Betulonic acid (BioDeep_00000236404)

PANOMIX_OTCML-2023

代谢物信息卡片

(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid

化学式: C30H46O3 (454.34467659999996)
中文名称: 白桦脂酮酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)C(=O)O
InChI: InChI=1S/C30H46O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-22,24H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,24+,27-,28+,29+,30-/m0/s1

描述信息

Betulonic acid (Betunolic acid), a naturally occurring triterpene, is found in many plants. Betulonic acid has anti-tumor, anti-inflammatory, antiparasitic and anti-viral (HSV-1) activities[2][1][3][4].
Betulonic acid (Betunolic acid), a naturally occurring triterpene, is found in many plants. Betulonic acid has anti-tumor, anti-inflammatory, antiparasitic and anti-viral (HSV-1) activities[2][1][3][4].

同义名列表

11 个代谢物同义名

(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid; Lup-20(29)-en-28-oic acid, 3-oxo-; 3-Oxolup-20(29)-en-28-oic acid; 3-Deoxy-3-oxo-betulinic acid; Betulonic acid; AIDS-051817; AIDS051817; 4481-62-3; (+)-Betulonic Acid; Betunolic acid; Liquidambaric acid

数据库引用编号

7 个数据库交叉引用编号

ChEBI: CHEBI:149955
PubChem: 122844
Metlin: METLIN263484
ChEMBL: CHEMBL431525
KNApSAcK: C00035253
CAS: 4481-62-3
medchemexpress: HY-N1451

分类词条

萜类

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)

47 个相关的物种来源信息

216992 - Betula ermanii: 10.1002/CBDV.200800266
78630 - Betula platyphylla: 10.1021/NP060631S
216986 - Betula schmidtii: 10.1248/CPB.46.1051
1764335 - Boronia gracilipes: 10.1016/0031-9422(94)00567-D
1764338 - Boronia inornata: 10.1016/0031-9422(94)00567-D
210348 - Brucea javanica: 10.1002/JCCS.200500117
61143 - Ceriops tagal: 10.1021/NP0502793
155629 - Chisocheton macrophyllus: 10.1248/CPB.41.617
16906 - Cornus Officinalis Sieb. Et Zucc.: -
34329 - Corymbia citriodora: 10.1002/JCCS.200000074
195737 - Duboisia myoporoides: 10.1016/S0031-9422(00)80500-2
183855 - Eucalyptus tereticornis: 10.1016/0031-9422(93)85412-K
66385 - Ficus microcarpa: 10.1016/J.PHYTOCHEM.2004.12.026
228586 - Humulus Scandens (Lour.) Merr.: -
43503 - Ixora coccinea: 10.1016/J.BMCL.2010.10.058
126435 - Lantana camara: 10.14233/AJCHEM.2014.16935
63359 - Liquidambar formosana: 10.1055/S-2006-962410
4400 - Liquidambar styraciflua: 10.1002/(SICI)1096-9063(199902)55:2<205::AID-PS870>3.0.CO;2-2
490002 - Maytenus boaria:
164936 - Melaleuca leucadendra: 10.1021/NP9606052
28950 - Nothofagus pumilio: 10.1016/J.PHYTOCHEM.2004.04.002
289732 - Orthopterygium: 10.1016/S0031-9422(00)80284-8
1284867 - Ozothamnus stirlingii: 10.1016/S0031-9422(00)84791-3
33090 - Plants: -
56065 - Pongamia pinnata: 10.1016/J.BMCL.2014.11.015
479656 - Rhododendron barbatum: 10.1021/NP50050A045
289753 - Rhus chinensis: 10.1055/S-2007-967113
381101 - Senegalia mellifera: 10.1016/J.PHYTOCHEM.2004.03.002
41788 - Stauntonia hexaphylla: 10.1016/S0031-9422(97)00588-8
1745164 - Symphyopappus compressus: 10.1016/S0031-9422(00)98550-9
2029442 - Vatica harmandiana: 10.1021/NP020379Y
159976 - Viscum coloratum:
326968 - Ziziphus jujuba: 10.1248/CPB.26.3075
326968 - Ziziphus jujuba Mill.: -
157914 - Ziziphus mauritiana: 10.1055/S-2003-45155
124778 - 八角茴香: -
33090 - 大枣: -
33090 - 大皂荚: -
33090 - 山茱萸: -
33090 - 白头翁: -
33090 - 皂角刺: -
33090 - 肿节风: -
33090 - 葎草: -
33090 - 路路通: -
33090 - 连翘: -
33090 - 金樱子: -
33090 - 鼠曲草: -

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

Olexander M Semenenko, Victoria V Lipson, Alina O Sadchenko, Olga V Vashchenko, Natalia A Kasian, Liliia V Sviechnikova, Longin M Lisetski, Mykola L Babak, Volodymyr M Vakula, Oleksandr V Borysov, Yuliia V Holota, Sergey O Zozulya, Petro O Borysko, Olexander V Mazepa. Synthesis of methotrexate-betulonic acid hybrids and evaluation of their effect on artificial and Caco-2 cell membranes. Steroids. 2024 Jan; 201(?):109332. doi: 10.1016/j.steroids.2023.109332. [PMID: 37939980]
Liang Shao, Yan Yan, Nansu Wang, Qiongfang Tan, Yuying Huang, Lei Lei, Dongmei Yang, Ling Liu. Betulonic acid regulates oviduct epithelial cell inflammation through the TLR4, MAPK, and JAK/STAT signalling pathways. Reproduction, fertility, and development. 2023 May; 35(8):480-491. doi: 10.1071/rd21380. [PMID: 37142241]
Zewen Chu, Yuanyuan Luo, Tengyang Ni, Miao Zhu, Xinyi Feng, Yanqing Liu, Haibo Wang. Betulonic Acid, as One of the Active Components of the Celastrus orbiculatus Extract, Inhibits the Invasion and Metastasis of Gastric Cancer Cells by Mediating Cytoskeleton Rearrangement In Vitro. Molecules (Basel, Switzerland). 2022 Feb; 27(3):. doi: 10.3390/molecules27031025. [PMID: 35164287]
Kai-Nan Song, You-Jia Lu, Cheng-Jiao Chu, Yan-Ni Wu, Hui-Lian Huang, Bo-Yi Fan, Guang-Tong Chen. Biotransformation of Betulonic Acid by the Fungus Rhizopus arrhizus CGMCC 3.868 and Antineuroinflammatory Activity of the Biotransformation Products. Journal of natural products. 2021 10; 84(10):2664-2674. doi: 10.1021/acs.jnatprod.1c00480. [PMID: 34546050]
Mikhail V Dubinin, Alena A Semenova, Anna I Ilzorkina, Irina B Mikheeva, Valery A Yashin, Nikita V Penkov, Valentina A Vydrina, Gumer Yu Ishmuratov, Vyacheslav A Sharapov, Ekaterina I Khoroshavina, Sergey V Gudkov, Konstantin N Belosludtsev. Effect of betulin and betulonic acid on isolated rat liver mitochondria and liposomes. Biochimica et biophysica acta. Biomembranes. 2020 10; 1862(10):183383. doi: 10.1016/j.bbamem.2020.183383. [PMID: 32522531]
Ziyad Tariq Muhseen, Guanglin Li. Promising Terpenes as Natural Antagonists of Cancer: An In-Silico Approach. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010155. [PMID: 31906032]
Yao Li, Sheng Guo, Quanjin Ren, Dandan Wei, Ming Zhao, Shulan Su, Zhishu Tang, Jin-Ao Duan. Pharmacokinetic Comparisons of Multiple Triterpenic Acids from Jujubae Fructus Extract Following Oral Delivery in Normal and Acute Liver Injury Rats. International journal of molecular sciences. 2018 07; 19(7):. doi: 10.3390/ijms19072047. [PMID: 30011885]
Suvi T Häkkinen, Heli Nygren, Natalia Maiorova, Raisa Haavikko, Sami Alakurtti, Jari Yli-Kauhaluoma, Heiko Rischer, Kirsi-Marja Oksman-Caldentey. Biotransformation of Cyclodextrine-Complexed Semisynthetic Betulin Derivatives by Plant Cells. Planta medica. 2018 Jul; 84(9-10):743-748. doi: 10.1055/a-0585-6081. [PMID: 29518814]
Lía S Valencia-Chan, Isabel García-Cámara, Luis W Torres-Tapia, Rosa E Moo-Puc, Sergio R Peraza-Sánchez. Lupane-Type Triterpenes of Phoradendron vernicosum. Journal of natural products. 2017 11; 80(11):3038-3042. doi: 10.1021/acs.jnatprod.7b00177. [PMID: 29120172]
Kok Hoong Leong, Mohamad Azrul Mahdzir, Mohd Fadzli Md Din, Khalijah Awang, Yuka Tanaka, Kasem Kulkeaw, Tohru Ishitani, Daisuke Sugiyama. Induction of intrinsic apoptosis in leukaemia stem cells and in vivo zebrafish model by betulonic acid isolated from Walsura pinnata Hassk (Meliaceae). Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Mar; 26(?):11-21. doi: 10.1016/j.phymed.2016.12.018. [PMID: 28257660]
Hongliang Wu, Guoliang Li, Shucheng Liu, Di Liu, Guang Chen, Na Hu, Yourui Suo, Jinmao You. Simultaneous determination of six triterpenic acids in some Chinese medicinal herbs using ultrasound-assisted dispersive liquid-liquid microextraction and high-performance liquid chromatography with fluorescence detection. Journal of pharmaceutical and biomedical analysis. 2015 Mar; 107(?):98-107. doi: 10.1016/j.jpba.2014.10.031. [PMID: 25569287]
Jiayuan Li, Zhe Jiang, Xuezheng Li, Yue Hou, Fen Liu, Ning Li, Xia Liu, Lihua Yang. Natural therapeutic agents for neurodegenerative diseases from a traditional herbal medicine Pongamia pinnata (L.) Pierre. Bioorganic & medicinal chemistry letters. 2015 Jan; 25(1):53-8. doi: 10.1016/j.bmcl.2014.11.015. [PMID: 25466192]
Sheng-Jie Yang, Ming-Chuan Liu, Qi Zhao, De-Yu Hu, Wei Xue, Song Yang. Synthesis and biological evaluation of betulonic acid derivatives as antitumor agents. European journal of medicinal chemistry. 2015; 96(?):58-65. doi: 10.1016/j.ejmech.2015.04.006. [PMID: 25874331]
Jifeng Gu, Guoqiang Ding, Nianzu Chen, Zhen Zhang. Development and validation of a sensitive LC-MS-MS assay for the quantification of betulonic acid in rat plasma. Journal of chromatographic science. 2014 Mar; 52(3):195-200. doi: 10.1093/chromsci/bmt010. [PMID: 23446289]
Sergey F Vasilevsky, Anastasiya I Govdi, Irina V Sorokina, Tatyana G Tolstikova, Dmitry S Baev, Genrikh A Tolstikov, Victor I Mamatuyk, Igor V Alabugin. Rapid access to new bioconjugates of betulonic acid via click chemistry. Bioorganic & medicinal chemistry letters. 2011 Jan; 21(1):62-5. doi: 10.1016/j.bmcl.2010.11.072. [PMID: 21159508]
Chia-Lin Lee, Yung-Chih Liao, Tsong-Long Hwang, Chin-Chung Wu, Fang-Rong Chang, Yang-Chang Wu. Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea. Bioorganic & medicinal chemistry letters. 2010 Dec; 20(24):7354-7. doi: 10.1016/j.bmcl.2010.10.058. [PMID: 21106454]
Fatma M Abdel Bar, Mohammad A Khanfar, Ahmed Y Elnagar, Hui Liu, Ahmed M Zaghloul, Farid A Badria, Paul W Sylvester, Kadria F Ahmad, Kevin P Raisch, Khalid A El Sayed. Rational design and semisynthesis of betulinic acid analogues as potent topoisomerase inhibitors. Journal of natural products. 2009 Sep; 72(9):1643-50. doi: 10.1021/np900312u. [PMID: 19691293]
Chih-Chun Wen, Yueh-Hsiung Kuo, Jia-Tsrong Jan, Po-Huang Liang, Sheng-Yang Wang, Hong-Gi Liu, Ching-Kuo Lee, Shang-Tzen Chang, Chih-Jung Kuo, Shoei-Sheng Lee, Chia-Chung Hou, Pei-Wen Hsiao, Shih-Chang Chien, Lie-Fen Shyur, Ning-Sun Yang. Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. Journal of medicinal chemistry. 2007 Aug; 50(17):4087-95. doi: 10.1021/jm070295s. [PMID: 17663539]
Qiong Gu, Rui-Rui Wang, Xue-Mei Zhang, Yun-Hua Wang, Yong-Tang Zheng, Jun Zhou, Ji-Jun Chen. A new benzofuranone and anti-HIV constituents from the stems of Rhus chinensis. Planta medica. 2007 Mar; 73(3):279-82. doi: 10.1055/s-2007-967113. [PMID: 17290322]
Denise Z L Bastos, Ida C Pimentel, Daniel A de Jesus, Brás H de Oliveira. Biotransformation of betulinic and betulonic acids by fungi. Phytochemistry. 2007 Mar; 68(6):834-9. doi: 10.1016/j.phytochem.2006.12.007. [PMID: 17258248]
Sang Zin Choi, Min Cheol Yang, Sang Un Choi, Kang Ro Lee. Cytotoxic terpenes and lignans from the roots of Ainsliaea acerifolia. Archives of pharmacal research. 2006 Mar; 29(3):203-8. doi: 10.1007/bf02969394. [PMID: 16596992]
Qi-Wei Zhang, Yong-Xin Zhang, Yu-Ru Sun, Dong Zhang. [Qualitative and quantitative methods of betulonic acid in fruits of Liquidambar formosana]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Aug; 30(15):1168-70. doi: ". [PMID: 16201692]
Shun-ichi Wada, Reiko Tanaka. Betulinic acid and its derivatives, potent DNA topoisomerase II inhibitors, from the bark of Bischofia javanica. Chemistry & biodiversity. 2005 May; 2(5):689-94. doi: 10.1002/cbdv.200590045. [PMID: 17192012]
N I Pavlova, O V Savinova, S N Nikolaeva, E I Boreko, O B Flekhter. Antiviral activity of betulin, betulinic and betulonic acids against some enveloped and non-enveloped viruses. Fitoterapia. 2003 Jul; 74(5):489-92. doi: 10.1016/s0367-326x(03)00123-0. [PMID: 12837369]
Hong-Jie Zhang, Ghee Teng Tan, Vu Dinh Hoang, Nguyen Van Hung, Nguyen Manh Cuong, D Doel Soejarto, John M Pezzuto, Harry H S Fong. Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea. Journal of natural products. 2003 Feb; 66(2):263-8. doi: 10.1021/np020379y. [PMID: 12608862]
Bin Chen, Mei Zhu, Wang-xing Xing, Gen-jing Yang, He-ming Mi, Yu-tian Wu. [Studies on chemical constituents in fruit of Eucalyptus globulus]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2002 Aug; 27(8):596-7. doi: ". [PMID: 12776496]
J Ito, F R Chang, H K Wang, Y K Park, M Ikegaki, N Kilgore, K H Lee. Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. Journal of natural products. 2001 Oct; 64(10):1278-81. doi: 10.1021/np010211x. [PMID: 11678650]
M Kurokawa, P Basnet, M Ohsugi, T Hozumi, S Kadota, T Namba, T Kawana, K Shiraki. Anti-herpes simplex virus activity of moronic acid purified from Rhus javanica in vitro and in vivo. The Journal of pharmacology and experimental therapeutics. 1999 Apr; 289(1):72-8. doi: ". [PMID: 10086989]