4-oxo-Retinoic acid (BioDeep_00000019605)

 

Secondary id: BioDeep_00000011347, BioDeep_00001874726

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

化学式: C20H26O3 (314.1881846)
中文名称: 4-氧代-维A酸, 4 - 氧代视黄酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.95%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

4-oxo-Retinoic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-oxo-retinoic_acid (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000019605). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C(C)(C)C(/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)=C(C)C(=O)C1
InChI: InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

描述信息

4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545) [HMDB]
4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545).
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs).

同义名列表

22 个代谢物同义名

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; 4-Oxoretinoic acid, (13-cis)-isomer; all-trans 4-Keto Retinoic Acid; 4-oxo-all-trans-Retinoic acid; all-trans-4-Oxoretinoic acid; 4-oxo-13-cis-Retinoic acid; 4-oxo-all-trans-Retinoate; 4-oxo-trans-Retinoic acid; all-trans-4-Oxoretinoate; 4-Keto-retinoic acid; 4-oxo-Retinoic acid; 4-Ketoretinoic acid; 4-Oxoretinoic acid; 4-oxo-Isotretinoin; 4-Keto-retinoate; 4-oxo-Retinoate; 4-Ketoretinoate; 4-Oxotretinoin; 4-Oxoretinoate; Ro 12-4824; Ro 11-4824; 4-oxo-AtRA



数据库引用编号

14 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

  • Poonam Sonawane, Hwang Eui Cho, Ashujit Tagde, Dattesh Verlekar, Alice L Yu, C Patrick Reynolds, Min H Kang. Metabolic characteristics of 13-cis-retinoic acid (isotretinoin) and anti-tumour activity of the 13-cis-retinoic acid metabolite 4-oxo-13-cis-retinoic acid in neuroblastoma. British journal of pharmacology. 2014 Dec; 171(23):5330-44. doi: 10.1111/bph.12846. [PMID: 25039756]
  • F Grønhøj Larsen, P Jakobsen, C Grønhøj Larsen, M Heidenheim, E Held, F Nielsen-Kudsk. The metabolism and pharmacokinetics of isotretinoin in patients with acne and rosacea are not influenced by ethanol. The British journal of dermatology. 2009 Sep; 161(3):664-70. doi: 10.1111/j.1365-2133.2009.09241.x. [PMID: 19563582]
  • Olivier Sorg, Christian Tran, Pierre Carraux, Denise Grand, Christelle Barraclough, Jean-François Arrighi, Patrick Descombes, Vincent Piguet, Jean-Hilaire Saurat. Metabolism and biological activities of topical 4-oxoretinoids in mouse skin. The Journal of investigative dermatology. 2008 Apr; 128(4):999-1008. doi: 10.1038/sj.jid.5701106. [PMID: 17943179]
  • Thomas E Gundersen, Nasser E Bastani, Rune Blomhoff. Quantitative high-throughput determination of endogenous retinoids in human plasma using triple-stage liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2007; 21(7):1176-86. doi: 10.1002/rcm.2946. [PMID: 17330217]
  • Sherry A Ferguson, Paul H Siitonen, F Javier Cisneros, Bobby Gough, John F Young. Steady state pharmacokinetics of oral treatment with 13-cis-retinoic acid or all-trans-retinoic acid in male and female adult rats. Basic & clinical pharmacology & toxicology. 2006 Jun; 98(6):582-7. doi: 10.1111/j.1742-7843.2006.pto_359.x. [PMID: 16700821]
  • Ralph Rühl. Method to determine 4-oxo-retinoic acids, retinoic acids and retinol in serum and cell extracts by liquid chromatography/diode-array detection atmospheric pressure chemical ionisation tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2006; 20(16):2497-504. doi: 10.1002/rcm.2621. [PMID: 16862622]
  • Virginie E Bérubé, Monique H Boily, Chistian DeBlois, Nathalie Dassylva, Philip A Spear. Plasma retinoid profile in bullfrogs, Rana catesbeiana, in relation to agricultural intensity of sub-watersheds in the Yamaska River drainage basin, Québec, Canada. Aquatic toxicology (Amsterdam, Netherlands). 2005 Jan; 71(2):109-20. doi: 10.1016/j.aquatox.2004.10.018. [PMID: 15642636]
  • Ralph Rühl, Florian J Schweigert. Automated solid-phase extraction and liquid chromatographic method for retinoid determination in biological samples. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Dec; 798(2):309-16. doi: 10.1016/j.jchromb.2003.10.001. [PMID: 14643511]
  • M Berggren Söderlund, G Fex, P Nilsson-Ehle. Decreasing serum concentrations of all-trans, 13-cis retinoic acids and retinol during fasting and caloric restriction. Journal of internal medicine. 2003 Mar; 253(3):375-80. doi: 10.1046/j.1365-2796.2003.01114.x. [PMID: 12603506]
  • Carsten K Schmidt, Jutta Volland, Gerd Hamscher, Heinz Nau. Characterization of a new endogenous vitamin A metabolite. Biochimica et biophysica acta. 2002 Jul; 1583(2):237-51. doi: 10.1016/s1388-1981(02)00212-3. [PMID: 12117568]
  • James V Chithalen, Luong Luu, Martin Petkovich, Glenville Jones. HPLC-MS/MS analysis of the products generated from all-trans-retinoic acid using recombinant human CYP26A. Journal of lipid research. 2002 Jul; 43(7):1133-42. doi: 10.1194/jlr.m100343-jlr200. [PMID: 12091498]
  • Xiaojia Guo, Beatrice S Knudsen, Donna M Peehl, Alberto Ruiz, Dean Bok, Robert R Rando, Johng S Rhim, David M Nanus, Lorraine J Gudas. Retinol metabolism and lecithin:retinol acyltransferase levels are reduced in cultured human prostate cancer cells and tissue specimens. Cancer research. 2002 Mar; 62(6):1654-61. doi: . [PMID: 11912136]
  • X Guo, D M Nanus, A Ruiz, R R Rando, D Bok, L J Gudas. Reduced levels of retinyl esters and vitamin A in human renal cancers. Cancer research. 2001 Mar; 61(6):2774-81. doi: NULL. [PMID: 11289161]
  • C Liu, R M Russell, H K Seitz, X D Wang. Ethanol enhances retinoic acid metabolism into polar metabolites in rat liver via induction of cytochrome P4502E1. Gastroenterology. 2001 Jan; 120(1):179-89. doi: 10.1053/gast.2001.20877. [PMID: 11208727]
  • M Ahmad, M Ahmadi, P J Nicholls, H J Smith. In-vitro metabolism of retinoic acid by different tissues from male rats. The Journal of pharmacy and pharmacology. 2000 May; 52(5):511-5. doi: 10.1211/0022357001774291. [PMID: 10864138]
  • I Nulman, M Berkovitch, J Klein, A Pastuszak, R S Lester, N Shear, G Koren. Steady-state pharmacokinetics of isotretinoin and its 4-oxo metabolite: implications for fetal safety. Journal of clinical pharmacology. 1998 Oct; 38(10):926-30. doi: 10.1002/j.1552-4604.1998.tb04388.x. [PMID: 9807973]
  • B Almond-Roesler, U Blume-Peytavi, S Bisson, M Krahn, E Rohloff, C E Orfanos. Monitoring of isotretinoin therapy by measuring the plasma levels of isotretinoin and 4-oxo-isotretinoin. A useful tool for management of severe acne. Dermatology (Basel, Switzerland). 1998; 196(1):176-81. doi: 10.1159/000017856. [PMID: 9557257]
  • R Wyss, F Bucheli. Determination of endogenous levels of 13-cis-retinoic acid (isotretinoin), all-trans-retinoic acid (tretinoin) and their 4-oxo metabolites in human and animal plasma by high-performance liquid chromatography with automated column switching and ultraviolet detection. Journal of chromatography. B, Biomedical sciences and applications. 1997 Oct; 700(1-2):31-47. doi: 10.1016/s0378-4347(97)00303-4. [PMID: 9390712]
  • C Weber, E Dumont. Pharmacokinetics and pharmacodynamics of 9-cis-retinoic acid in healthy men. Journal of clinical pharmacology. 1997 Jul; 37(7):566-74. doi: 10.1002/j.1552-4604.1997.tb04338.x. [PMID: 9243349]
  • T Teerlink, M P Copper, I Klaassen, B J Braakhuis. Simultaneous analysis of retinol, all-trans- and 13-cis-retinoic acid and 13-cis-4-oxoretinoic acid in plasma by liquid chromatography using on-column concentration after single-phase fluid extraction. Journal of chromatography. B, Biomedical sciences and applications. 1997 Jun; 694(1):83-92. doi: 10.1016/s0378-4347(97)00109-6. [PMID: 9234851]
  • T E Gundersen, E Lundanes, R Blomhoff. Quantitative high-performance liquid chromatographic determination of retinoids in human serum using on-line solid-phase extraction and column switching. Determination of 9-cis-retinoic acid, 13-cis-retinoic acid, all-trans-retinoic acid, 4-oxo-all-trans-retinoicacid and 4-oxo-13-cis-retinoic acid. Journal of chromatography. B, Biomedical sciences and applications. 1997 Mar; 691(1):43-58. doi: 10.1016/s0378-4347(96)00434-3. [PMID: 9140757]
  • B J Braakhuis, I Klaassen, B M van der Leede, J Cloos, R H Brakenhoff, M P Copper, T Teerlink, H F Hendriks, P T van der Saag, G B Snow. Retinoid metabolism and all-trans retinoic acid-induced growth inhibition in head and neck squamous cell carcinoma cell lines. British journal of cancer. 1997; 76(2):189-97. doi: 10.1038/bjc.1997.361. [PMID: 9231918]
  • 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]
  • G A Fex, S Andréasson, B Ehinger. Serum retinoids in retinitis pigmentosa patients treated with vitamin A. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie. 1996 Aug; 234 Suppl 1(?):S18-21. doi: 10.1007/bf02343043. [PMID: 8871145]
  • K Takitani, H Tamai, T Morinobu, N Kawamura, M Miyake, T Fujimoto, M Mino. 4-oxo retinoic acid for refractory acute promyelocytic leukemia in children with all-trans retinoic acid therapy. Journal of nutritional science and vitaminology. 1995 Aug; 41(4):493-8. doi: 10.3177/jnsv.41.493. [PMID: 8676222]
  • C Eckhoff, S Chari, M Kromka, H Staudner, L Juhasz, H Rudiger, N Agnish. Teratogenicity and transplacental pharmacokinetics of 13-cis-retinoic acid in rabbits. Toxicology and applied pharmacology. 1994 Mar; 125(1):34-41. doi: 10.1006/taap.1994.1046. [PMID: 8128493]
  • J Van Wauwe, M C Coene, W Cools, J Goossens, W Lauwers, L Le Jeune, C Van Hove, G Van Nyen. Liarozole fumarate inhibits the metabolism of 4-keto-all-trans-retinoic acid. Biochemical pharmacology. 1994 Feb; 47(4):737-41. doi: 10.1016/0006-2952(94)90137-6. [PMID: 8129749]
  • G Tzimas, H Bürgin, M D Collins, H Hummler, H Nau. The high sensitivity of the rabbit to the teratogenic effects of 13-cis-retinoic acid (isotretinoin) is a consequence of prolonged exposure of the embryo to 13-cis-retinoic acid and 13-cis-4-oxo-retinoic acid, and not of isomerization to all-trans-retinoic acid. Archives of toxicology. 1994; 68(2):119-28. doi: 10.1007/s002040050044. [PMID: 8179481]
  • C Eckhoff, M D Collins, H Nau. Human plasma all-trans-, 13-cis- and 13-cis-4-oxoretinoic acid profiles during subchronic vitamin A supplementation: comparison to retinol and retinyl ester plasma levels. The Journal of nutrition. 1991 Jul; 121(7):1016-25. doi: 10.1093/jn/121.7.1016. [PMID: 2051220]
  • B K Jensen, L A McGann, V Kachevsky, T J Franz. The negligible systemic availability of retinoids with multiple and excessive topical application of isotretinoin 0.05\% gel (Isotrex) in patients with acne vulgaris. Journal of the American Academy of Dermatology. 1991 Mar; 24(3):425-8. doi: 10.1016/0190-9622(91)70065-a. [PMID: 1829464]
  • C Eckhoff, H Nau. Identification and quantitation of all-trans- and 13-cis-retinoic acid and 13-cis-4-oxoretinoic acid in human plasma. Journal of lipid research. 1990 Aug; 31(8):1445-54. doi: NULL. [PMID: 2280185]
  • C Eckhoff, H Nau. Vitamin A supplementation increases levels of retinoic acid compounds in human plasma: possible implications for teratogenesis. Archives of toxicology. 1990; 64(6):502-3. doi: 10.1007/bf01977634. [PMID: 2275606]
  • W L Davis, L A Crawford, O J Cooper, G R Farmer, D Thomas, B L Freeman. Generation of radical oxygen species by neural crest cells treated in vitro with isotretinoin and 4-oxo-isotretinoin. Journal of craniofacial genetics and developmental biology. 1990; 10(3):295-310. doi: NULL. [PMID: 2175753]
  • J Creech Kraft, B Löfberg, I Chahoud, G Bochert, H Nau. Teratogenicity and placental transfer of all-trans-, 13-cis-, 4-oxo-all-trans-, and 4-oxo-13-cis-retinoic acid after administration of a low oral dose during organogenesis in mice. Toxicology and applied pharmacology. 1989 Aug; 100(1):162-76. doi: 10.1016/0041-008x(89)90099-9. [PMID: 2763297]
  • M A Satre, J D Penner, D M Kochhar. Pharmacokinetic assessment of teratologically effective concentrations of an endogenous retinoic acid metabolite. Teratology. 1989 Apr; 39(4):341-8. doi: 10.1002/tera.1420390406. [PMID: 2749577]
  • W B Howard, C C Willhite, S T Omaye, R P Sharma. Comparative distribution, pharmacokinetics and placental permeabilities of all-trans-retinoic acid, 13-cis-retinoic acid, all-trans-4-oxo-retinoic acid, retinyl acetate and 9-cis-retinal in hamsters. Archives of toxicology. 1989; 63(2):112-20. doi: 10.1007/bf00316432. [PMID: 2730336]
  • R Wyss, F Bucheli. Quantitative analysis of retinoids in biological fluids by high-performance liquid chromatography using column switching. I. Determination of isotretinoin and tretinoin and their 4-oxo metabolites in plasma. Journal of chromatography. 1988 Feb; 424(2):303-14. doi: 10.1016/s0378-4347(00)81107-x. [PMID: 3131376]
  • Y M Peng, M J Xu, D S Alberts. Analysis and stability of retinol in plasma. Journal of the National Cancer Institute. 1987 Jan; 78(1):95-9. doi: 10.1093/jnci/78.1.95. [PMID: 3467133]
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  • A B Barua, J A Olson. Metabolism and biological activity of all-trans 4,4-difluororetinyl acetate. Biochimica et biophysica acta. 1984 Jun; 799(2):128-34. doi: 10.1016/0304-4165(84)90286-1. [PMID: 6547353]
  • R K Brazzell, W A Colburn. Pharmacokinetics of the retinoids isotretinoin and etretinate. A comparative review. Journal of the American Academy of Dermatology. 1982 Apr; 6(4 Pt 2 Suppl):643-51. doi: 10.1016/s0190-9622(82)70053-2. [PMID: 6461675]