Eumelanins (BioDeep_00000178947)
human metabolite blood metabolite
代谢物信息卡片
7-(2-amino-2-carboxyethyl)-2-[7-(2-amino-2-carboxyethyl)-5-oxo-5H-1,4-benzothiazin-2-yl]-5-hydroxy-4H-1,4-benzothiazine-3-carboxylic acid
化学式: C23H20N4O8S2 (544.0723)
中文名称:
谱图信息:
最多检出来源 Rattus norvegicus(not specific) 1.09%
分子结构信息
SMILES: C1=C(C=C2C(=C1O)NC(=C(S2)C3=CN=C4C(=CC(=CC4=O)CC(C(=O)O)N)S3)C(=O)O)CC(C(=O)O)N
InChI: InChI=1S/C23H20N4O8S2/c24-10(21(30)31)1-8-3-12(28)17-14(5-8)36-16(7-26-17)20-19(23(34)35)27-18-13(29)4-9(6-15(18)37-20)2-11(25)22(32)33/h3-7,10-11,27,29H,1-2,24-25H2,(H,30,31)(H,32,33)(H,34,35)
描述信息
同义名列表
5 个代谢物同义名
7-(2-amino-2-carboxyethyl)-2-[7-(2-amino-2-carboxyethyl)-5-oxo-5H-1,4-benzothiazin-2-yl]-5-hydroxy-4H-1,4-benzothiazine-3-carboxylic acid; 7-(2-amino-2-carboxyethyl)-2-[7-(2-amino-2-carboxyethyl)-5-oxo-1,4-benzothiazin-2-yl]-5-hydroxy-4H-1,4-benzothiazine-3-carboxylic acid; Trichochrome F; Eumelanins; Eumelanin
相关代谢途径
Reactome()
BioCyc()
PlantCyc()
代谢反应
个相关的代谢反应过程信息。
Reactome()
BioCyc()
WikiPathways()
Plant Reactome()
INOH()
PlantCyc()
COVID-19 Disease Map()
PathBank()
PharmGKB()
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 |
|---|
文献列表
- Wen Song, Ronge Xing, Haoyue Yang, Song Liu, Huahua Yu, Pengcheng Li. Therapeutic potential of enzymatically extracted eumelanin from squid ink in type 2 diabetes mellitus ICR mice: Multifaceted intervention against hyperglycemia, oxidative stress and depression.
Journal of the science of food and agriculture.
2024 Jan; 104(2):993-1007. doi:
10.1002/jsfa.12986. [PMID: 37715565] - Silvia Yunmam, Hae Ran Lee, Seong Min Hong, Ji-Young Kim, Tong Ho Kang, Ai Young Lee, Dae Sik Jang, Sun Yeou Kim. Aspacochioside C from Asparagus cochinchinensis attenuates eumelanin synthesis via inhibition of TRP2 expression.
Scientific reports.
2023 09; 13(1):14831. doi:
10.1038/s41598-023-41248-5. [PMID: 37684311] - Rita Argenziano, Maria Laura Alfieri, Noemi Gallucci, Gerardino D'Errico, Lucia Panzella, Alessandra Napolitano. A Model Eumelanin from 5,6-Dihydroxyindole-2-Carboxybutanamide Combining Remarkable Antioxidant and Photoprotective Properties with a Favourable Solubility Profile for Dermo-Cosmetic Applications.
International journal of molecular sciences.
2023 Feb; 24(4):. doi:
10.3390/ijms24044241. [PMID: 36835650] - Minkyung Kim, Kyungeun Jeon, Seoungwoo Shin, Sohyun Yoon, Hayeon Kim, Hee Young Kang, Dehun Ryu, Deokhoon Park, Eunsun Jung. Melanogenesis-promoting effect of Cirsium japonicum flower extract in vitro and ex vivo.
International journal of cosmetic science.
2021 Dec; 43(6):703-714. doi:
10.1111/ics.12746. [PMID: 34674286] - Ruth Edge, T George Truscott. COVID-19 and the ethnicity link - is there a photochemical link?.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.
2021 Jan; 20(1):183-188. doi:
10.1007/s43630-020-00004-8. [PMID: 33721239] - Sameh S M Soliman, Rania Hamdy, Samia A Elseginy, Teclegiorgis Gebremariam, Alshaimaa M Hamoda, Mohamed Madkour, Thenmozhi Venkatachalam, Mai N Ershaid, Mohammad G Mohammad, Georgios Chamilos, Ashraf S Ibrahim. Selective inhibition of Rhizopus eumelanin biosynthesis by novel natural product scaffold-based designs caused significant inhibition of fungal pathogenesis.
The Biochemical journal.
2020 07; 477(13):2489-2507. doi:
10.1042/bcj20200310. [PMID: 32538426] - Jacqueline Knaust, Rosemarie Weikard, Elke Albrecht, Ronald M Brunner, Juliane Günther, Christa Kühn. Indication of Premelanosome Protein (PMEL) Expression Outside of Pigmented Bovine Skin Suggests Functions Beyond Eumelanogenesis.
Genes.
2020 07; 11(7):. doi:
10.3390/genes11070788. [PMID: 32668786] - Chie Miyabe, Yupeng Dong, Kazumasa Wakamatsu, Shosuke Ito, Tamihiro Kawakami. Kojic acid alters pheomelanin content in human induced pluripotent stem cell-derived melanocytes.
The Journal of dermatology.
2020 Apr; 47(4):435-436. doi:
10.1111/1346-8138.15260. [PMID: 32067265] - María Del Rosario Gil-Avilés, Julio Montes-Avila, Sylvia Páz Díaz-Camacho, Manuel Adrián Picos-Salas, Gabriela López-Angulo, Edgar Alonso Reynoso-Soto, Lorenzo Ulises Osuna-Martínez, Francisco Delgado-Vargas. Soluble melanins of the Randia echinocarpa fruit - Structural characteristics and toxicity.
Journal of food biochemistry.
2019 12; 43(12):e13077. doi:
10.1111/jfbc.13077. [PMID: 31608463] - Johan Lindgren, Peter Sjövall, Volker Thiel, Wenxia Zheng, Shosuke Ito, Kazumasa Wakamatsu, Rolf Hauff, Benjamin P Kear, Anders Engdahl, Carl Alwmark, Mats E Eriksson, Martin Jarenmark, Sven Sachs, Per E Ahlberg, Federica Marone, Takeo Kuriyama, Ola Gustafsson, Per Malmberg, Aurélien Thomen, Irene Rodríguez-Meizoso, Per Uvdal, Makoto Ojika, Mary H Schweitzer. Soft-tissue evidence for homeothermy and crypsis in a Jurassic ichthyosaur.
Nature.
2018 12; 564(7736):359-365. doi:
10.1038/s41586-018-0775-x. [PMID: 30518862] - Raffaella Micillo, Mariagrazia Iacomino, Marco Perfetti, Lucia Panzella, Kenzo Koike, Gerardino D'Errico, Marco d'Ischia, Alessandra Napolitano. Unexpected impact of esterification on the antioxidant activity and (photo)stability of a eumelanin from 5,6-dihydroxyindole-2-carboxylic acid.
Pigment cell & melanoma research.
2018 07; 31(4):475-483. doi:
10.1111/pcmr.12689. [PMID: 29350885] - Subhasish Chatterjee, Rafael Prados-Rosales, Boris Itin, Arturo Casadevall, Ruth E Stark. Solid-state NMR Reveals the Carbon-based Molecular Architecture of Cryptococcus neoformans Fungal Eumelanins in the Cell Wall.
The Journal of biological chemistry.
2015 May; 290(22):13779-90. doi:
10.1074/jbc.m114.618389. [PMID: 25825492] - Armelle Chassepot, Vincent Ball. Human serum albumin and other proteins as templating agents for the synthesis of nanosized dopamine-eumelanin.
Journal of colloid and interface science.
2014 Jan; 414(?):97-102. doi:
10.1016/j.jcis.2013.10.002. [PMID: 24231090] - Ismael Galván, Carlos Alonso-Alvarez, Juan J Negro. Relationships between hair melanization, glutathione levels, and senescence in wild boars.
Physiological and biochemical zoology : PBZ.
2012 Jul; 85(4):332-47. doi:
10.1086/666606. [PMID: 22705484] - Tomohisa Hirobe, Chihiro Yoshihara, Sakae Takeuchi, Kazumasa Wakamatsu, Shosuke Ito, Hiroyuki Abe, Yoko Kawa, Yoshinao Soma. A novel deletion mutation of mouse ruby-eye 2 named ru2(d)/Hps5(ru2-d) inhibits melanocyte differentiation and its impaired differentiation is rescued by L-tyrosine.
Zoological science.
2011 Nov; 28(11):790-801. doi:
10.2108/zsj.28.790. [PMID: 22035301] - Hiroaki Nakajima, Yuki Wakabayashi, Kazumasa Wakamatsu, Genji Imokawa. An extract of Withania somnifera attenuates endothelin-1-stimulated pigmentation in human epidermal equivalents through the interruption of PKC activity within melanocytes.
Phytotherapy research : PTR.
2011 Sep; 25(9):1398-411. doi:
10.1002/ptr.3552. [PMID: 21678520] - Hiroaki Nakajima, Yuki Wakabayashi, Kazumasa Wakamatsu, Genji Imokawa. An extract of Melia toosendan attenuates endothelin-1-stimulated pigmentation in human epidermal equivalents through the interruption of PKC activity within melanocytes.
Archives of dermatological research.
2011 May; 303(4):263-76. doi:
10.1007/s00403-011-1143-y. [PMID: 21442473] - Jacoba E Smit, Anne F Grobler, Raymond W Sparrow. Influence of variation in eumelanin content on absorbance spectra of liquid skin-like phantoms.
Photochemistry and photobiology.
2011 Jan; 87(1):64-71. doi:
10.1111/j.1751-1097.2010.00824.x. [PMID: 21073475] - Ayako Kumagai, Nanao Horike, Yudai Satoh, Tatsuya Uebi, Tsutomu Sasaki, Yumi Itoh, Yoshiyuki Hirata, Kozue Uchio-Yamada, Kazuo Kitagawa, Shinichi Uesato, Hidehisa Kawahara, Hiroshi Takemori, Yasuo Nagaoka. A potent inhibitor of SIK2, 3, 3', 7-trihydroxy-4'-methoxyflavon (4'-O-methylfisetin), promotes melanogenesis in B16F10 melanoma cells.
PloS one.
2011; 6(10):e26148. doi:
10.1371/journal.pone.0026148. [PMID: 22022544] - Wirginia Krzyściak. Activity of selected aromatic amino acids in biological systems.
Acta biochimica Polonica.
2011; 58(4):461-6. doi:
10.18388/abp.2011_2211. [PMID: 22175049] - A Bennett, V Hayssen. Measuring cortisol in hair and saliva from dogs: coat color and pigment differences.
Domestic animal endocrinology.
2010 Oct; 39(3):171-80. doi:
10.1016/j.domaniend.2010.04.003. [PMID: 20705413] - Ryan P McGlinchey, Frank Shewmaker, Peter McPhie, Begoña Monterroso, Kent Thurber, Reed B Wickner. The repeat domain of the melanosome fibril protein Pmel17 forms the amyloid core promoting melanin synthesis.
Proceedings of the National Academy of Sciences of the United States of America.
2009 Aug; 106(33):13731-6. doi:
10.1073/pnas.0906509106. [PMID: 19666488] - Dzeneta Nezirević, Kerstin Arstrand, Bertil Kågedal. Hydrophilic interaction liquid chromatographic analysis of aminohydroxyphenylalanines from melanin pigments.
Journal of chromatography. A.
2007 Sep; 1163(1-2):70-9. doi:
10.1016/j.chroma.2007.06.007. [PMID: 17588592] - Tomohisa Hirobe, Hiyoyuki Abe, Kazumasa Wakamatsu, Shosuke Ito, Yoko Kawa, Yoshinao Soma, Masako Mizoguchi. Excess tyrosine rescues the reduced activity of proliferation and differentiation of cultured recessive yellow melanocytes derived from neonatal mouse epidermis.
European journal of cell biology.
2007 Jun; 86(6):315-30. doi:
10.1016/j.ejcb.2007.03.007. [PMID: 17532540] - Tomohisa Hirobe, Kazumasa Wakamatsu, Shosuke Ito. Excess tyrosine stimulates eumelanin and pheomelanin synthesis in cultured slaty melanocytes from neonatal mouse epidermis.
Zoological science.
2007 Mar; 24(3):209-17. doi:
10.2108/zsj.24.209. [PMID: 17551240] - Kazutaka Murakami, Kazumasa Wakamatsu, Yukiko Nakanishi, Hiroki Takahashi, Satoshi Sugiyama, Shosuke Ito. Serum levels of pigmentation markers are elevated in patients undergoing hemodialysis.
Blood purification.
2007; 25(5-6):483-9. doi:
10.1159/000112516. [PMID: 18089933] - V H Lagunas-Muñoz, N Cabrera-Valladares, F Bolívar, G Gosset, A Martínez. Optimum melanin production using recombinant Escherichia coli.
Journal of applied microbiology.
2006 Nov; 101(5):1002-8. doi:
10.1111/j.1365-2672.2006.03013.x. [PMID: 17040223] - Kazumasa Wakamatsu, Akihiko Takasaki, Bertil Kågedal, Toshiro Kageshita, Shosuke Ito. Determination of eumelanin in human urine.
Pigment cell research.
2006 Apr; 19(2):163-9. doi:
10.1111/j.1600-0749.2006.00296.x. [PMID: 16524432] - Tomohisa Hirobe, Kazumasa Wakamatsu, Shosuke Ito. Changes in the proliferation and differentiation of neonatal mouse pink-eyed dilution melanocytes in the presence of excess tyrosine.
Pigment cell research.
2003 Dec; 16(6):619-28. doi:
10.1046/j.1600-0749.2003.00091.x. [PMID: 14629719] - Shosuke Ito, Kazumasa Wakamatsu. Quantitative analysis of eumelanin and pheomelanin in humans, mice, and other animals: a comparative review.
Pigment cell research.
2003 Oct; 16(5):523-31. doi:
10.1034/j.1600-0749.2003.00072.x. [PMID: 12950732] - A Cherqui, B Duvic, C Reibel, M Brehélin. Cooperation of dopachrome conversion factor with phenoloxidase in the eumelanin pathway in haemolymph of Locusta migratoria (Insecta).
Insect biochemistry and molecular biology.
1998 Nov; 28(11):839-48. doi:
10.1016/s0965-1748(98)00076-9. [PMID: 9818385] - K A Miller, T M Gunn, M M Carrasquillo, M L Lamoreux, D B Galbraith, G S Barsh. Genetic studies of the mouse mutations mahogany and mahoganoid.
Genetics.
1997 Aug; 146(4):1407-15. doi:
10.1093/genetics/146.4.1407. [PMID: 9258683] - G Sjölin-Forsberg, C Hansson, B Kågedal, E L Gannedahl, B Berne. Urinary excretion of melanocyte metabolites during treatment with chloroquine phosphate.
Acta dermato-venereologica.
1995 Jul; 75(4):287-9. doi:
10.2340/0001555575287289. [PMID: 8578950] - S Schmitz, P D Thomas, T M Allen, M J Poznansky, K Jimbow. Dual role of melanins and melanin precursors as photoprotective and phototoxic agents: inhibition of ultraviolet radiation-induced lipid peroxidation.
Photochemistry and photobiology.
1995 Jun; 61(6):650-5. doi:
10.1111/j.1751-1097.1995.tb09883.x. [PMID: 7568412] - N D Charalambidis, S N Bournazos, M Lambropoulou, V J Marmaras. Defense and melanization depend on the eumelanin pathway, occur independently and are controlled differentially in developing Ceratitis capitata.
Insect biochemistry and molecular biology.
1994 Jul; 24(7):655-62. doi:
10.1016/0965-1748(94)90052-3. [PMID: 8069330] - H Hara, N Walsh, K Yamada, K Jimbow. High plasma level of a eumelanin precursor, 6-hydroxy-5-methoxyindole-2-carboxylic acid as a prognostic marker for malignant melanoma.
The Journal of investigative dermatology.
1994 Apr; 102(4):501-5. doi:
10.1111/1523-1747.ep12373153. [PMID: 8151128] - B Matous, E Bubnova, A Budesinska, M Kostirova. Markers of melanogenesis in malignant melanoma.
Sbornik lekarsky.
1994; 95(4):333-38. doi:
NULL. [PMID: 8867704] - Y Tomita, Y Kondo, S Ito, M Hara, T Yoshimura, H Igarashi, H Tagami. Menkes' disease: report of a case and determination of eumelanin and pheomelanin in hypopigmented hair.
Dermatology (Basel, Switzerland).
1992; 185(1):66-8. doi:
10.1159/000247407. [PMID: 1638075] - N Saito, T Morishima. Eumelanin and pheomelanin contents in hair and 5-S-cysteinyldopa and 5-hydroxy-6-methoxyindole-2-carboxylic acid levels in urine in Japanese oculocutaneous albinism.
Archives of dermatological research.
1991; 283(1):7-9. doi:
10.1007/bf01207242. [PMID: 2059060] - N Saito, T Morishima. [Eumelanin and pheomelanin contents in hairs of healthy Japanese and patients with oculocutaneous albinism, and 5-S-cysteinyldopa and 5-hydroxy-6-methoxyindole-2-carboxylic acid levels in urine of oculocutaneous albinism].
Nihon Hifuka Gakkai zasshi. The Japanese journal of dermatology.
1990 Jul; 100(8):853-61. doi:
NULL. [PMID: 2122048] - E Bubnová, A Budĕsínská, Z Schwippelová, B Matous, T Trnka. [Synthesis of eumelanin pigment precursors. II. 6-hydroxy-5-methoxy- and 5-hydroxy-6- methoxyindole].
Sbornik lekarsky.
1989 Sep; 91(8-9):225-9. doi:
NULL. [PMID: 2562578] - E Bubnová, A Budĕsínská, Z Schwippelová, B Matous, T Trnka. [Synthesis of eumelanin pigment precursors. II. 6-Hydroxy-5-methoxy- and 5-hydroxy-6-methoxyindol].
Sbornik lekarsky.
1989 Sep; 91(8):225-9. doi:
NULL. [PMID: 2617122] - S Ito, K Wakamatsu. Melanin chemistry and melanin precursors in melanoma.
The Journal of investigative dermatology.
1989 May; 92(5 Suppl):261S-265S. doi:
10.1111/1523-1747.ep13076587. [PMID: 2654299] - K Wakamatsu, S Ito. Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and their O-methyl derivatives.
Analytical biochemistry.
1988 May; 170(2):335-40. doi:
10.1016/0003-2697(88)90639-2. [PMID: 3394933] - S A Burchill, A J Thody, S Ito. Melanocyte-stimulating hormone, tyrosinase activity and the regulation of eumelanogenesis and phaeomelanogenesis in the hair follicular melanocytes of the mouse.
The Journal of endocrinology.
1986 Apr; 109(1):15-21. doi:
10.1677/joe.0.1090015. [PMID: 3084696] - S Pavel, W van der Slik. Analysis of eumelanin-related indolic compounds in urine by high-performance liquid chromatography with fluorimetric detection.
Journal of chromatography.
1986 Mar; 375(2):392-8. doi:
10.1016/s0378-4347(00)83733-0. [PMID: 2422190] - S Pavel, H Elzinga, F A Muskiet, J M Smit, N H Mulder, H S Koops. Eumelanin-related indolic compounds in the urine of treated melanoma patients.
Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie.
1986 Mar; 24(3):167-73. doi:
10.1515/cclm.1986.24.3.167. [PMID: 3711799]
