4-Oxoisotretinoin (BioDeep_00000616421)
代谢物信息卡片
4-Keto 13-cis-Retinoic Acid
化学式: C20H26O3 (314.1881846)
中文名称: 4-酮13-顺式视黄酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
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
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
同义名列表
2 个代谢物同义名
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)
0 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] - 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:
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Cancer research.
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Cancer research.
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Gastroenterology.
2001 Jan; 120(1):179-89. doi:
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The Journal of pharmacy and pharmacology.
2000 May; 52(5):511-5. doi:
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Journal of clinical pharmacology.
1998 Oct; 38(10):926-30. doi:
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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:
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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.
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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:
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The Journal of nutrition.
1991 Jul; 121(7):1016-25. doi:
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Journal of the American Academy of Dermatology.
1991 Mar; 24(3):425-8. doi:
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Journal of lipid research.
1990 Aug; 31(8):1445-54. doi:
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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:
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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.
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1988 Feb; 424(2):303-14. doi:
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