gosspyl acetate (BioDeep_00000230451)

 

Secondary id: BioDeep_00000395715

PANOMIX_OTCML-2023


代谢物信息卡片


acetic acid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

化学式: C30H30O8.C2H4O2 (578.2151864)
中文名称: 醋酸棉酚
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.9%

分子结构信息

SMILES: CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O.CC(=O)O
InChI: 1H3,(H,3,4)

描述信息

R-(-)-Gossypol Acetic Acid is the orally bioavailable solvate of the R-(-) enantiomer of gossypol and acetic acid with potential antineoplastic activity. As a BH3 mimetic, R-(-)-gossypol binds to the hydrophobic surface binding groove BH3 of the anti-apoptotic proteins Bcl-2 and Bcl-xL, blocking their heterodimerization with pro-apoptotic members of the Bcl-2 family of proteins such as Bad, Bid, and Bim; this may result in the inhibition of tumor cell proliferation and the induction of tumor cell apoptosis. Racemic gossypol is a polyphenolic compound isolated from cottonseed.
Gossypol acetic acid ((±)-Gossypol-acetic acid) binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.
Gossypol acetic acid ((±)-Gossypol-acetic acid) binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.

同义名列表

41 个代谢物同义名

acetic acid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde; aceticacid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde; acetic acid compound with (S)-1,1,6,6,7,7-hexahydroxy-5,5-diisopropyl-3,3-dimethyl-[2,2-binaphthalene]-8,8-dicarbaldehyde (1:1); Acetic acid compound with 1,1,6,6,7,7-hexahydroxy-5,5-diisopropyl-3,3-dimethyl-[2,2-binaphthalene]-8,8-dicarbaldehyde (1:1); acetic acid compound with 1,1,6,6,7,7-hexahydroxy-5,5-diisopropyl-3,3-dimethyl-2,2-binaphthyl-8,8-dicarbaldehyde (1:1); Acetic acid--1,1,6,6,7,7-hexahydroxy-3,3-dimethyl-5,5-di(propan-2-yl)[2,2-binaphthalene]-8,8-dicarbaldehyde (1/1); 1,1,6,6,7,7-Hexahydroxy-5,5-diisopropyl-3,3-dimethyl-2,2-binaphthalene-8,8-dicarbaldehyde - acetic acid (1:1); 1,1,6,6,7,7-Hexahydroxy-5,5-diisopropyl-3,3-dimethyl-[2,2-binaphthalene]-8,8-dicarbaldehyde acetate salt; ( inverted exclamation markA)-Gossypol-acetic acid; Gossypol acetic acid clathrate; Gossypol acetic acid [WHO-DD]; (S)-Gossypol acetic acid salt; (R)-Gossypol acetic acid salt; (R)-(-)-Gossypol acetic acid; NIOHNDKHQHVLKA-UHFFFAOYSA-N; (S)-Gossypol (acetic acid); R-(-)-gossypol acetic acid; Gossypol acetic acid, (R)-; (+/-)-Gossypol acetic acid; Gossypol acetic acid [MI]; Gossypol acetic acid, R-; (R)-Gossypol acetic acid; (-)-Gossypol acetic acid; (S)-Gossypol acetic acid; Gossypol (acetic acid); Gossypol acetate, (R)-; gossypol-Acetic acid; Gossypol acetic acid; Aceticacidgossypol; Gossypol xAcetate; Gossypol acetate; GossypolAcOHSalt; Acetate gossypol; Acetate-gossypol; Gossypol-acetic; GOSSYPOLACETATE; gosspyl acetate; UNII-U9GNI6VT5N; U9GNI6VT5N; (±)-Gossypol-acetic acid; BL-193 (acetic acid)



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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

  • Hao Liu, Ruirui Zhang, Dan Zhang, Chun Zhang, Zhuo Zhang, Xiujuan Fu, Yu Luo, Siwei Chen, Ailing Wu, Weiling Zeng, Kunyan Qu, Hao Zhang, Sijiao Wang, Houyin Shi. Cyclic RGD-Decorated Liposomal Gossypol AT-101 Targeting for Enhanced Antitumor Effect. International journal of nanomedicine. 2022; 17(?):227-244. doi: 10.2147/ijn.s341824. [PMID: 35068931]
  • Jian-Hong Lin, Kun-Ta Yang, Pei-Ching Ting, Yu-Po Luo, Ding-Jyun Lin, Yi-Shun Wang, Jui-Chih Chang. Gossypol Acetic Acid Attenuates Cardiac Ischemia/Reperfusion Injury in Rats via an Antiferroptotic Mechanism. Biomolecules. 2021 11; 11(11):. doi: 10.3390/biom11111667. [PMID: 34827665]
  • Laura Masuelli, Monica Benvenuto, Valerio Izzi, Erika Zago, Rosanna Mattera, Bruna Cerbelli, Vito Potenza, Sara Fazi, Sara Ciuffa, Ilaria Tresoldi, Enrico Lucarelli, Andrea Modesti, Roberto Bei. In vivo and in vitro inhibition of osteosarcoma growth by the pan Bcl-2 inhibitor AT-101. Investigational new drugs. 2020 06; 38(3):675-689. doi: 10.1007/s10637-019-00827-y. [PMID: 31264066]
  • Dorota K Flak, Vivian Adamski, Grzegorz Nowaczyk, Kosma Szutkowski, Michael Synowitz, Stefan Jurga, Janka Held-Feindt. AT101-Loaded Cubosomes as an Alternative for Improved Glioblastoma Therapy. International journal of nanomedicine. 2020; 15(?):7415-7431. doi: 10.2147/ijn.s265061. [PMID: 33116479]
  • Vivian Adamski, Christina Schmitt, Florian Ceynowa, Rainer Adelung, Ralph Lucius, Michael Synowitz, Kirsten Hattermann, Janka Held-Feindt. Effects of sequentially applied single and combined temozolomide, hydroxychloroquine and AT101 treatment in a long-term stimulation glioblastoma in vitro model. Journal of cancer research and clinical oncology. 2018 Aug; 144(8):1475-1485. doi: 10.1007/s00432-018-2680-y. [PMID: 29858681]
  • Nina Meyer, Svenja Zielke, Jonas B Michaelis, Benedikt Linder, Verena Warnsmann, Stefanie Rakel, Heinz D Osiewacz, Simone Fulda, Michel Mittelbronn, Christian Münch, Christian Behrends, Donat Kögel. AT 101 induces early mitochondrial dysfunction and HMOX1 (heme oxygenase 1) to trigger mitophagic cell death in glioma cells. Autophagy. 2018; 14(10):1693-1709. doi: 10.1080/15548627.2018.1476812. [PMID: 29938581]
  • Shuraila F Zerp, T Rianne Stoter, Frank J P Hoebers, Michiel W M van den Brekel, Ria Dubbelman, Gitta K Kuipers, M Vincent M Lafleur, Ben J Slotman, Marcel Verheij. Targeting anti-apoptotic Bcl-2 by AT-101 to increase radiation efficacy: data from in vitro and clinical pharmacokinetic studies in head and neck cancer. Radiation oncology (London, England). 2015 Jul; 10(?):158. doi: 10.1186/s13014-015-0474-9. [PMID: 26223311]
  • Aneel Paulus, Kasyapa Chitta, Sharoon Akhtar, David Personett, Kena C Miller, Kevin J Thompson, Jennifer Carr, Shaji Kumar, Vivek Roy, Stephen M Ansell, Joseph R Mikhael, Angela Dispenzieri, Craig B Reeder, Candido E Rivera, James Foran, Asher Chanan-Khan. AT-101 downregulates BCL2 and MCL1 and potentiates the cytotoxic effects of lenalidomide and dexamethasone in preclinical models of multiple myeloma and Waldenström macroglobulinaemia. British journal of haematology. 2014 Feb; 164(3):352-365. doi: 10.1111/bjh.12633. [PMID: 24236538]
  • Hongxia Lin, Murugesan K Gounder, Joseph R Bertino, Ah-Ng Tony Kong, Robert S DiPaola, Mark N Stein. A validated HPLC assay for the determination of R-(-)-gossypol in human plasma and its application in clinical pharmacokinetic studies. Journal of pharmaceutical and biomedical analysis. 2012 Jul; 66(?):371-5. doi: 10.1016/j.jpba.2012.03.029. [PMID: 22483642]
  • Selim Uzunoglu, Burcak Karaca, Harika Atmaca, Asli Kisim, Canfeza Sezgin, Bulent Karabulut, Ruchan Uslu. Comparison of XTT and Alamar blue assays in the assessment of the viability of various human cancer cell lines by AT-101 (-/- gossypol). Toxicology mechanisms and methods. 2010 Oct; 20(8):482-6. doi: 10.3109/15376516.2010.508080. [PMID: 20843265]
  • A S El-Sharaky, M M Wahby, M M Bader El-Dein, R A Fawzy, I N El-Shahawy. Mutual anti-oxidative effect of gossypol acetic acid and gossypol-iron complex on hepatic lipid peroxidation in male rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Nov; 47(11):2735-41. doi: 10.1016/j.fct.2009.08.001. [PMID: 19665044]
  • Zhan-Jun Yang, Wei-San Ye, Guang-Hui Cui, Yan Guo, She-Pu Xue. Combined administration of low-dose gossypol acetic acid with desogestrel/mini-dose ethinylestradiol/testosterone undecanoate as an oral contraceptive for men. Contraception. 2004 Sep; 70(3):203-11. doi: 10.1016/j.contraception.2004.02.019. [PMID: 15325889]
  • R W Hutchinson, R Barhoumi, J M Miles, R C Burghardt. Attenuation of gossypol cytotoxicity by cyclic AMP in a rat liver cell line. Toxicology and applied pharmacology. 1998 Aug; 151(2):311-8. doi: 10.1006/taap.1998.8461. [PMID: 9707507]
  • M S Wang, B J Lorenzo, M M Reidenberg. NAD- and NADP-dependent 11 beta-hydroxysteroid dehydrogenase isoforms in guinea pig kidney with gossypol inhibition. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1997 Nov; 18(6):481-5. doi: NULL. [PMID: 10322899]
  • B Yang, L Cao, Y Xu, Z X Sun, Z P Gu. [The effects of gossypol on rat luteal cells, human decidual cells and cytotrophoblasts]. Yao xue xue bao = Acta pharmaceutica Sinica. 1997 Aug; 32(8):573-7. doi: NULL. [PMID: 11596304]
  • Y W Zhang, M L Han, Y F Wang. [Estrogen and progesterone cytosol receptor concentrations in patients with endometriosis and their changes after gossypol therapy]. Zhonghua fu chan ke za zhi. 1994 Apr; 29(4):220-3, 253. doi: NULL. [PMID: 8082445]
  • G W Sang, B Lorenzo, M M Reidenberg. Inhibitory effects of gossypol on corticosteroid 11-beta-hydroxysteroid dehydrogenase from guinea pig kidney: a possible mechanism for causing hypokalemia. The Journal of steroid biochemistry and molecular biology. 1991 Aug; 39(2):169-76. doi: 10.1016/0960-0760(91)90058-d. [PMID: 1888675]
  • H Levinsky, R Singer, M Sagiv, N Lehrer, D Allalouf. Inhibition of sialyl transferase activity by gossypol acetic acid in human seminal plasma. Andrologia. 1991 Mar; 23(2):159-61. doi: 10.1111/j.1439-0272.1991.tb02522.x. [PMID: 1952122]
  • S Chadha, S N Sanyal, U Kanwar. Alterations and reversibility of the effects of gossypol acetic acid on the intestinal uptake of end product nutrients in normal and protein calorie-malnourished male rats. Annals of nutrition & metabolism. 1991; 35(1):53-60. doi: 10.1159/000177621. [PMID: 1905512]
  • Z P Gu, Y X Wang, G W Sang, W C Wang, Z X Chen, X J Zhao, Q X Shao, Y Jiang. Relationship between hormone profiles and the restoration of spermatogenesis in men treated with gossypol. International journal of andrology. 1990 Aug; 13(4):253-7. doi: 10.1111/j.1365-2605.1990.tb01029.x. [PMID: 2117586]
  • H F Huang, M Wang. [Effects of gossypol acetate, progesterone, danazol and GnRH-A (gonadotropin release hormone-A) on the DNA-synthesis of human endometrial cell in vitro]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1990 Aug; 10(8):476-8, 453. doi: ". [PMID: 2208435]
  • L F Xu, M Wang, C L Zhao. [Clinical effects and experimental study on gossypol in endometriosis]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1989 Aug; 9(8):462-4, 451. doi: . [PMID: 2598346]
  • Y Rikihisa, Y C Lin. Effect of gossypol on the thyroid in young rats. Journal of comparative pathology. 1989 May; 100(4):411-7. doi: 10.1016/0021-9975(89)90006-6. [PMID: 2760274]
  • P K Bajpai, H A Benghuzzi. Ceramic systems for long-term delivery of chemicals and biologicals. Journal of biomedical materials research. 1988 Dec; 22(12):1245-66. doi: 10.1002/jbm.820221212. [PMID: 3235459]
  • V Kainz, J Frick, P Kainz, N R Kalla, E Rovan, H Adam. The effect of gossypol acetic acid on the different stages of the spermatogenic cycle in the rat. International journal of andrology. 1988 Dec; 11(6):533-46. doi: 10.1111/j.1365-2605.1988.tb01026.x. [PMID: 3215704]
  • J M Wang, J P Qiu, X L Wu, Z R Zhang, Y Shao, R Q Cao. The correlation between the gossypol contents in blood plasma, rete testis fluid, and cauda epididymal fluid following chronic treatment with gossypol in rats. Journal of andrology. 1988 Nov; 9(6):397-402. doi: 10.1002/j.1939-4640.1988.tb01072.x. [PMID: 3215825]
  • R G Best, W H McKenzie. Variable sister-chromatid exchange response in human lymphocytes exposed in vitro to gossypol acetic acid. Mutation research. 1988 Oct; 206(2):227-33. doi: 10.1016/0165-1218(88)90165-6. [PMID: 3173390]
  • A de Peyster, H H Srebnik. Reproductive endocrine function in gossypol-treated male rats. International journal of fertility. 1988 Sep; 33(5):362-71. doi: NULL. [PMID: 2904425]
  • J M Reynolds, J N Tone. Subchronic oral administration of gossypol-acetic acid (GAA) alters the distribution and utilization of radioiron in male rats. Drug and chemical toxicology. 1988 Jun; 11(2):135-50. doi: 10.3109/01480548808998218. [PMID: 3402348]
  • R Heywood. The toxicology of gossypol acetic acid and (-)-gossypol. Contraception. 1988 Feb; 37(2):185-90. doi: 10.1016/0010-7824(88)90129-1. [PMID: 3370991]
  • Y F Fu, Z M Lu, W Wang. Gossypol inhibition of kidney (Na+ + K+)-ATPase. Chinese medical journal. 1987 Nov; 100(11):921-4. doi: NULL. [PMID: 2835209]
  • Y Q Yang, X Y Wu. Antifertility mechanisms of gossypol acetic acid in female rats. Journal of reproduction and fertility. 1987 Jul; 80(2):425-9. doi: 10.1530/jrf.0.0800425. [PMID: 3656277]
  • Y Wang, H P Lei. Hepatotoxicity of gossypol in rats. Journal of ethnopharmacology. 1987 Jun; 20(1):53-64. doi: 10.1016/0378-8741(87)90119-x. [PMID: 3626595]
  • I D Morris, C Higgins, S A Matlin. Inhibition of testicular LDH-X from laboratory animals and man by gossypol and its isomers. Journal of reproduction and fertility. 1986 Jul; 77(2):607-12. doi: 10.1530/jrf.0.0770607. [PMID: 3735252]
  • J N Tone, D R Jensen. Radioiron utilization and gossypol acetic acid in male rats. Drug and chemical toxicology. 1985; 8(1-2):69-82. doi: 10.3109/01480548509011635. [PMID: 4017900]
  • H Breitbart, S Rubinstein, L Nass-Arden. Effect of gossypol-acetic acid on calcium transport and ATPase activity in plasma membranes from ram and bull spermatozoa. International journal of andrology. 1984 Oct; 7(5):439-47. doi: 10.1111/j.1365-2605.1984.tb00801.x. [PMID: 6151940]
  • N Sattayasai, J Sattayasai, V Hahnvajanawong. High-performance liquid chromatographic determination of gossypol in plasma. Journal of chromatography. 1984 Apr; 307(1):235-9. doi: 10.1016/s0378-4347(00)84095-5. [PMID: 6725489]
  • R Eliasson, N Virji. Effects of gossypol acetic acid on the activity of LDH-C4 from human and rabbit spermatozoa. International journal of andrology. 1983 Feb; 6(1):109-12. doi: 10.1111/j.1365-2605.1983.tb00328.x. [PMID: 6840877]
  • N R Kalla, T W Foo, A R Sheth. Studies on the male antifertility agent--gossypol acetic acid. V. Effect of gossypol acetic acid on the fertility of male rats. Andrologia. 1982 Nov; 14(6):492-500. doi: 10.1111/j.1439-0272.1982.tb02299.x. [PMID: 7165122]
  • F Tang, A Y Tsang, C P Lee, P Y Wong. Inhibition of catechol-O-methyltransferase by gossypol: the effect of plasma proteins. Contraception. 1982 Nov; 26(5):515-9. doi: 10.1016/0010-7824(82)90150-0. [PMID: 7160182]
  • L F Zhou, H P Lei, Y Gao, Y Liu, N Y Wang, Y Guo. [Further observations on the effect of prolonged administration of gossypol acetic acid to rats]. Yao xue xue bao = Acta pharmaceutica Sinica. 1982 Apr; 17(4):245-52. doi: NULL. [PMID: 7136708]
  • N R Kalla, M Vasudev, G Arora. Studies on the male antifertility agent--gossypol acetic acid. III. Effect of gossypol acetic acid on rat testis. Andrologia. 1981 May; 13(3):242-9. doi: 10.1111/j.1439-0272.1981.tb00041.x. [PMID: 6455943]
  • N Loreau, C Lepreux, R Ardaillou. Calcitonin-sensitive adenylate cyclase in rat renal tubular membranes. The Biochemical journal. 1975 Sep; 150(3):305-14. doi: 10.1042/bj1500305. [PMID: 2153]