16a-Hydroxydehydroisoandrosterone (BioDeep_00000002634)

Main id: BioDeep_00000016688

 

human metabolite Endogenous blood metabolite


代谢物信息卡片


(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

化学式: C19H28O3 (304.2038338)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC12CCC(CC1=CCC3C2CCC4(C3CC(C4=O)O)C)O
InChI: InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3

描述信息

16a-Hydroxydehydroisoandrosterone is a metabolite present during pregnancy with increased concentrations as it progresses (PMID 6461703). A reduced level of 16a-Hydroxydehydroisoandrosterone is observed in cases of Placental sulfatase deficiency (PSD), a rare disorder with low estrogen production due to placental enzymatic deficiency. (PMID 2150812) [HMDB]
16a-Hydroxydehydroisoandrosterone is a metabolite present during pregnancy with increased concentrations as it progresses (PMID 6461703). A reduced level of 16a-Hydroxydehydroisoandrosterone is observed in cases of Placental sulfatase deficiency (PSD), a rare disorder with low estrogen production due to placental enzymatic deficiency. (PMID 2150812).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

29 个代谢物同义名

(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one; 16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomer; 16-Hydroxydehydroepiandrosterone, (16beta)-isomer; 3 beta,16 alpha-Dihydroxyandrost-5-en-17-one; 3 beta,16 beta-Dihydroxyandrost-5-en-17-one; 3beta,16alpha-Dihydroxy-androst-5-en-17-one; 3beta,16alpha-Dihydroxyandrost-5-en-17-one; 16 alpha-Hydroxy-dehydroepiandrosterone; 16alpha-Hydroxy-dehydroepiandrosterone; 5-Androstene-3beta,16alpha-diol-17-one; 16 alpha-Hydroxydehydroisoandrosterone; 16alpha-Hydroxydehydroisoandrosterone; 16alpha-Hydroxydehydroepiandrosterone; 16 beta-Hydroxydehydroepiandrosterone; 3b,16a-Dihydroxy-androst-5-en-17-one; 3Β,16α-dihydroxy-androst-5-en-17-one; 3b,16a-Dihydroxyandrost-5-en-17-one; 3,16-Dihydroxyandrost-5-en-17-one; 16Α-hydroxydehydroisoandrosterone; 16Α-hydroxydehydroepiandrosterone; 16a-Hydroxydehydroepiandrosterone; 16a-Hydroxydehydroisoandrosterone; Androst-5-ene-3b-16a-diol-17-one; 16-Hydroxydehydroepiandrosterone; 5-Androstene-3b,16a-diol-17-one; 5-Androstene-3β,16α-diol-17-one; 16a-Hydroxydehydroandrosterone; 16-Hydroxydehydroandrosterone; 16a-Hydroxy-dhea



数据库引用编号

15 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)

3 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

  • Donna Elizabeth Sunny, Elke Hammer, Till Ittermann, Elisabeth Luise Krüger, Stephanie Hübner, Michaela Friederike Hartmann, Stefan Alexander Wudy, Uwe Völker, Matthias Heckmann. Fetal Zone Steroids and Estrogen Show Sex Specific Effects on Oligodendrocyte Precursor Cells in Response to Oxidative Damage. International journal of molecular sciences. 2021 Jun; 22(12):. doi: 10.3390/ijms22126586. [PMID: 34205405]
  • Yuyong Ke, Renaud Gonthier, Fernand Labrie. The conversion of 16β hydroxyldehydroepiandrosterone in human serum. Steroids. 2016 May; 109(?):50-5. doi: 10.1016/j.steroids.2016.02.007. [PMID: 26896786]
  • Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
  • Pieter Van Renterghem, Peter Van Eenoo, Pierre-Edouard Sottas, Martial Saugy, Frans Delbeke. Subject-based steroid profiling and the determination of novel biomarkers for DHT and DHEA misuse in sports. Drug testing and analysis. 2010 Nov; 2(11-12):582-8. doi: 10.1002/dta.206. [PMID: 21204290]
  • Jakub Hert, Martin Hill, Richard Hampl. Gas chromatographic-mass spectrometric identification of 16alpha-hydroxy-dehydroepiandrosterone in human seminal plasma. Steroids. 2004 Oct; 69(11-12):773-7. doi: 10.1016/j.steroids.2004.05.017. [PMID: 15579330]
  • I A Glass, R C Lam, T Chang, E Roitman, L J Shapiro, C H Shackleton. Steroid sulphatase deficiency is the major cause of extremely low oestriol production at mid-pregnancy: a urinary steroid assay for the discrimination of steroid sulphatase deficiency from other causes. Prenatal diagnosis. 1998 Aug; 18(8):789-800. doi: . [PMID: 9742566]
  • N Tagawa, S Kusuda, Y Kobayashi. C16 hydroxylation of 3beta-hydroxy-delta5-steroids during the early neonatal period. Biological & pharmaceutical bulletin. 1997 Dec; 20(12):1295-9. doi: 10.1248/bpb.20.1295. [PMID: 9448107]
  • K Hirato, T Yanaihara. Serum steroid hormone levels in neonates born from the mother with placental sulfatase deficiency. Endocrinologia japonica. 1990 Oct; 37(5):731-9. doi: 10.1507/endocrj1954.37.731. [PMID: 2150812]
  • E A Zbella, J Ilekis, A Scommegna, R Benveniste. Competitive studies with dehydroepiandrosterone sulfate and 16 alpha-hydroxydehydroepiandrosterone sulfate in cultured human choriocarcinoma JEG-3 cells: effect on estrone, 17 beta-estradiol, and estriol secretion. The Journal of clinical endocrinology and metabolism. 1986 Sep; 63(3):751-7. doi: 10.1210/jcem-63-3-751. [PMID: 2942557]
  • T Akiyama, M Hashino, E Kawamura, T Kosaki, T Yanaihara, T Nakayama, H Mori. [Determination of serum 16 alpha-hydroxydehydroepiandrosterone, 16 alpha-hydroxyestrone and estriol by gas chromatography-mass spectrometry and their perinatal movement]. Nihon Sanka Fujinka Gakkai zasshi. 1986 Apr; 38(4):505-12. doi: . [PMID: 2939158]
  • G Lykkesfeldt, M D Nielsen, A E Lykkesfeldt. Placental steroid sulfatase deficiency: biochemical diagnosis and clinical review. Obstetrics and gynecology. 1984 Jul; 64(1):49-54. doi: . [PMID: 6234482]
  • Y Gothoda, K Hirato, T Yanaihara, T Nakayama, A Kanbegawa. [A study of 16 alpha OH-DHA and 16 alpha OH-pregnenolone in feto-placental unit (author's transl)]. Nihon Sanka Fujinka Gakkai zasshi. 1982 Mar; 34(3):325-34. doi: . [PMID: 6461703]
  • S Kojima, T Yanaihara, T Nakayama. Serum steroid levels in children at birth and in early neonatal period. American journal of obstetrics and gynecology. 1981 Aug; 140(8):961-5. doi: 10.1016/0002-9378(81)90092-2. [PMID: 6455919]
  • T Kozaki, M Hashino, M Maruyama, T Yanaihara, T Nakayama, H Mori. [Changes of dehydroepiandrosterone (DHA), 16 alpha OH-DHA and estriol levels in maternal peripheral blood during late pregnancy and labor--measured by gas chromatography-mass spectrometry with application of deuterated steroids as internal standards (author's transl)]. Acta obstetrica et gynaecologica Japonica. 1981 Jul; 33(7):935-44. doi: NULL. [PMID: 6458197]
  • T Laatikainen, J Pelkonen, D Apter, T Ranta. Fetal and maternal serum levels of steroid sulfates, unconjugated steroids, and prolactin at term pregnancy and in early spontaneous labor. The Journal of clinical endocrinology and metabolism. 1980 Mar; 50(3):489-94. doi: 10.1210/jcem-50-3-489. [PMID: 6444637]
  • T J Laatikainen, J I Peltonen. Amniotic fluid estriol, estriol precursors, and pregnanediol in intrauterine growth retardation. Journal of steroid biochemistry. 1980 Mar; 13(3):265-9. doi: 10.1016/0022-4731(80)90004-7. [PMID: 6446624]
  • G Phillipou, R F Seamark, R Sweet. Prenatal diagnosis of placental sulphatase deficiency. The Australian & New Zealand journal of obstetrics & gynaecology. 1979 Nov; 19(4):233-6. doi: 10.1111/j.1479-828x.1979.tb01381.x. [PMID: 161704]
  • J D Madden, N F Gant, P C MacDonald. Study of the kinetics of conversion of maternal plasma dehydroisoandrosterone sulfate to 16 alpha-hydroxydehydroisoandrosterone sulfate, estradiol, and estriol. American journal of obstetrics and gynecology. 1978 Oct; 132(4):392-5. doi: 10.1016/0002-9378(78)90773-1. [PMID: 152062]
  • J Weidenfeld, J M Shaefer, H Landau, M Schiller, Z Zadik. 11 beta-Hydroxydehydroepiandrosterone in a case of virilizing adrenal adenoma: isolation from urine and mitochondrial conversion from dehydroepiandrosterone. The Journal of clinical endocrinology and metabolism. 1978 Jul; 47(1):102-4. doi: 10.1210/jcem-47-1-102. [PMID: 162514]
  • W Nowaczynski, F H Messeril, O Kuchel, G P Guthrie, J Genest. Origin of urinary 16 beta-hydroxydehydroepiandrosterone in essential hypertension. The Journal of clinical endocrinology and metabolism. 1977 Apr; 44(4):629-38. doi: 10.1210/jcem-44-4-629. [PMID: 139414]
  • H Sekihara, J A Sennett, G W Liddle, T J McKenna, L R Yarbro. Plasma 16 beta-hydroxydehydroepiandrosterone in normal and pathological conditions in man. The Journal of clinical endocrinology and metabolism. 1976 Nov; 43(5):1078-84. doi: 10.1210/jcem-43-5-1078. [PMID: 186475]
  • M C Ruiz Gonzalez, J Martinez Venano, A Oriol-Bosch. The effect of dehydroepiandrosterone sulfate administration on the 16alpha-hydroxy-dehydroepiandrosterone excretion in cirrhotic patients. Journal of steroid biochemistry. 1976 Oct; 7(10):862-6. doi: 10.1016/0022-4731(76)90191-6. [PMID: 138027]
  • K FOTHERBY, A COLAS, S M ATHERDEN, G F MARRIAN. The isolation of 16alpha-hydroxydehydroepiandrosterone (3 beta:16 alpha-dihydroxyandrost-5-en-17-one) from the urine of normal men. The Biochemical journal. 1957 Aug; 66(4):664-9. doi: 10.1042/bj0660664. [PMID: 13459916]