroid estriol where the glucuronic acid is attached to the 16-hydroxyl group of Estriol. Glucuronidation is used 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. Estriol (also known as oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta. [HMDB]
Estriol-16-glucuronide is a glucuronide derivative of the steroid estriol where the glucuronic acid is attached to the 16-hydroxyl group of Estriol. Glucuronidation is used 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. Estriol (also known as oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

34 个代谢物同义名

(2S,3S,4S,5R,6R)-6-[[(8R,9S,13S,14S,16R,17R)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid; 3,17 beta-Dihydroxy-1,3,5(10)-estratrien-16 alpha-yl-beta-D-glucopyranosiduronic acid; estra-1,3,5(10)-triene-3,16alpha,17beta-triol 16-D-glucuronide; 16α,17β-Estriol 16-(β-δ-glucuronide); Estra-1,3,5(10)-triene-3,16a,17b-triol 16-D-glucuronide; Estriol-16-(beta-D-glucuronide), (16beta,17beta)-isomer; Estra-1,3,5(10)-triene-3,16α,17β-triol 16-D-glucuronide; 16α,17β-Estriol 16-(β-D-glucuronide); 16alpha,17beta-Estriol 16-(beta-delta-glucuronide); Estriol-16 alpha-(beta-D-glucuronide), sodium salt; 16alpha,17beta-Estriol 16-O-(beta-D-glucuronide); 16alpha,17beta-Estriol 16-(beta-D-glucuronide); Estriol-16beta-D-glucopyranosiduronic acid; Estriol 16α-(β-D-glucuronide); 16Α,17β-estriol 16-O-(β-D-glucuronide); 16a,17b-Estriol 16-O-(b-D-glucuronide); Estriol-16 alpha-(beta-D-glucuronide); 16Α,17β-estriol 16-(β-D-glucuronide); 16a,17b-Estriol 16-(b-D-glucuronide); Estriol 16alpha-(beta-D-glucuronide); Estriol-16-glucosiduronic acid; Estriol-16 alpha-glucuronide; Oestriol-16alpha-glucuronide; Estriol-16alpha-glucuronide; Estriol-16-glucosiduronate; Oestriol-16a-glucuronide; Oestriol-16α-glucuronide; Estriol-16α-glucuronide; Estriol-16a-glucuronide; Estriol-16-Glucuronide; 16-Glucuronide-estriol; NSC93823; 16-Glucuronide-estriol



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Yoon Jung Yang, Jeongae Lee, Man Ho Choi, Bong Chul Chung. Direct determination of estriol 3- and 16-glucuronides in pregnancy urine by column-switching liquid chromatography with electrospray tandem mass spectrometry. Biomedical chromatography : BMC. 2003 Jun; 17(4):219-25. doi: 10.1002/bmc.215. [PMID: 12833386]
  • Zhe-Sheng Chen, Elizabeth Hopper-Borge, Martin G Belinsky, Irina Shchaveleva, Elena Kotova, Gary D Kruh. Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Molecular pharmacology. 2003 Feb; 63(2):351-8. doi: 10.1124/mol.63.2.351. [PMID: 12527806]
  • T Iwata, T Hirose, M Yamaguchi. Direct determination of estriol 3- and 16-glucuronides in pregnancy urine by column-switching high-performance liquid chromatography with fluorescence detection. Journal of chromatography. B, Biomedical sciences and applications. 1997 Aug; 695(2):201-7. doi: 10.1016/s0378-4347(97)00194-1. [PMID: 9300855]
  • U Tiel, P Heilmann, R Rejaibi, M Schöneshöfer. Urinary oestriol-16-glucuronide determined by "on-line" liquid chromatography. Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie. 1989 Apr; 27(4):205-9. doi: 10.1515/cclm.1989.27.4.205. [PMID: 2544654]
  • S Z Cekan, M S Beksac, E Wang, S Shi, B Masironi, B M Landgren, E Diczfalusy. The prediction and/or detection of ovulation by means of urinary steroid assays. Contraception. 1986 Apr; 33(4):327-45. doi: 10.1016/0010-7824(86)90095-8. [PMID: 3731775]
  • F Andreolini, C Borra, F Caccamo, A Di Corcia, I Nicoletti, R Samperi, F Improta. Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clinical chemistry. 1985 Oct; 31(10):1698-702. doi: . [PMID: 2994907]
  • F Andreolini, C Borra, A Di Corcia, R Samperi, G Raponi. Improved determination of estriol-16 alpha-glucuronide in pregnancy urine by direct liquid chromatography with fluorescence detection. Clinical chemistry. 1985 Jan; 31(1):124-6. doi: 10.1093/clinchem/31.1.124. [PMID: 3965188]
  • H H Kay, J C Hobbins. Correlation of amniotic fluid estrogens with L/S ratios and urinary estriols. The Journal of reproductive medicine. 1984 Apr; 29(4):222-6. doi: NULL. [PMID: 6716365]
  • H Okada, H Honjo, J Yasuda, K Otsubo, K Omori, K Tsukamoto, T Yamamoto, M Numazawa, T Nambara. Estradiol-17 beta and estradiol-17-glucosiduronate before and at delivery. Biological research in pregnancy and perinatology. 1984; 5(2):68-73. doi: . [PMID: 6743734]
  • T Takami, T Tezuka, H Manita, A Kambegawa. [A simple method for radioimmunoassay of total estrogen in urine]. Nihon Naibunpi Gakkai zasshi. 1983 Jan; 59(1):10-9. doi: 10.1507/endocrine1927.59.1_10. [PMID: 6299812]
  • K L Cheesman, Ben-Nun, R T Chatterton, M R Cohen. Relationship of luteinizing hormone, pregnanediol-3-glucuronide, and estriol-16-glucuronide in urine of infertile women with endometriosis. Fertility and sterility. 1982 Nov; 38(5):542-8. doi: 10.1016/s0015-0282(16)46632-x. [PMID: 7128839]
  • K Shimada, F Xie, T Nambara. Studies on steroids. CLXXIX. Determination of estriol 16- and 17-glucuronide in biological fluids by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1982 Oct; 232(1):13-8. doi: NULL. [PMID: 7142322]
  • K Omori. [Dynamics of estriol-16-glucosiduronate (E3-16-G) in early pregnancy -- its prognostic value in complicated pregnancy (author's transl)]. Nihon Naibunpi Gakkai zasshi. 1982 May; 58(5):689-705. doi: 10.1507/endocrine1927.58.5_689. [PMID: 7106323]
  • T Nambara, K Shimada, T Ohkubo, T Niwa. Preparation and antigenic properties of estriol 16-glucuronide- and estradiol 17-glucuronide-[C-6]-bovine serum albumin conjugates. Journal of steroid biochemistry. 1982 Apr; 16(4):533-8. doi: 10.1016/0022-4731(82)90075-9. [PMID: 7087478]
  • C M Branch, P O Collins, W P Collins. Ovulation prediction: changes in the concentrations of urinary estrone-3-glucuronide, estradiol-17 beta-glucuronide and estriol-16 alpha-glucuronide during conceptional cycles. Journal of steroid biochemistry. 1982 Feb; 16(2):345-7. doi: 10.1016/0022-4731(82)90189-3. [PMID: 7078170]
  • A R MacLean, K H Outch, J M Russell, J B Brown, P M Dennis. Monitoring induction of ovulation by rapid radioimmunoassays of oestrogen and pregnanediol glucuronides. Annals of clinical biochemistry. 1981 Nov; 18(Pt 6):343-9. doi: 10.1177/000456328101800604. [PMID: 7316453]
  • K Musch, A S Wolf, C Lauritzen. [Comparison of two methods for the determination of oestrogens in pregnancy urine (author's transl)]. Zeitschrift fur Geburtshilfe und Perinatologie. 1981 Oct; 185(5):284-7. doi: NULL. [PMID: 7198339]
  • G Barnard, W P Collins, F Kohen, H R Lindner. The measurement of urinary estriol-16 alpha-glucuronide by a solid-phase chemiluminescence immunoassay. Journal of steroid biochemistry. 1981 Sep; 14(9):941-8. doi: 10.1016/0022-4731(81)90244-2. [PMID: 7300359]
  • I Schiff, D Tulchinsky, K J Ryan, S Kadner, M Levitz. Plasma estriol and its conjugates following oral and vaginal administration of estriol to postmenopausal women: correlations with gonadotropin levels. American journal of obstetrics and gynecology. 1980 Dec; 138(8):1137-41. doi: 10.1016/s0002-9378(16)32780-6. [PMID: 6778214]
  • P Samarajeewa, S Leepipatpaiboon, W F Coulson. The isolation of estriol-16 alpha-glucuronide and pregnanediol-3 alpha-glucuronide from late pregnancy urine. Steroids. 1980 Nov; 36(5):611-8. doi: 10.1016/0039-128x(80)90083-5. [PMID: 7456104]
  • F Kohen, J B Kim, G Barnard, H R Lindner. An assay for urinary estriol-16 alpha-glucuronide based on antibody-enhanced chemiluminescence. Steroids. 1980 Oct; 36(4):405-19. doi: 10.1016/0039-128x(80)90029-x. [PMID: 7444992]
  • F Z Stanczyk, I Miyakawa, U Goebelsmann. Direct radioimmunoassay of urinary estrogen and pregnanediol glucuronides during the menstrual cycle. American journal of obstetrics and gynecology. 1980 Jun; 137(4):443-50. doi: 10.1016/0002-9378(80)91125-4. [PMID: 7386528]
  • T S Baker, K Jennison, A E Kellie. A possible method for the detection of ovulation and the determination of the duration of the fertile period. Journal of steroid biochemistry. 1980 Jan; 12(?):411-5. doi: 10.1016/0022-4731(80)90300-3. [PMID: 7421226]