3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid (BioDeep_00000172589)
human metabolite blood metabolite
代谢物信息卡片
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
化学式: C20H28O2 (300.2089)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 15.27%
分子结构信息
SMILES: CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O
InChI: InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)
描述信息
同义名列表
20 个代谢物同义名
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; (all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate; 3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate; all-trans-Vitamin a1 acid; all-trans-Vitamin a acid; all-(e)-Retinoic acid; all-trans-Tretinoin; all-trans-Retinoate; trans-Retinoic acid; beta-Retinoic acid; all-(e)-Retinoate; trans-Retinoate; Vitamin a acid; beta-Retinoate; Retinoic Acid; Isotretinoin; Retinoate; Tretin m
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:26536
- PubChem: 5538
- HMDB: HMDB0244343
- ChEMBL: CHEMBL1235644
- Wikipedia: Tretinoin
- chemspider: 5337
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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
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Nutrition research and practice.
2012 Apr; 6(2):113-9. doi:
10.4162/nrp.2012.6.2.113. [PMID: 22586499] - Savithri Balasubramanian, Marcel Jansen, M Todd Valerius, Benjamin D Humphreys, Terry B Strom. Orphan nuclear receptor Nur77 promotes acute kidney injury and renal epithelial apoptosis.
Journal of the American Society of Nephrology : JASN.
2012 Apr; 23(4):674-86. doi:
10.1681/asn.2011070646. [PMID: 22343121] - Christoph Grüber, Ceylan Taner, Johanna Mihály, Paolo M Matricardi, Ulrich Wahn, Ralph Rühl. Serum retinoic acid and atopy among children of different ethnic origin living in Germany.
Journal of pediatric gastroenterology and nutrition.
2012 Apr; 54(4):558-60. doi:
10.1097/mpg.0b013e318240bc87. [PMID: 22167012] - G Dell'Acqua, K Schweikert. Skin benefits of a myconoside-rich extract from resurrection plant Haberlea rhodopensis.
International journal of cosmetic science.
2012 Apr; 34(2):132-9. doi:
10.1111/j.1468-2494.2011.00692.x. [PMID: 22023081] - Yukary Nakamura, Noritaka Nakamichi, Takeshi Takarada, Kiyokazu Ogita, Yukio Yoneda. Transferrin receptor-1 suppresses neurite outgrowth in neuroblastoma Neuro2A cells.
Neurochemistry international.
2012 Apr; 60(5):448-57. doi:
10.1016/j.neuint.2011.08.018. [PMID: 22019713] - Shi Zhao, Rui Li, Yang Li, Wei Chen, Yan Zhang, Guoxun Chen. Roles of vitamin A status and retinoids in glucose and fatty acid metabolism.
Biochemistry and cell biology = Biochimie et biologie cellulaire.
2012 Apr; 90(2):142-52. doi:
10.1139/o11-079. [PMID: 22292422] - Maurice H J Selman, Sanne E de Jong, Darius Soonawala, Frank P Kroon, Ayola Akim Adegnika, André M Deelder, Cornelis H Hokke, Maria Yazdanbakhsh, Manfred Wuhrer. Changes in antigen-specific IgG1 Fc N-glycosylation upon influenza and tetanus vaccination.
Molecular & cellular proteomics : MCP.
2012 Apr; 11(4):M111.014563. doi:
10.1074/mcp.m111.014563. [PMID: 22184099] - Hanne Fredly, Håkon Reikvam, Bjørn Tore Gjertsen, Oystein Bruserud. Disease-stabilizing treatment with all-trans retinoic acid and valproic acid in acute myeloid leukemia: serum hsp70 and hsp90 levels and serum cytokine profiles are determined by the disease, patient age, and anti-leukemic treatment.
American journal of hematology.
2012 Apr; 87(4):368-76. doi:
10.1002/ajh.23116. [PMID: 22374841] - Yue Hu, Junwei Sun, Jing Wang, Long Wang, Yaofu Bai, Meng Yu, Zhimin Lian, Shanshan Zhang, Jinlian Hua. Characterization of female germ-like cells derived from mouse embryonic stem cells through expression of GFP under the control of Figla promoter.
Journal of cellular biochemistry.
2012 Apr; 113(4):1111-21. doi:
10.1002/jcb.24044. [PMID: 22213070] - D Ramya, Siddikuzzaman, A Manjamalai, V M Berlin Grace. Chemoprotective effect of all-trans retinoic acid (ATRA) on oxidative stress and lung metastasis induced by benzo(a)pyrene.
Immunopharmacology and immunotoxicology.
2012 Apr; 34(2):317-25. doi:
10.3109/08923973.2011.604087. [PMID: 22066884] - Ana B Fernández-Martínez, María I Arenas Jiménez, Francisco J Lucio Cazaña. Retinoic acid increases hypoxia-inducible factor-1α through intracrine prostaglandin E(2) signaling in human renal proximal tubular cells HK-2.
Biochimica et biophysica acta.
2012 Apr; 1821(4):672-83. doi:
10.1016/j.bbalip.2012.01.010. [PMID: 22306363] - Kenjiro Ono, Masahito Yamada. Vitamin A and Alzheimer's disease.
Geriatrics & gerontology international.
2012 Apr; 12(2):180-8. doi:
10.1111/j.1447-0594.2011.00786.x. [PMID: 22221326] - Hung Chang, Ming-Chung Kuo, Lee-Yung Shih, Po Dunn, Po-Nan Wang, Jin-Hou Wu, Tung-Liang Lin, Yu-Shin Hung, Tzung-Chih Tang. Clinical bleeding events and laboratory coagulation profiles in acute promyelocytic leukemia.
European journal of haematology.
2012 Apr; 88(4):321-8. doi:
10.1111/j.1600-0609.2011.01747.x. [PMID: 22221178] - Chao-Hung Chen, Tusty-Jiuan Hsieh, Kun-Der Lin, Hsing-Yi Lin, Mei-Yueh Lee, Wei-Wen Hung, Pi-Jung Hsiao, Shyi-Jang Shin. Increased unbound retinol-binding protein 4 concentration induces apoptosis through receptor-mediated signaling.
The Journal of biological chemistry.
2012 Mar; 287(13):9694-9707. doi:
10.1074/jbc.m111.301721. [PMID: 22308028] - Liraz Levi, Tamar Ziv, Arie Admon, Berta Levavi-Sivan, Esther Lubzens. Insight into molecular pathways of retinal metabolism, associated with vitellogenesis in zebrafish.
American journal of physiology. Endocrinology and metabolism.
2012 Mar; 302(6):E626-44. doi:
10.1152/ajpendo.00310.2011. [PMID: 22205629] - Rudolf Zechner, Robert Zimmermann, Thomas O Eichmann, Sepp D Kohlwein, Guenter Haemmerle, Achim Lass, Frank Madeo. FAT SIGNALS--lipases and lipolysis in lipid metabolism and signaling.
Cell metabolism.
2012 Mar; 15(3):279-91. doi:
10.1016/j.cmet.2011.12.018. [PMID: 22405066] - Keely G McDonald, Matthew R Leach, Kaitlin W M Brooke, Caihong Wang, Leroy W Wheeler, Elyse K Hanly, Christopher W Rowley, Marc S Levin, Michael Wagner, Ellen Li, Rodney D Newberry. Epithelial expression of the cytosolic retinoid chaperone cellular retinol binding protein II is essential for in vivo imprinting of local gut dendritic cells by lumenal retinoids.
The American journal of pathology.
2012 Mar; 180(3):984-997. doi:
10.1016/j.ajpath.2011.11.009. [PMID: 22222225] - Hadas Sherman, Roee Gutman, Nava Chapnik, Jenny Meylan, Johannes le Coutre, Oren Froy. All-trans retinoic acid modifies the expression of clock and disease marker genes.
The Journal of nutritional biochemistry.
2012 Mar; 23(3):209-17. doi:
10.1016/j.jnutbio.2010.11.017. [PMID: 21497500] - Shan Jiang, Chao-xu Wang, Lan Lan, Dan Zhao. Vitamin A deficiency aggravates iron deficiency by upregulating the expression of iron regulatory protein-2.
Nutrition (Burbank, Los Angeles County, Calif.).
2012 Mar; 28(3):281-7. doi:
10.1016/j.nut.2011.08.015. [PMID: 22154532] - Woo-Joo Choi, Earl S Ford, Gary Curhan, James I Rankin, Hyon K Choi. Independent association of serum retinol and β-carotene levels with hyperuricemia: A national population study.
Arthritis care & research.
2012 Mar; 64(3):389-96. doi:
10.1002/acr.20692. [PMID: 22076806] - Akhayacatra Chinsriwongkul, Ponwanit Chareanputtakhun, Tanasait Ngawhirunpat, Theerasak Rojanarata, Warisada Sila-on, Uracha Ruktanonchai, Praneet Opanasopit. Nanostructured lipid carriers (NLC) for parenteral delivery of an anticancer drug.
AAPS PharmSciTech.
2012 Mar; 13(1):150-8. doi:
10.1208/s12249-011-9733-8. [PMID: 22167418] - Christine B Sethna, Kiranmye Reddy, Carolyn Fein-Levy, Howard Trachtman. Nephrotic-range proteinuria in a child with retinoic acid syndrome.
Pediatric nephrology (Berlin, Germany).
2012 Mar; 27(3):485-8. doi:
10.1007/s00467-011-2048-x. [PMID: 22081164] - Suticha Kittayaruksakul, Sunhapas Soodvilai, Nithi Asavapanumas, Chatchai Muanprasat, Varanuj Chatsudthipong. Liver X receptor activation downregulates organic anion transporter 1 (OAT1) in the renal proximal tubule.
American journal of physiology. Renal physiology.
2012 Mar; 302(5):F552-60. doi:
10.1152/ajprenal.00341.2011. [PMID: 22169006] - Samuel L M Arnold, John K Amory, Thomas J Walsh, Nina Isoherranen. A sensitive and specific method for measurement of multiple retinoids in human serum with UHPLC-MS/MS.
Journal of lipid research.
2012 Mar; 53(3):587-598. doi:
10.1194/jlr.d019745. [PMID: 22192917] - Michelle A Elliott, Louis Letendre, Ayalew Tefferi, William J Hogan, Christopher Hook, Scott H Kaufmann, Rajiv K Pruthi, Animesh Pardanani, Kebede H Begna, Aneel A Ashrani, Alexandra P Wolanskyj, Aref Al-Kali, Mark R Litzow. Therapy-related acute promyelocytic leukemia: observations relating to APL pathogenesis and therapy.
European journal of haematology.
2012 Mar; 88(3):237-43. doi:
10.1111/j.1600-0609.2011.01727.x. [PMID: 22023492] - Jeffrey B Eells, Josiah Wilcots, Scott Sisk, Shirley X Guo-Ross. NR4A gene expression is dynamically regulated in the ventral tegmental area dopamine neurons and is related to expression of dopamine neurotransmission genes.
Journal of molecular neuroscience : MN.
2012 Mar; 46(3):545-53. doi:
10.1007/s12031-011-9642-z. [PMID: 21932041] - Michiyasu Ishizawa, Hiroyuki Kagechika, Makoto Makishima. NR4A nuclear receptors mediate carnitine palmitoyltransferase 1A gene expression by the rexinoid HX600.
Biochemical and biophysical research communications.
2012 Feb; 418(4):780-5. doi:
10.1016/j.bbrc.2012.01.102. [PMID: 22310716] - Xueyan Fu, Judith Moreines, Sarah L Booth. Vitamin K supplementation does not prevent bone loss in ovariectomized Norway rats.
Nutrition & metabolism.
2012 Feb; 9(1):12. doi:
10.1186/1743-7075-9-12. [PMID: 22348311] - Qiong-Lin Liang, Xiao-Ping Liang, Yi-Ming Wang, Yuan-Yuan Xie, Rong-Li Zhang, Xi Chen, Rong Gao, Yi-Jun Cheng, Jun Wu, Qing-Bo Xu, Qing-Zhong Xiao, Xue Li, Shu-Feng Lv, Xue-Mei Fan, Hong-Yang Zhang, Qing-Li Zhang, Guo-An Luo. Effective components screening and anti-myocardial infarction mechanism study of the Chinese medicine NSLF6 based on 'system to system' mode.
Journal of translational medicine.
2012 Feb; 10(?):26. doi:
10.1186/1479-5876-10-26. [PMID: 22316391] - Sandi Kwee, Min-Ae Song, Iona Cheng, Lenora Loo, Maarit Tiirikainen. Measurement of circulating cell-free DNA in relation to 18F-fluorocholine PET/CT imaging in chemotherapy-treated advanced prostate cancer.
Clinical and translational science.
2012 Feb; 5(1):65-70. doi:
10.1111/j.1752-8062.2011.00375.x. [PMID: 22376260] - Iván P Uray, Jennifer M Rodenberg, Reid P Bissonnette, Powel H Brown, Michael A Mancini. Cancer-preventive rexinoid modulates neutral lipid contents of mammary epithelial cells through a peroxisome proliferator-activated receptor γ-dependent mechanism.
Molecular pharmacology.
2012 Feb; 81(2):228-38. doi:
10.1124/mol.111.072967. [PMID: 22053058] - Maude Loignon, Hélène Brodeur, Sonia Deschênes, Denis Phaneuf, Pangala V Bhat, Emil Toma. Combination antiretroviral therapy and chronic HIV infection affect serum retinoid concentrations: longitudinal and cross-sectional assessments.
AIDS research and therapy.
2012 Feb; 9(?):3. doi:
10.1186/1742-6405-9-3. [PMID: 22296672] - A Belatik, S Hotchandani, J Bariyanga, H A Tajmir-Riahi. Binding sites of retinol and retinoic acid with serum albumins.
European journal of medicinal chemistry.
2012 Feb; 48(?):114-23. doi:
10.1016/j.ejmech.2011.12.002. [PMID: 22197381] - Justyna Szumiło, Justyna Podlodowska, Wiktor Podlodowski, Elzbieta Starosławska, Franciszek Burdan. [Chemoprevention of oral cancer--clinical and experimental studies].
Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego.
2012 Feb; 32(188):138-42. doi:
". [PMID: 22590920] - Kazuko Sawada, Daisuke Inoue, Yuichiro Wada, Kazunari Sei, Tsuyoshi Nakanishi, Michihiko Ike. Detection of retinoic acid receptor agonistic activity and identification of causative compounds in municipal wastewater treatment plants in Japan.
Environmental toxicology and chemistry.
2012 Feb; 31(2):307-15. doi:
10.1002/etc.741. [PMID: 22095885] - Chao Yuan, Yu-Sheng Zhang, Yan-Na Cheng, Xia Xue, Wen-Fang Xu, Xian-Jun Qu. A112, a tamibarotene dimethylaminoethyl ester, may inhibit human leukemia cell growth more potently than tamibarotene.
Leukemia & lymphoma.
2012 Feb; 53(2):295-304. doi:
10.3109/10428194.2011.614707. [PMID: 21846186] - Yoav Sharoni, Karin Linnewiel-Hermoni, Marina Khanin, Hagar Salman, Anna Veprik, Michael Danilenko, Joseph Levy. Carotenoids and apocarotenoids in cellular signaling related to cancer: a review.
Molecular nutrition & food research.
2012 Feb; 56(2):259-69. doi:
10.1002/mnfr.201100311. [PMID: 22102431] - Noriaki Yamamoto, Takahiro Nakayama, Masahiro Kajita, Tomohiro Miyake, Takashi Iwamoto, Seung Jin Kim, Ayako Sakai, Hideki Ishihara, Yasuhiro Tamaki, Shinzaburo Noguchi. Detection of aberrant promoter methylation of GSTP1, RASSF1A, and RARβ2 in serum DNA of patients with breast cancer by a newly established one-step methylation-specific PCR assay.
Breast cancer research and treatment.
2012 Feb; 132(1):165-73. doi:
10.1007/s10549-011-1575-2. [PMID: 21594664] - Noriyoshi Iriyama, Yuta Yoshino, Bo Yuan, Akira Horikoshi, Yukio Hirabayashi, Yoshihiro Hatta, Hiroo Toyoda, Jin Takeuchi. Speciation of arsenic trioxide metabolites in peripheral blood and bone marrow from an acute promyelocytic leukemia patient.
Journal of hematology & oncology.
2012 Jan; 5(?):1. doi:
10.1186/1756-8722-5-1. [PMID: 22272800] - Masaki Nishikawa, Naomi Yanagawa, Nobuhiko Kojima, Shunsuke Yuri, Peter V Hauser, Oak D Jo, Norimoto Yanagawa. Stepwise renal lineage differentiation of mouse embryonic stem cells tracing in vivo development.
Biochemical and biophysical research communications.
2012 Jan; 417(2):897-902. doi:
10.1016/j.bbrc.2011.12.071. [PMID: 22209845] - Helena Líbalová, Kateřina Uhlířová, Jiří Kléma, Miroslav Machala, Radim J Šrám, Miroslav Ciganek, Jan Topinka. Global gene expression changes in human embryonic lung fibroblasts induced by organic extracts from respirable air particles.
Particle and fibre toxicology.
2012 Jan; 9(?):1. doi:
10.1186/1743-8977-9-1. [PMID: 22239852]
