Retinoyl b-glucuronide (BioDeep_00000004296)

 

Secondary id: BioDeep_00001875368

human metabolite Endogenous blood metabolite


代谢物信息卡片


1-O-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-β-D-glucopyranuronic acid O(15)-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]retinoic acid

化学式: C26H36O8 (476.241)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 31.72%

分子结构信息

SMILES: C/C(=C\C=C\C(=C\C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)\C)/C=C/C1=C(C)CCCC1(C)C
InChI: InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1

描述信息

Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers. [HMDB]
Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

32 个代谢物同义名

1-O-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-β-D-glucopyranuronic acid O(15)-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]retinoic acid; 1-O-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-beta-D-glucopyranuronic acid O(15)-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]retinoic acid; (2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid; 13-cis-Retinoic acid acyl beta-delta-glucuronide; 1-O-all-trans-retinoyl-β-glucuronic acid; 13-cis-Retinoic acid acyl beta-D-glucuronide; 1-O-all-trans-retinoyl-beta-glucuronic acid; all-trans-Retinoyl-beta-delta-glucuronide; 13-cis-Retinoyl-beta-delta-glucuronide; all-trans-Retinoyl-beta-D-glucuronide; 9-cis-Retinoyl-beta-delta-glucuronide; all-trans-Retinoyl-β-glucuronide; Retinoic acid beta-delta-glucuronide; all-trans-Retinoyl-beta-glucuronide; 13-cis-Retinoyl-beta-D-glucuronide; 9-cis-Retinoyl-beta-D-glucuronide; all-trans-Retinoyl-b-glucuronide; 13-cis-Retinoyl-beta-glucuronide; Retinoic acid beta-D-glucuronide; all-trans-Retinoyl-β-glucuronide; 13-cis-Retinoyl glucuronide; trans-Retinoyl glucuronide; Retinoyl-beta-glucuronide; Retinoyl beta-glucuronide; Retinoyl b-glucuronide; 13-cis-Retinoic acid; Retinoyl glucuronide; 13-cis-Retinoate; Retinoic Acid; Glucuronide; Retinoate; all-trans-Retinoyl-beta-glucuronide



数据库引用编号

18 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

9 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(9)

PharmGKB(0)

2 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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 ABCB1, ALB, CYP2C8, HPGDS
Peripheral membrane protein 1 GBA1
Endoplasmic reticulum membrane 9 CYP2C8, UGT1A1, UGT1A3, UGT1A4, UGT1A6, UGT1A8, UGT1A9, UGT2B17, UGT2B7
Nucleus 1 ALB
cytosol 2 ALB, HPGDS
trans-Golgi network 1 GBA1
centrosome 1 ALB
nucleoplasm 1 HPGDS
Cell membrane 3 ABCB1, SLCO1A2, SLCO1B3
Multi-pass membrane protein 7 ABCB1, ABCC3, SLC22A6, SLC22A8, SLC45A2, SLCO1A2, SLCO1B3
cell surface 1 ABCB1
Golgi apparatus 2 ALB, GBA1
lysosomal membrane 1 GBA1
Lysosome 1 GBA1
plasma membrane 8 ABCB1, ABCC3, CYP2C8, SLC22A6, SLC22A8, SLCO1A2, SLCO1B3, UGT1A1
Membrane 14 ABCB1, ABCC3, SLC22A6, SLC45A2, SLCO1A2, SLCO1B3, UGT1A1, UGT1A3, UGT1A4, UGT1A6, UGT1A8, UGT1A9, UGT2B17, UGT2B7
apical plasma membrane 3 ABCB1, SLC22A8, SLCO1A2
basolateral plasma membrane 5 ABCC3, SLC22A6, SLC22A8, SLCO1A2, SLCO1B3
caveola 1 SLC22A6
extracellular exosome 6 ABCB1, ALB, GBA1, SHBG, SLC22A6, SLC22A8
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 8 ALB, GBA1, UGT1A1, UGT1A3, UGT1A4, UGT1A6, UGT1A8, UGT1A9
extracellular space 1 ALB
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 1 UGT1A1
protein-containing complex 2 ALB, SLC22A6
intracellular membrane-bounded organelle 3 CYP2C8, HPGDS, UGT1A6
Secreted 2 ALB, SHBG
extracellular region 2 ALB, SHBG
Single-pass membrane protein 8 UGT1A1, UGT1A3, UGT1A4, UGT1A6, UGT1A8, UGT1A9, UGT2B17, UGT2B7
anchoring junction 1 ALB
Melanosome membrane 1 SLC45A2
Apical cell membrane 1 ABCB1
Cytoplasm, perinuclear region 1 UGT1A1
lateral plasma membrane 1 SLC22A8
ciliary basal body 1 ALB
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Basolateral cell membrane 4 ABCC3, SLC22A6, SLC22A8, SLCO1B3
basal plasma membrane 4 ABCC3, SLC22A6, SLCO1A2, SLCO1B3
endoplasmic reticulum lumen 1 ALB
platelet alpha granule lumen 1 ALB
Basal cell membrane 4 ABCC3, SLC22A6, SLCO1A2, SLCO1B3
external side of apical plasma membrane 1 ABCB1
endoplasmic reticulum chaperone complex 1 UGT1A1
cytochrome complex 1 UGT1A1
ciliary transition fiber 1 ALB


文献列表

  • Sherry A Tanumihardjo. Vitamin A: biomarkers of nutrition for development. The American journal of clinical nutrition. 2011 Aug; 94(2):658S-65S. doi: 10.3945/ajcn.110.005777. [PMID: 21715511]
  • Grover P Miller, Drew R Jones, Shane Z Sullivan, Anna Mazur, Suzanne N Owen, Neil C Mitchell, Anna Radominska-Pandya, Jeffery H Moran. Assessing cytochrome P450 and UDP-glucuronosyltransferase contributions to warfarin metabolism in humans. Chemical research in toxicology. 2009 Jul; 22(7):1239-45. doi: 10.1021/tx900031z. [PMID: 19408964]
  • Pulin C Sarma, Bhabesh C Goswami, Krishna Gogoi, Harsha Bhattacharjee, Arun B Barua. A new approach to the assessment of marginal vitamin A deficiency in children in suburban Guwahati, India: hydrolysis of retinoyl glucuronide to retinoic acid. The British journal of nutrition. 2009 Mar; 101(6):794-7. doi: 10.1017/s0007114508047739. [PMID: 19283884]
  • Hugo Girard, Jean Thibaudeau, Michael H Court, Louis-Charles Fortier, Lyne Villeneuve, Patrick Caron, Qin Hao, Lisa L von Moltke, David J Greenblatt, Chantal Guillemette. UGT1A1 polymorphisms are important determinants of dietary carcinogen detoxification in the liver. Hepatology (Baltimore, Md.). 2005 Aug; 42(2):448-57. doi: 10.1002/hep.20770. [PMID: 15986396]
  • Aloys L A Sesink, Ilja C W Arts, Vincent C J de Boer, Pauline Breedveld, Jan H M Schellens, Peter C H Hollman, Frans G M Russel. Breast cancer resistance protein (Bcrp1/Abcg2) limits net intestinal uptake of quercetin in rats by facilitating apical efflux of glucuronides. Molecular pharmacology. 2005 Jun; 67(6):1999-2006. doi: 10.1124/mol.104.009753. [PMID: 15749994]
  • Bhabesh C Goswami, Abigail K Reida, Kristi D Ivanoff, Arun B Barua, James A Olson. Intestinal absorption and metabolism of retinoyl beta-glucuronide in humans, and of 15-[14C]-retinoyl beta-glucuronide in rats of different vitamin A status. The Journal of nutritional biochemistry. 2003 Dec; 14(12):703-9. doi: 10.1016/j.jnutbio.2003.08.008. [PMID: 14690762]
  • N Sidell, M Pasquali, S Malkapuram, A B Barua, T Wanichkul, R K Wada. In vitro and in vivo effects of easily administered, low-toxic retinoid and phenylacetate compounds on human neuroblastoma cells. British journal of cancer. 2003 Jul; 89(2):412-9. doi: 10.1038/sj.bjc.6601108. [PMID: 12865937]
  • David A Romans, Arun B Barua, James Allen Olson. Pharmacokinetics of all-trans retinoyl beta-glucuronide in rats following intraperitoneal and oral administration. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2003 Jul; 73(4):251-7. doi: 10.1024/0300-9831.73.4.251. [PMID: 12951897]
  • Jack M Gallup, Branka Grubor, Arun B Barua, Gholamreza Mohammadi, Kim A Brogden, James A Olson, Mark R Ackermann. Repeated intravenous doses of all-trans-retinoyl beta-D-glucuronide is not effective in the treatment of bacterial bronchopneumonia in lambs but is devoid of gross and acute toxicity. Medical science monitor : international medical journal of experimental and clinical research. 2002 Sep; 8(9):BR345-53. doi: NULL. [PMID: 12218935]
  • H S Lin, A B Barua, J A Olson, K S Low, S Y Chan, M L Shoon, P C Ho. Pharmacokinetic study of all-trans-retinoyl-beta-D-glucuronide in Sprague-Dawley rats after single and multiple intravenous administration(s). Journal of pharmaceutical sciences. 2001 Dec; 90(12):2023-31. doi: 10.1002/jps.1153. [PMID: 11745761]
  • R Rühl, J O Sass, H Nau, S Klug. Effects of all-trans-retinoic acid and all-trans-retinoyl glucuronide in two in vitro systems of distinct biological complexity. Archives of toxicology. 2001 Oct; 75(8):497-504. doi: 10.1007/s002040100257. [PMID: 11757674]
  • N Sidell, S Sawatsri, M J Connor, A B Barua, J A Olson, R K Wada. Pharmacokinetics of chronically administered all-trans-retinoyl-beta-glucuronide in mice. Biochimica et biophysica acta. 2000 Oct; 1502(2):264-72. doi: 10.1016/s0925-4439(00)00052-1. [PMID: 11040451]
  • S Kaul, J A Olson. Effect of vitamin A deficiency on the hydrolysis of retinoyl beta-glucuronide to retinoic acid by rat tissue organelles in vitro. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1998; 68(4):232-6. doi: . [PMID: 9706497]
  • A B Barua, P K Duitsman, D Kostic, M Barua, J A Olson. Reduction of serum retinol levels following a single oral dose of all-trans retinoic acid in humans. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1997; 67(6):423-6. doi: NULL. [PMID: 9433675]
  • H Nau, M M Elmazar, R Rühl, R Thiel, J O Sass. All-trans-retinoyl-beta-glucuronide is a potent teratogen in the mouse because of extensive metabolism to all-trans-retinoic acid. Teratology. 1996 Sep; 54(3):150-6. doi: 10.1002/(sici)1096-9926(199609)54:3<150::aid-tera5>3.0.co;2-7. [PMID: 8987158]
  • B Becker, A B Barua, J A Olson. All-trans-retinoyl beta-glucuronide: new procedure for chemical synthesis and its metabolism in vitamin A-deficient rats. The Biochemical journal. 1996 Feb; 314 ( Pt 1)(?):249-52. doi: 10.1042/bj3140249. [PMID: 8660290]
  • A B Barua, J A Olson. Percutaneous absorption, excretion and metabolism of all-trans-retinoyl beta-glucuronide and of all-trans-retinoic acid in the rat. Skin pharmacology : the official journal of the Skin Pharmacology Society. 1996; 9(1):17-26. doi: 10.1159/000211386. [PMID: 8868029]
  • J O Sass, E Masgrau, J H Saurat, H Nau. Metabolism of oral 9-cis-retinoic acid in the human. Identification of 9-cis-retinoyl-beta-glucuronide and 9-cis-4-oxo-retinoyl-beta-glucuronide as urinary metabolites. Drug metabolism and disposition: the biological fate of chemicals. 1995 Sep; 23(9):887-91. doi: NULL. [PMID: 8565776]
  • J O Sass, G Tzimas, H Nau. 9-cis-retinoyl-beta-D-glucuronide is a major metabolite of 9-cis-retinoic acid. Life sciences. 1994; 54(6):PL69-74. doi: 10.1016/0024-3205(94)00703-9. [PMID: 8295481]
  • K L Salyers, M E Cullum, M H Zile. Glucuronidation of all-trans-retinoic acid in liposomal membranes. Biochimica et biophysica acta. 1993 Nov; 1152(2):328-34. doi: 10.1016/0005-2736(93)90265-2. [PMID: 8218334]
  • D B Gunning, A B Barua, J A Olson. Comparative teratogenicity and metabolism of all-trans retinoic acid, all-trans retinoyl beta-glucose, and all-trans retinoyl beta-glucuronide in pregnant Sprague-Dawley rats. Teratology. 1993 Jan; 47(1):29-36. doi: 10.1002/tera.1420470107. [PMID: 8475455]
  • A B Barua, D B Gunning, J A Olson. Metabolism in vivo of all-trans-[11-3H]retinoic acid after an oral dose in rats. Characterization of retinoyl beta-glucuronide in the blood and other tissues. The Biochemical journal. 1991 Jul; 277 ( Pt 2)(?):527-31. doi: 10.1042/bj2770527. [PMID: 1859380]
  • J C Kraft, W Slikker, J R Bailey, L G Roberts, B Fischer, W Wittfoht, H Nau. Plasma pharmacokinetics and metabolism of 13-cis- and all-trans-retinoic acid in the cynomolgus monkey and the identification of 13-cis- and all-trans-retinoyl-beta-glucuronides. A comparison to one human case study with isotretinoin. Drug metabolism and disposition: the biological fate of chemicals. 1991 Mar; 19(2):317-24. doi: NULL. [PMID: 1676630]
  • J Creech Kraft, C Eckhoff, D M Kochhar, G Bochert, I Chahoud, H Nau. Isotretinoin (13-cis-retinoic acid) metabolism, cis-trans isomerization, glucuronidation, and transfer to the mouse embryo: consequences for teratogenicity. Teratogenesis, carcinogenesis, and mutagenesis. 1991; 11(1):21-30. doi: 10.1002/tcm.1770110104. [PMID: 1677495]
  • D C Harnish, A B Barua, K J Soprano, D R Soprano. Induction of beta-retinoic acid receptor mRNA by teratogenic doses of retinoids in murine fetuses. Differentiation; research in biological diversity. 1990 Nov; 45(2):103-8. doi: 10.1111/j.1432-0436.1990.tb00463.x. [PMID: 1965892]
  • A B Barua, J A Olson. Chemical synthesis of all-trans-[11-3H]retinoyl beta-glucuronide and its metabolism in rats in vivo. The Biochemical journal. 1989 Oct; 263(2):403-9. doi: 10.1042/bj2630403. [PMID: 2597112]
  • P A Bank, K L Salyers, M H Zile. Effect of tetrachlorodibenzo-p-dioxin (TCDD) on the glucuronidation of retinoic acid in the rat. Biochimica et biophysica acta. 1989 Oct; 993(1):1-6. doi: 10.1016/0304-4165(89)90134-7. [PMID: 2508757]
  • A B Barua, R O Batres, J A Olson. Characterization of retinyl beta-glucuronide in human blood. The American journal of clinical nutrition. 1989 Aug; 50(2):370-4. doi: 10.1093/ajcn/50.2.370. [PMID: 2756924]
  • A B Barua, R O Batres, J A Olson. Synthesis and metabolism of all-trans-[11-3H]retinyl beta-glucuronide in rats in vivo. The Biochemical journal. 1988 Jun; 252(2):415-20. doi: 10.1042/bj2520415. [PMID: 3415665]
  • A B Barua, J A Olson. Retinoyl beta-glucuronide: an endogenous compound of human blood. The American journal of clinical nutrition. 1986 Apr; 43(4):481-5. doi: 10.1093/ajcn/43.4.481. [PMID: 3962900]
  • D A Miller, H F DeLuca. Biosynthesis of retinoyl-beta-glucuronide, a biologically active metabolite of all-trans-retinoic acid. Archives of biochemistry and biophysics. 1986 Jan; 244(1):179-86. doi: 10.1016/0003-9861(86)90107-4. [PMID: 3080946]
  • A B Barua, J A Olson. Chemical synthesis of all-trans retinoyl beta-glucuronide. Journal of lipid research. 1985 Oct; 26(10):1277-82. doi: . [PMID: 3906006]
  • H F DeLuca, M Zile, W K Sietsema. The metabolism of retinoic acid to 5,6-epoxyretinoic acid, retinoyl-beta-glucuronide, and other polar metabolites. Annals of the New York Academy of Sciences. 1981 Feb; 359(?):25-36. doi: 10.1111/j.1749-6632.1981.tb12734.x. [PMID: 6942675]