Bevirimat (BioDeep_00000230459)

   

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(4-hydroxy-3,3-dimethyl-4-oxo-butanoyl)oxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

化学式: C36H56O6 (584.4076676)
中文名称: 贝韦立马
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 77.78%

Reviewed

Last reviewed on 2024-08-19.

Cite this Page

Bevirimat. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/bevirimat (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000230459). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
InChI: InChI=1S/C36H56O6/c1-21(2)22-12-17-36(30(40)41)19-18-34(8)23(28(22)36)10-11-25-33(7)15-14-26(42-27(37)20-31(3,4)29(38)39)32(5,6)24(33)13-16-35(25,34)9/h22-26,28H,1,10-20H2,2-9H3,(H,38,39)(H,40,41)/t22-,23+,24-,25+,26-,28+,33-,34+,35+,36-/m0/s1

描述信息

Bevirimat is a pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems. It has a role as a metabolite and a HIV-1 maturation inhibitor. It is a pentacyclic triterpenoid, a dicarboxylic acid monoester and a monocarboxylic acid. It is functionally related to a betulinic acid.
Bevirimat, also known as PA-457 or YK-FH312, is investigated in clinical trials for treating HIV infection. Bevirimat is a solid. This compound belongs to the androgens and derivatives, which are hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Bevirimat targets the protein gag-pol polyprotein. Bevirimat is derived from a betulinic acid-like compound, first isolated from Syzygium claviflorum, a Chinese herb. It is not currently FDA-approved, but is undergoing clinical trials conducted by the pharmaceutical company Panacos.
Bevirimat is a drug derived from a betulinic acid-like compound, first isolated from the Chinese herb Syzygium claviflorum, with activity against human immunodeficiency virus (HIV). Bevirimat acts by binding to the Gag capsid precursor protein and blocking its conversion to mature capsid protein by protease cleavage. It potently inhibits replication in both wild-type and drug-resistant (reverse transciptase or protease) HIV-1 isolates.
A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.
C254 - Anti-Infective Agent > C281 - Antiviral Agent > C1660 - Anti-HIV Agent
Bevirimat (PA-457; MPC-4326; YK FH312) is an anti-HIV agent derived from a betulinic acid-like compound; is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition.
Bevirimat (PA-457; MPC-4326; YK FH312) is an anti-HIV agent derived from a betulinic acid-like compound; is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition.

同义名列表

35 个代谢物同义名

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(4-hydroxy-3,3-dimethyl-4-oxo-butanoyl)oxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-((3-carboxy-3-methylbutanoyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-((3-carboxy-3-methylbutanoyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-9-(3-carboxy-3-methylbutanoyloxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid; 2,2-Dimethyl-succinic acid, 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-carboxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl) ester; 2,2-Dimethyl-succinic acid 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-carboxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl) ester; lup-20(29)-en-28-oic acid, 3-(3-carboxy-3-methyl-1-oxobutoxy)-, (3beta)-, compd. with 1-deoxy-1-(methylamino)-D-glucitol (1:2); 3alpha-[(3-carboxy-3-methylbutanoyl)oxy]-8alpha,9beta,10alpha,13alpha,17alpha,19beta-lup-20(29)-en-28-oic acid; bis(1-deoxy-1-(methylamino)-D-glucitol) 3beta-(3-carboxylato-3-methylbutanoyloxy)lup-20(29)-en-28-oate; Lup-20(29)-en-28-oic acid, 3-(3-carboxy-3-methyl-1-oxobutoxy)-, (3beta)-; (3beta)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid; 3beta-(3-Carboxy-3-methylbutanoyloxy)lup-20(29)-en-28-oic acid; 3-O-(3,3-dimethyl-succinyl)-betulinic acid; 3-O-(3,3-dimethylsuccinyl)-betulinic acid; 3-O-(3,3-Dimethylsuccinyl)-betulinic acid; 3-O-(3,3-dimethylsuccinyl) betulinic acid; 3-O-(3,3-dimethylsuccinyl)betulinic acid; O-(3,3-Dimethylsuccinyl)betulinic acid; YJEJKUQEXFSVCJ-WRFMNRASSA-N; bevirimat dimeglumine salt; Bevirimat, >=98\\% (HPLC); bevirimat-dimeglumine; bevirimat dimeglumine; Bevirimat [INN]; BEVIRIMAT [MI]; bevirimatum; Bevirimat; dsb-2nmg; BVM; 2I4; DSB; PA-457; MPC-4326; YK FH312



数据库引用编号

10 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)

2 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

  • Martina Wimmerová, Uladzimir Bildziukevich, Zdeněk Wimmer. Selected Plant Triterpenoids and Their Derivatives as Antiviral Agents. Molecules (Basel, Switzerland). 2023 Nov; 28(23):. doi: 10.3390/molecules28237718. [PMID: 38067449]
  • Zixuan Zhao, Yinghong Ma, Xiangyuan Li, Susan L Morris-Natschke, Zhaocui Sun, Zhonghao Sun, Guoxu Ma, Zhengqi Dong, Xiaohong Zhao, Meihua Yang, Xudong Xu, Kuohsiung Lee, Haifeng Wu, Chinho Chen. Anti-HIV Potential of Beesioside I Derivatives as Maturation Inhibitors: Synthesis, 3D-QSAR, Molecular Docking and Molecular Dynamics Simulations. International journal of molecular sciences. 2023 Jan; 24(2):. doi: 10.3390/ijms24021430. [PMID: 36674943]
  • Li Zhao, Hong-Hong He, Ting Ou-Yang, Di-Fa Liu, Chun-Hong Jiang, He-Ping Yang, Pei Wang, Ning Xie, Shou-Sheng Yan. Pre-clinical pharmacological profile of QF-036, a potent HIV-1 maturation inhibitor. Basic & clinical pharmacology & toxicology. 2021 Feb; 128(2):275-285. doi: 10.1111/bcpt.13504. [PMID: 33012100]
  • Sebanti Gupta, John M Louis, Robert Tycko. Effects of an HIV-1 maturation inhibitor on the structure and dynamics of CA-SP1 junction helices in virus-like particles. Proceedings of the National Academy of Sciences of the United States of America. 2020 05; 117(19):10286-10293. doi: 10.1073/pnas.1917755117. [PMID: 32341150]
  • Haifeng Wu, Guoxu Ma, Qinwen Yang, Yindi Zhu, Li Huang, Yu Tian, Xiaoming Yang, Menghan Zhang, Chin-Ho Chen, Susan L Morris-Natschke, Meihua Yang, Xudong Xu, Kuo-Hsiung Lee. Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity. European journal of medicinal chemistry. 2019 Mar; 166(?):159-166. doi: 10.1016/j.ejmech.2019.01.020. [PMID: 30703659]
  • Yan Chen, Sing-Yuen Sit, Jie Chen, Jacob J Swidorski, Zheng Liu, Ny Sin, Brian L Venables, Dawn D Parker, Beata Nowicka-Sans, Zeyu Lin, Zhufang Li, Brian J Terry, Tricia Protack, Sandhya Rahematpura, Umesh Hanumegowda, Susan Jenkins, Mark Krystal, Ira D Dicker, Nicholas A Meanwell, Alicia Regueiro-Ren. The design, synthesis and structure-activity relationships associated with C28 amine-based betulinic acid derivatives as inhibitors of HIV-1 maturation. Bioorganic & medicinal chemistry letters. 2018 05; 28(9):1550-1557. doi: 10.1016/j.bmcl.2018.03.067. [PMID: 29631960]
  • Beata Nowicka-Sans, Tricia Protack, Zeyu Lin, Zhufang Li, Sharon Zhang, Yongnian Sun, Himadri Samanta, Brian Terry, Zheng Liu, Yan Chen, Ny Sin, Sing-Yuen Sit, Jacob J Swidorski, Jie Chen, Brian L Venables, Matthew Healy, Nicholas A Meanwell, Mark Cockett, Umesh Hanumegowda, Alicia Regueiro-Ren, Mark Krystal, Ira B Dicker. Identification and Characterization of BMS-955176, a Second-Generation HIV-1 Maturation Inhibitor with Improved Potency, Antiviral Spectrum, and Gag Polymorphic Coverage. Antimicrobial agents and chemotherapy. 2016 07; 60(7):3956-69. doi: 10.1128/aac.02560-15. [PMID: 27090171]
  • Zheng Liu, Jacob J Swidorski, Beata Nowicka-Sans, Brian Terry, Tricia Protack, Zeyu Lin, Himadri Samanta, Sharon Zhang, Zhufang Li, Dawn D Parker, Sandhya Rahematpura, Susan Jenkins, Brett R Beno, Mark Krystal, Nicholas A Meanwell, Ira B Dicker, Alicia Regueiro-Ren. C-3 benzoic acid derivatives of C-3 deoxybetulinic acid and deoxybetulin as HIV-1 maturation inhibitors. Bioorganic & medicinal chemistry. 2016 Apr; 24(8):1757-70. doi: 10.1016/j.bmc.2016.03.001. [PMID: 26968652]
  • Jacob J Swidorski, Zheng Liu, Sing-Yuen Sit, Jie Chen, Yan Chen, Ny Sin, Brian L Venables, Dawn D Parker, Beata Nowicka-Sans, Brian J Terry, Tricia Protack, Sandhya Rahematpura, Umesh Hanumegowda, Susan Jenkins, Mark Krystal, Ira B Dicker, Nicholas A Meanwell, Alicia Regueiro-Ren. Inhibitors of HIV-1 maturation: Development of structure-activity relationship for C-28 amides based on C-3 benzoic acid-modified triterpenoids. Bioorganic & medicinal chemistry letters. 2016 Apr; 26(8):1925-30. doi: 10.1016/j.bmcl.2016.03.019. [PMID: 26988305]
  • Oliver Callies, Luis M Bedoya, Manuela Beltrán, Alejandro Muñoz, Patricia Obregón Calderón, Alex A Osorio, Ignacio A Jiménez, José Alcamí, Isabel L Bazzocchi. Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina. Journal of natural products. 2015 May; 78(5):1045-55. doi: 10.1021/np501025r. [PMID: 25927586]
  • Nicolas A Margot, Craig S Gibbs, Michael D Miller. Phenotypic susceptibility to bevirimat in isolates from HIV-1-infected patients without prior exposure to bevirimat. Antimicrobial agents and chemotherapy. 2010 Jun; 54(6):2345-53. doi: 10.1128/aac.01784-09. [PMID: 20308382]
  • Kuo-Hsiung Lee. Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. Journal of natural products. 2010 Mar; 73(3):500-16. doi: 10.1021/np900821e. [PMID: 20187635]
  • Yan Jiang, Xin-yong Liu. [The role of structural protein Gag and related gene (protein) in late stages of the HIV-1 replication cycle and the inhibitors]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Feb; 45(2):205-14. doi: ". [PMID: 21351430]
  • Sanjay Bhattacharya, Husam Osman. Novel targets for anti-retroviral therapy. The Journal of infection. 2009 Dec; 59(6):377-86. doi: 10.1016/j.jinf.2009.09.014. [PMID: 19815027]
  • Sandrina Dafonseca, Pascale Coric, Bernard Gay, Saw See Hong, Serge Bouaziz, Pierre Boulanger. The inhibition of assembly of HIV-1 virus-like particles by 3-O-(3',3'-dimethylsuccinyl) betulinic acid (DSB) is counteracted by Vif and requires its Zinc-binding domain. Virology journal. 2008 Dec; 5(?):162. doi: 10.1186/1743-422x-5-162. [PMID: 19105849]
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  • David E Martin, Robert Blum, John Wilton, Judy Doto, Hal Galbraith, Gina L Burgess, Philip C Smith, Charles Ballow. Safety and pharmacokinetics of Bevirimat (PA-457), a novel inhibitor of human immunodeficiency virus maturation, in healthy volunteers. Antimicrobial agents and chemotherapy. 2007 Sep; 51(9):3063-6. doi: 10.1128/aac.01391-06. [PMID: 17576843]
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  • David E Martin, Robert Blum, Judy Doto, Hal Galbraith, Charles Ballow. Multiple-dose pharmacokinetics and safety of bevirimat, a novel inhibitor of HIV maturation, in healthy volunteers. Clinical pharmacokinetics. 2007; 46(7):589-98. doi: 10.2165/00003088-200746070-00004. [PMID: 17596104]
  • Zhiming Wen, Stephan T Stern, David E Martin, Kuo-Hsiung Lee, Philip C Smith. Structural characterization of anti-HIV drug candidate PA-457 [3-O-(3',3'-dimethylsuccinyl)-betulinic acid] and its acyl glucuronides in rat bile and evaluation of in vitro stability in human and animal liver microsomes and plasma. Drug metabolism and disposition: the biological fate of chemicals. 2006 Sep; 34(9):1436-42. doi: 10.1124/dmd.106.009233. [PMID: 16751262]
  • Jing Zhou, Chin Ho Chen, Christopher Aiken. The sequence of the CA-SP1 junction accounts for the differential sensitivity of HIV-1 and SIV to the small molecule maturation inhibitor 3-O-{3',3'-dimethylsuccinyl}-betulinic acid. Retrovirology. 2004 Jun; 1(?):15. doi: 10.1186/1742-4690-1-15. [PMID: 15225375]
  • Kuo-Hsiung Lee. Current developments in the discovery and design of new drug candidates from plant natural product leads. Journal of natural products. 2004 Feb; 67(2):273-83. doi: 10.1021/np030373o. [PMID: 14987069]