Tuberculostearic acid (BioDeep_00000011410)

 

Secondary id: BioDeep_00001872001

human metabolite Endogenous Volatile Flavor Compounds natural product


代谢物信息卡片


10R-methyl-octadecanoic acid

化学式: C19H38O2 (298.28716479999997)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 8.7%

分子结构信息

SMILES: C(CCCCCCCCC(C)CCCCCCCC)(=O)O
InChI: InChI=1S/C19H38O2/c1-3-4-5-6-9-12-15-18(2)16-13-10-7-8-11-14-17-19(20)21/h18H,3-17H2,1-2H3,(H,20,21)

描述信息

Tuberculostearic acid is the characteristic fatty acid of acid-fast bacteria of the order Actinomycetales. (PMID 3329256). Tuberculostearic acid (TBSA) is a mycobacterial cell wall constituent that is possible to measure in plasma samples of patients with active tuberculosis. (PMID 14723350). Detection of tuberculostearic acid in cerebrospinal fluid by use of gas chromatography-mass spectrometry has proven to be a very rapid, sensitive, and specific test for tuberculous meningitis. (PMID 8438134). Tuberculostearic acid can also be found in Actinomycetales (PMID: 109465).
Tuberculostearic acid is the characteristic fatty acid of acid-fast bacteria of the order Actinomycetales. (PMID 3329256)

同义名列表

13 个代谢物同义名

10R-methyl-octadecanoic acid; L-(+)-Tuberculostearic acid; 10-methyl-octadecanoic acid; 10-Methyloctadecanoic acid; 10-Methyl-octadecanoate; 10-Methyloctadecanoate; 10-methyl-stearic acid; Tuberculostearic acid; 10-methylstearic acid; Tuberculostearate; 10-Methylstearate; FA 19:0; Tuberculostearic acid



数据库引用编号

16 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)

15 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

  • Malavika Prithviraj, Takehiro Kado, Jacob A Mayfield, David C Young, Annie D Huang, Daisuke Motooka, Shota Nakamura, M Sloan Siegrist, D Branch Moody, Yasu S Morita. Tuberculostearic Acid Controls Mycobacterial Membrane Compartmentalization. mBio. 2023 Mar; ?(?):e0339622. doi: 10.1128/mbio.03396-22. [PMID: 36976029]
  • Julius Brandenburg, Jan Heyckendorf, Franziska Marwitz, Nicole Zehethofer, Lara Linnemann, Nicolas Gisch, Hande Karaköse, Maja Reimann, Katharina Kranzer, Barbara Kalsdorf, Patricia Sanchez-Carballo, Michael Weinkauf, Verena Scholz, Sven Malm, Susanne Homolka, Karoline I Gaede, Christian Herzmann, Ulrich E Schaible, Christoph Hölscher, Norbert Reiling, Dominik Schwudke. Tuberculostearic Acid-Containing Phosphatidylinositols as Markers of Bacterial Burden in Tuberculosis. ACS infectious diseases. 2022 07; 8(7):1303-1315. doi: 10.1021/acsinfecdis.2c00075. [PMID: 35763439]
  • Pratap S Patil, Ting-Jen Rachel Cheng, Medel Manuel L Zulueta, Shih-Ting Yang, Larry S Lico, Shang-Cheng Hung. Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity. Nature communications. 2015 Jun; 6(?):7239. doi: 10.1038/ncomms8239. [PMID: 26037164]
  • Ngoc A Dang, Hans-Gerd Janssen, Arend H J Kolk. Rapid diagnosis of TB using GC-MS and chemometrics. Bioanalysis. 2013 Dec; 5(24):3079-97. doi: 10.4155/bio.13.288. [PMID: 24320132]
  • Laxman S Meena, Pappachan E Kolattukudy. Expression and characterization of Rv0447c product, potentially the methyltransferase involved in tuberculostearic acid biosynthesis in Mycobacterium tuberculosis. Biotechnology and applied biochemistry. 2013 Jul; 60(4):412-6. doi: 10.1002/bab.1112. [PMID: 24033595]
  • Soon Dong Lee, Se Jae Kim. Aeromicrobium tamlense sp. nov., isolated from dried seaweed. International journal of systematic and evolutionary microbiology. 2007 Feb; 57(Pt 2):337-341. doi: 10.1099/ijs.0.64442-0. [PMID: 17267975]
  • G L Daikos, J B Brooks, A Michos, E Roma, V Syriopoulou. Detection of tuberculostearic acid in serum and other biological fluids from patients with tuberculosis by electron capture-gas chromatography and chemical ionisation-mass spectrometry. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease. 2004 Aug; 8(8):1027-31. doi: . [PMID: 15305489]
  • Friederike Traunmüller, Markus Alexander Zeitlinger, Brigitte Stoiser, Heimo Lagler, Haider Abdulla Abdel Salam, Elisabeth Presterl, Wolfgang Graninger. Circulating tuberculostearic acid in tuberculosis patients. Scandinavian journal of infectious diseases. 2003; 35(11-12):790-3. doi: 10.1080/00365540310017032. [PMID: 14723350]
  • V Syriopoulou, J B Brooks, G L Daikos. Electron-capture gas chromatographic-chemical ionization mass spectrometric study of sera from people vaccinated with bacille Calmette-Guerin for characteristic metabolites. Journal of chromatography. B, Biomedical sciences and applications. 2001 Feb; 751(1):143-51. doi: 10.1016/s0378-4347(00)00465-5. [PMID: 11232844]
  • J B Brooks, V Syriopoulou, W R Butler, G Saroglow, K Karydis, P L Almenoff. Development of a quantitative chemical ionization gas chromatography-mass spectrometry method to detect tuberculostearic acid in body fluids. Journal of chromatography. B, Biomedical sciences and applications. 1998 Aug; 712(1-2):1-10. doi: 10.1016/s0378-4347(98)00158-3. [PMID: 9698223]
  • J Nigou, M Gilleron, B Cahuzac, J D Bounéry, M Herold, M Thurnher, G Puzo. The phosphatidyl-myo-inositol anchor of the lipoarabinomannans from Mycobacterium bovis bacillus Calmette Guérin. Heterogeneity, structure, and role in the regulation of cytokine secretion. The Journal of biological chemistry. 1997 Sep; 272(37):23094-103. doi: 10.1074/jbc.272.37.23094. [PMID: 9287310]
  • P L Almenoff, J B Brooks, A Johnson, M Lesser. Differentiation of sarcoidosis from tuberculosis by use of electron capture gas-liquid chromatography. Lung. 1996; 174(6):349-58. doi: 10.1007/bf00164632. [PMID: 8887930]
  • C Gailly, F David, P Sandra, M A Laneelle, C Cocito. Lipid composition of leprosy-derived corynebacteria, a distinct group of corynebacteria, and of a reference Corynebacterium. Biotechnology therapeutics. 1993; 4(1-2):99-116. doi: . [PMID: 8374515]
  • A N Chakrabarty, S G Dastidar. Leprosy-derived chemoautotrophic nocardioform (CAN) bacteria closely resemble, or are identical with, Mycobacterium leprae on mycolate and other lipid profiles. Indian journal of leprosy. 1992 Oct; 64(4):529-35. doi: ". [PMID: 1308529]
  • V Ausina, M Luquin, M García Barceló, M A Lanéelle, V Lévy-Frébault, F Belda, G Prats. Mycobacterium alvei sp. nov. International journal of systematic bacteriology. 1992 Oct; 42(4):529-35. doi: 10.1099/00207713-42-4-529. [PMID: 1390105]
  • H Muranishi, M Nakashima, T Ando, N Shigematsu, R Isobe. [Basic and clinical evaluation of rapid diagnosis of tuberculosis by detecting tuberculostearic acid]. Kekkaku : [Tuberculosis]. 1990 Jan; 65(1):39-42. doi: . [PMID: 2313961]
  • J Elias, J P De Coning, S A Vorster, H F Joubert. The rapid and sensitive diagnosis of tuberculous meningitis by the detection of tuberculostearic acid in cerebrospinal fluid using gas chromatography-mass spectrometry with selective ion monitoring. Clinical biochemistry. 1989 Dec; 22(6):463-7. doi: 10.1016/s0009-9120(89)80099-2. [PMID: 2611993]
  • L Larsson, J Jimenez, A Sonesson, F Portaels. Two-dimensional gas chromatography with electron capture detection for the sensitive determination of specific mycobacterial lipid constituents. Journal of clinical microbiology. 1989 Oct; 27(10):2230-3. doi: 10.1128/jcm.27.10.2230-2233.1989. [PMID: 2685023]
  • J B Brooks, M I Daneshvar, D M Fast, R C Good. Selective procedures for detecting femtomole quantities of tuberculostearic acid in serum and cerebrospinal fluid by frequency-pulsed electron capture gas-liquid chromatography. Journal of clinical microbiology. 1987 Jul; 25(7):1201-6. doi: 10.1128/jcm.25.7.1201-1206.1987. [PMID: 3611313]
  • J B Brooks, J V Kasin, D M Fast, M I Daneshvar. Detection of metabolites by frequency-pulsed electron capture gas-liquid chromatography in serum and cerebrospinal fluid of a patient with Nocardia infection. Journal of clinical microbiology. 1987 Feb; 25(2):445-8. doi: 10.1128/jcm.25.2.445-448.1987. [PMID: 3818936]