Isopimaric acid (BioDeep_00000000919)

 

Secondary id: BioDeep_00000411762, BioDeep_00000861078

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-, (1theta-(1alpha,4abeta,4balpha,7alpha,10aalpha))-

化学式: C20H30O2 (302.224568)
中文名称: 异海松酸, 异海松酸
谱图信息: 最多检出来源 Viridiplantae(plant) 7.35%

分子结构信息

SMILES: C1C[C@@]([C@H]2[C@](C1)([C@@H]1C(=CC2)C[C@](CC1)(C=C)C)C)(C)C(=O)O
InChI: InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1

描述信息

Isopimaric acid is a diterpenoid, a carbotricyclic compound and a monocarboxylic acid. It is a conjugate acid of an isopimarate. It derives from a hydride of an isopimara-7,15-diene.
Isopimaric acid is a natural product found in Pinus brutia var. eldarica, Halocarpus bidwillii, and other organisms with data available.
Isopimaric acid is isolated from Pinus palustris (pitch pine).
D049990 - Membrane Transport Modulators
D007476 - Ionophores
Isopimaric acid is a potent opener of large conductance calcium activated K+ (BK) channels.
Isopimaric acid is a potent opener of large conductance calcium activated K+ (BK) channels.

同义名列表

34 个代谢物同义名

1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-, (1theta-(1alpha,4abeta,4balpha,7alpha,10aalpha))-; 1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R,4aR,4bS,7S,10aR)-; (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid; (1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid; (1R,4AR,4BS,7S,10ar)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylate; 7,15-Isopimaradien-18-oic acid; Isopimaric acid A; 7,15-Isopimaric acid; Podocarp-7-en-15-oic acid, 13.beta.-methyl-13-vinyl-, (-)-; PODOCARP-7-EN-15-OIC ACID, 13.BETA.-METHYL-13-VINYL-; (-)-13beta-Methyl-13-vinylpodocarp-7-en-15-Oic acid; (-)-13Β-methyl-13-vinylpodocarp-7-en-15-Oic acid; 13beta-Methyl-13-vinylpodocarp-7-en-15-Oic acid; 13Β-methyl-13-vinylpodocarp-7-en-15-Oic acid; (5ξ,9ξ,13α)-Pimara-7,15-dien-18-oic acid; (13alpha)-pimara-7,15-dien-18-oic acid; Isopimaric Acid, >=98\\% (GC), powder; (13S)-pimara-7,15-dien-18-oic acid; 7,15-Isopimaradien-18-oic Acid; .DELTA.7,15-ISOPIMARIC ACID; delta7,15-Isopimaric acid; Neoisodextropimaric acid; 4-epi-isopimaric acid; isodextropimaric acid; Δ7,15-isopimaric acid; ISOPIMARIC ACID [MI]; (+)-Isopimaric Acid; 4-Epi-isopimarate; Isopimaric acid A; UNII-1E37K85HHK; Isopimaric acid; Micropinic acid; Miropinic Acid; ISOPIMARICACID; Isopimarate; 1E37K85HHK



数据库引用编号

22 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(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

86 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

  • Jiacheng Li, Xiaozhen Liu, Lin Chen, Xinping Zhu, Zhihong Yu, Liyao Dong, Xinyun Zhao, Hongling Zou, Qin Wei, Yongcai Feng, Yongqiang Zhu, Kequn Chai, Qun Li, Mingqian Li. Isopimaric acid, an ion channel regulator, regulates calcium and oxidative phosphorylation pathways to inhibit breast cancer proliferation and metastasis. Toxicology and applied pharmacology. 2023 Mar; 462(?):116415. doi: 10.1016/j.taap.2023.116415. [PMID: 36754215]
  • Doudou Huang, Jiaxi Cheng, Junqin Mao, Senlin Ma, Zenan Du, Wansheng Chen, Feng Zhang, Lianna Sun. The LC-MS/MS-Based Measurement of Isopimaric Acid in Rat Plasma and Application of Pharmacokinetics. BioMed research international. 2021; 2021(?):2310422. doi: 10.1155/2021/2310422. [PMID: 34692827]
  • S Salari, M Silverå Ejneby, J Brask, F Elinder. Isopimaric acid - a multi-targeting ion channel modulator reducing excitability and arrhythmicity in a spontaneously beating mouse atrial cell line. Acta physiologica (Oxford, England). 2018 01; 222(1):. doi: 10.1111/apha.12895. [PMID: 28514017]
  • Katrin Geisler, Niels Berg Jensen, Macaire M S Yuen, Lina Madilao, Jörg Bohlmann. Modularity of Conifer Diterpene Resin Acid Biosynthesis: P450 Enzymes of Different CYP720B Clades Use Alternative Substrates and Converge on the Same Products. Plant physiology. 2016 05; 171(1):152-64. doi: 10.1104/pp.16.00180. [PMID: 26936895]
  • Dawn E Hall, Philipp Zerbe, Sharon Jancsik, Alfonso Lara Quesada, Harpreet Dullat, Lina L Madilao, Macaire Yuen, Jörg Bohlmann. Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases. Plant physiology. 2013 Feb; 161(2):600-16. doi: 10.1104/pp.112.208546. [PMID: 23370714]
  • Axel Schmidt, Raimund Nagel, Trygve Krekling, Erik Christiansen, Jonathan Gershenzon, Paal Krokene. Induction of isoprenyl diphosphate synthases, plant hormones and defense signalling genes correlates with traumatic resin duct formation in Norway spruce (Picea abies). Plant molecular biology. 2011 Dec; 77(6):577-90. doi: 10.1007/s11103-011-9832-7. [PMID: 22002747]
  • Flavia Carmelina Massaro, Peter Richard Brooks, Helen Margaret Wallace, Fraser Donald Russell. Cerumen of Australian stingless bees (Tetragonula carbonaria): gas chromatography-mass spectrometry fingerprints and potential anti-inflammatory properties. Die Naturwissenschaften. 2011 Apr; 98(4):329-37. doi: 10.1007/s00114-011-0770-7. [PMID: 21347735]
  • Anne-Marie Nam, Mathieu Paoli, Vincent Castola, Joseph Casanova, Ange Bighelli. Identification and quantitative determination of lignans in Cedrus atlantica resins using 13C NMR spectroscopy. Natural product communications. 2011 Mar; 6(3):379-85. doi: . [PMID: 21485279]
  • Young Bae Ryu, Hyung Jae Jeong, Jang Hoon Kim, Young Min Kim, Ji-Young Park, Doman Kim, Thi Thanh Hanh Nguyen, Su-Jin Park, Jong Sun Chang, Ki Hun Park, Mun-Chual Rho, Woo Song Lee. Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition. Bioorganic & medicinal chemistry. 2010 Nov; 18(22):7940-7. doi: 10.1016/j.bmc.2010.09.035. [PMID: 20934345]
  • Eric Abbott, Dawn Hall, Björn Hamberger, Jörg Bohlmann. Laser microdissection of conifer stem tissues: isolation and analysis of high quality RNA, terpene synthase enzyme activity and terpenoid metabolites from resin ducts and cambial zone tissue of white spruce (Picea glauca). BMC plant biology. 2010 Jun; 10(?):106. doi: 10.1186/1471-2229-10-106. [PMID: 20540781]
  • Reiko Tanaka, Harukuni Tokuda, Yoichiro Ezaki. Cancer chemopreventive activity of "rosin" constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Nov; 15(11):985-92. doi: 10.1016/j.phymed.2008.02.020. [PMID: 18424098]
  • Wen-Hsin Li, Shang-Tzen Chang, Shan-Chwen Chang, Hui-Ting Chang. Isolation of antibacterial diterpenoids from Cryptomeria japonica bark. Natural product research. 2008; 22(12):1085-93. doi: 10.1080/14786410802267510. [PMID: 18780250]
  • Julieta Rubio, José S Calderón, Angélica Flores, Clementina Castroa, Carlos L Céspedes. Trypanocidal activity of oleoresin and terpenoids isolated from Pinus oocarpa. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2005 Sep; 60(9-10):711-6. doi: 10.1515/znc-2005-9-1009. [PMID: 16320613]
  • Eileen Smith, Elizabeth Williamson, Mire Zloh, Simon Gibbons. Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus. Phytotherapy research : PTR. 2005 Jun; 19(6):538-42. doi: 10.1002/ptr.1711. [PMID: 16114093]
  • Bao-hua Yang, Wei-dong Zhang, Zheng-bing Gu, Ting-zhao Li, Chuang Zhang, Yun Zhou. [Studies on chemical constituents in bark of Larix olgensis var. koreana]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Feb; 30(4):270-2. doi: . [PMID: 15724403]
  • Ana Luisa Anaya, Rachel Mata, James J Sims, Azucena González-Coloma, Rocio Cruz-Ortega, Ana Guadaño, Blanca E Hernández-Bautista, Sharon L Midland, Riselda Ríos, Arturo Gómez-Pompa. Allelochemical potential of Callicarpa acuminata. Journal of chemical ecology. 2003 Dec; 29(12):2761-76. doi: 10.1023/b:joec.0000008019.22063.5c. [PMID: 14969362]
  • Zulema Cantillo-Ciau, Gonzalo J Mena-Rejón, Esther Quintero-Mármol, Antonio Jiménez-Díaz, Leovigildo Quijano. Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Sep; 58(9-10):649-54. doi: 10.1515/znc-2003-9-1009. [PMID: 14577625]
  • Suresh Awale, Yasuhiro Tezuka, Arjun H Banskota, I Ketut Adnyana, Shigetoshi Kadota. Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity. Chemical & pharmaceutical bulletin. 2003 Mar; 51(3):268-75. doi: 10.1248/cpb.51.268. [PMID: 12612410]
  • Yuji Imaizumi, Kazuho Sakamoto, Aki Yamada, Aya Hotta, Susumu Ohya, Katsuhiko Muraki, Masanobu Uchiyama, Tomohiko Ohwada. Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit. Molecular pharmacology. 2002 Oct; 62(4):836-46. doi: 10.1124/mol.62.4.836. [PMID: 12237330]
  • Ammanamanchi S R Anjaneyulu, Vallurupalli Anjaneyulu, Vadali Lakshmana Rao. New beyerane and isopimarane diterpenoids from Rhizophora mucronata. Journal of Asian natural products research. 2002 Mar; 4(1):53-61. doi: 10.1080/10286020290019703. [PMID: 11991193]
  • W G Duan, X P Chen, L L Wang, S Deng, Y H Zhou, X N An. [Analysis of main chemical composition in hydrogenated rosin from Zhuzhou]. Se pu = Chinese journal of chromatography. 2001 Jan; 19(1):78-81. doi: ". [PMID: 12541853]
  • H Hägerstrand, M Danieluk, M Bobrowska-Hägerstrand, A Iglic, A Wróbel, B Isomaa, M Nikinmaa. Influence of band 3 protein absence and skeletal structures on amphiphile- and Ca(2+)-induced shape alterations in erythrocytes: a study with lamprey (Lampetra fluviatilis), trout (Onchorhynchus mykiss) and human erythrocytes. Biochimica et biophysica acta. 2000 Jun; 1466(1-2):125-38. doi: 10.1016/s0005-2736(00)00184-x. [PMID: 10825437]
  • G E Fâhraeus-Van Ree, J F Payne. Enzyme cytochemical responses of mussels (Mytilus edulis) to resin acid constituents of pulp mill effluents. Bulletin of environmental contamination and toxicology. 1999 Oct; 63(4):430-7. doi: 10.1007/s001289900998. [PMID: 10501718]