Ascomycin (BioDeep_00000009096)

 

Secondary id: BioDeep_00000176252

Chemicals and Drugs natural product


代谢物信息卡片


(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R ,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,1 9,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E )-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetrameth yl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone

化学式: C43H69NO12 (791.4819514)
中文名称: 长川霉素, 子囊霉素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.87%

分子结构信息

SMILES: CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC
InChI: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+

描述信息

Ascomycin is a macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties. It has a role as an immunosuppressive agent, an antifungal agent and a bacterial metabolite. It is a macrolide, an ether, a lactol and a secondary alcohol.
Ascomycin is a natural product found in Streptomyces clavuligerus, Streptomyces hygroscopicus, and Streptomyces ascomycinicus with data available.
A macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties.
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
Ascomycin (Immunomycin; FR-900520; FK520) is an ethyl analog of Tacrolimus (FK506) with strong immunosuppressant properties. Ascomycin is also a macrocyclic polyketide antibiotic with multiple biological activities such as anti-malarial, anti-fungal and anti-spasmodic. Ascomycin prevents graft rejection and has potential for varying skin ailments research[1][2].

同义名列表

31 个代谢物同义名

(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R ,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,1 9,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E )-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetrameth yl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,22R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone; 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-8-ethyl-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S-(3R*(E(1S*,3S*,4S*)),4S*,19S*,26aR*))-; (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-Hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone; (E)-(9S,12S,13R,14S,17R,21S,23S,24R,25S,27S)-17-Ethyl-1,14-dihydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone; (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0?,?]octacos-18-ene-2,3,10,16-tetrone; 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetram; (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone; (E)-(S)-17-Ethyl-1,14-dihydroxy-12-[(E)-2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]oct acos-18-ene-2,3,10,16-tetraone; (ascomycin)17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone; (E)-17-Ethyl-1,14-dihydroxy-12-[(E)-2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone; 17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone; Ascomycin from Streptomyces hygroscopicus var. ascomyceticus; TACROLIMUS MONOHYDRATE IMPURITY A [EP IMPURITY]; TACROLIMUS IMPURITY, ASCOMYCIN- [USP IMPURITY]; tacrolimus related compound A; ZDQSOHOQTUFQEM-NURRSENYSA-N; UNII-AUF4U5NSJK; changchuanmycin; IDI1_033788; immunomycin; C43H69NO12; AUF4U5NSJK; Ascomycin; FK520; Ascomycin, Streptomyces hygroscopicus; Ascomycin (Immunomycin,FK-520); FR-900520; Immunomycin



数据库引用编号

30 个数据库交叉引用编号

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代谢反应

0 个相关的代谢反应过程信息。

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14 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

  • Jason A Justice, Anthony J Schulien, Kai He, Karen A Hartnett, Elias Aizenman, Niyathi H Shah. Disruption of KV2.1 somato-dendritic clusters prevents the apoptogenic increase of potassium currents. Neuroscience. 2017 06; 354(?):158-167. doi: 10.1016/j.neuroscience.2017.04.034. [PMID: 28461216]
  • Bernhard F Gibbs, Inna M Yasinska, Luigi Calzolai, Douglas Gilliland, Vadim V Sumbayev. Highly specific targeting of human leukocytes using gold nanoparticle-based biologically active conjugates. Journal of biomedical nanotechnology. 2014 Jul; 10(7):1259-66. doi: 10.1166/jbn.2014.1807. [PMID: 24804546]
  • Heike Burhenne, Jan T Kielstein, Olaf Burkhardt, Volkhard Kaever. Quantitative analysis of the antifungal drug anidulafungin by LC-online SPE-MS/MS in human plasma. Biomedical chromatography : BMC. 2012 Jun; 26(6):681-3. doi: 10.1002/bmc.1732. [PMID: 22020627]
  • Xiao-ling Qin, Hui-chang Bi, Chang-xi Wang, Jia-li Li, Xue-ding Wang, Long-shan Liu, Xiao Chen, Min Huang. Study of the effect of Wuzhi tablet (Schisandra sphenanthera extract) on tacrolimus tissue distribution in rat by liquid chromatography tandem mass spectrometry method. Biomedical chromatography : BMC. 2010 Apr; 24(4):399-405. doi: 10.1002/bmc.1305. [PMID: 19693766]
  • A M Marsland, S Soundararajan, K Joseph, A P Kaplan. Effects of calcineurin inhibitors on an in vitro assay for chronic urticaria. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology. 2005 May; 35(5):554-9. doi: 10.1111/j.1365-2222.2005.02242.x. [PMID: 15898974]
  • Aaron P Jansen, Corinne E Camalier, Cristi Stark, Nancy H Colburn. Characterization of programmed cell death 4 in multiple human cancers reveals a novel enhancer of drug sensitivity. Molecular cancer therapeutics. 2004 Feb; 3(2):103-10. doi: NULL. [PMID: 14985450]
  • Marcie Colledge, Eric M Snyder, Robert A Crozier, Jacquelyn A Soderling, Yetao Jin, Lorene K Langeberg, Hua Lu, Mark F Bear, John D Scott. Ubiquitination regulates PSD-95 degradation and AMPA receptor surface expression. Neuron. 2003 Oct; 40(3):595-607. doi: 10.1016/s0896-6273(03)00687-1. [PMID: 14642282]
  • K England, J Watson, G Beale, M Warner, J Cross, M Rumsby. Signalling pathways regulating the dephosphorylation of Ser729 in the hydrophobic domain of protein kinase Cepsilon upon cell passage. The Journal of biological chemistry. 2001 Mar; 276(13):10437-42. doi: 10.1074/jbc.m009421200. [PMID: 11121415]
  • U Holtbäck, A C Eklöf. Mechanism of FK 506/520 action on rat renal proximal tubular Na+, K+-ATPase activity. Kidney international. 1999 Sep; 56(3):1014-21. doi: 10.1046/j.1523-1755.1999.00620.x. [PMID: 10469369]
  • H M Armstrong, F Wong, M A Holmes, P J Sinclair, M T Goulet, F J Dumont, M J Staruch, S Koprak, L B Peterson, R Rosa, M B Wilusz, G J Wiederrecht, J G Cryan, M J Wyvratt, W H Parsons. Potent immunosuppressive C32-O-arylethyl ether derivatives of ascomycin with reduced toxicity. Bioorganic & medicinal chemistry letters. 1999 Jul; 9(14):2089-94. doi: 10.1016/s0960-894x(99)00336-4. [PMID: 10450987]
  • M T Goulet, S R McAlpine, M J Staruch, S Koprak, F J Dumont, J G Cryan, G J Wiederrecht, R Rosa, M B Wilusz, L B Peterson, M J Wyvratt, W H Parsons. C32-O-imidazol-2-yl-methyl ether derivatives of the immunosuppressant ascomycin with improved therapeutic potential. Bioorganic & medicinal chemistry letters. 1998 Aug; 8(16):2253-8. doi: 10.1016/s0960-894x(98)00397-7. [PMID: 9873523]
  • K W Mollison, T A Fey, R A Krause, J M Andrews, P T Bretheim, P K Cusick, G C Hsieh, J R Luly. Nephrotoxicity studies of the immunosuppressants tacrolimus (FK506) and ascomycin in rat models. Toxicology. 1998 Feb; 125(2-3):169-81. doi: 10.1016/s0300-483x(97)00167-4. [PMID: 9570331]
  • K W Mollison, T A Fey, R A Krause, J M Andrews, P T Bretheim, J A Brandt, M Kawai, R Wagner, G C Hsieh, J R Luly. Discovery of less nephrotoxic FK506 analogs and determining immunophilin dependence of immunosuppressant nephrotoxicity with a novel single-dose rat cisplatin potentiation assay. The Journal of pharmacology and experimental therapeutics. 1997 Dec; 283(3):1509-19. doi: . [PMID: 9400028]
  • R Bakhtiar, R A Stearns. Studies on non-covalent associations of immunosuppressive drugs with serum albumin using pneumatically assisted electrospray ionization mass spectrometry. Rapid communications in mass spectrometry : RCM. 1995; 9(3):240-4. doi: 10.1002/rcm.1290090313. [PMID: 7535601]
  • S H Vincent, R W Wang, B V Karanam, M Klimko, R Alvaro, S H Chiu. Effects of the immunosuppressant FK-506 and its analog FK-520 on hepatic and renal cytochrome P450 mixed-function oxidase. Biochemical pharmacology. 1991 May; 41(9):1325-30. doi: 10.1016/0006-2952(91)90104-d. [PMID: 1708254]
  • F P Gailliot, C Gleason, J J Wilson, J Zwarick. Fluidized bed adsorption for whole broth extraction. Biotechnology progress. 1990 Sep; 6(5):370-5. doi: 10.1021/bp00005a009. [PMID: 1366874]