Dehydroabietic acid (BioDeep_00000003799)

Main id: BioDeep_00000229910

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

化学式: C20H28O2 (300.2089)
中文名称: 脱氢枞酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1c2c(cc(c1)C(C)C)CC[C@@H]1[C@@]2(CCC[C@@]1(C)C(=O)O)C
InChI: InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)

描述信息

Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
Dehydroabietic acid possesses antiviral activity[1].
Dehydroabietic acid possesses antiviral activity[1].

同义名列表

14 个代谢物同义名

(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid; 1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid; 1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylate; 1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid; 13-Isopropylpodocarpa-8,11,13-trien-15-oic acid; 13-Isopropylpodocarpa-8,11,13-trien-15-Oate; Abieta-8,11,13-trien-18-oic acid; Abieta-8,11,13-trien-18-Oate; (+)-Dehydroabietic acid; (-)-Dehydroabietic acid; (-)-Dehydroabietate; Dehydroabietic acid; Dehydroabietate; Dehydroabietic acid



数据库引用编号

24 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)

175 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。

亚细胞结构定位 关联基因列表
Cytoplasm 10 ALB, ANXA5, BCL2, CASP3, CASP8, CASP9, NOS3, PIK3CA, PPARG, TUBB4B
Peripheral membrane protein 1 ANXA5
Endosome membrane 1 NOTCH1
Endoplasmic reticulum membrane 2 BCL2, NOTCH1
Nucleus 11 ALB, BCL2, CASP3, CASP8, CASP9, GPX4, JUND, NOS3, NOTCH1, PPARG, TUBB4B
cytosol 12 ALB, ANXA5, BCL2, CASP3, CASP8, CASP9, GPX4, NOS3, NOTCH1, PIK3CA, PPARG, TUBB4B
centrosome 1 ALB
nucleoplasm 6 CASP3, CASP8, JUND, NOS3, NOTCH1, PPARG
RNA polymerase II transcription regulator complex 2 JUND, PPARG
Cell membrane 3 KCNMA1, NOTCH1, TNF
lamellipodium 2 CASP8, PIK3CA
Multi-pass membrane protein 2 KCNA3, KCNMA1
cell surface 3 ADIPOQ, NOTCH1, TNF
glutamatergic synapse 3 CASP3, KCNA3, NOTCH1
Golgi apparatus 2 ALB, NOS3
Golgi membrane 3 INS, NOS3, NOTCH1
neuronal cell body 2 CASP3, TNF
presynaptic membrane 1 KCNA3
sarcolemma 1 ANXA5
acrosomal vesicle 1 NOTCH1
plasma membrane 6 KCNA3, KCNMA1, NOS3, NOTCH1, PIK3CA, TNF
Membrane 5 ANXA5, BCL2, KCNA3, KCNMA1, NOTCH1
apical plasma membrane 2 KCNMA1, NOTCH1
axon 2 CCK, KCNA3
caveola 2 KCNMA1, NOS3
extracellular exosome 4 ALB, ANXA5, GPX4, TUBB4B
endoplasmic reticulum 4 ADIPOQ, ALB, BCL2, NOTCH1
extracellular space 6 ADIPOQ, ALB, CCK, CCL2, INS, TNF
perinuclear region of cytoplasm 4 KCNA3, NOS3, PIK3CA, PPARG
Schaffer collateral - CA1 synapse 1 NOTCH1
adherens junction 1 NOTCH1
intercalated disc 1 PIK3CA
mitochondrion 4 BCL2, CASP8, CASP9, GPX4
protein-containing complex 5 ALB, BCL2, CASP8, CASP9, GPX4
intracellular membrane-bounded organelle 1 PPARG
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 NOTCH1
Secreted 5 ADIPOQ, ALB, CCK, CCL2, INS
extracellular region 9 ADIPOQ, ALB, ANXA5, CCK, CCL2, INS, NOTCH1, TNF, TUBB4B
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, CASP8
anchoring junction 1 ALB
transcription regulator complex 1 JUND
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, TNF
Extracellular vesicle 1 TUBB4B
microtubule cytoskeleton 1 TUBB4B
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 KCNA3, KCNMA1
Cell projection, lamellipodium 1 CASP8
Membrane raft 2 KCNA3, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TUBB4B
focal adhesion 1 ANXA5
microtubule 1 TUBB4B
collagen trimer 1 ADIPOQ
collagen-containing extracellular matrix 2 ADIPOQ, ANXA5
receptor complex 2 NOTCH1, PPARG
Zymogen granule membrane 1 ANXA5
ciliary basal body 1 ALB
chromatin 2 JUND, PPARG
Late endosome membrane 1 NOTCH1
phagocytic cup 1 TNF
mitotic spindle 1 TUBB4B
cytoskeleton 3 CASP8, NOS3, TUBB4B
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
[Isoform 2]: Cell membrane 1 KCNA3
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
nuclear envelope 1 GPX4
endosome lumen 1 INS
axonemal microtubule 1 TUBB4B
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
cell body 1 CASP8
myelin sheath 1 BCL2
voltage-gated potassium channel complex 2 KCNA3, KCNMA1
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 ALB, INS
transcription repressor complex 1 JUND
platelet alpha granule lumen 1 ALB
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
azurophil granule lumen 1 TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 NOTCH1
apoptosome 1 CASP9
calyx of Held 1 KCNA3
vesicle membrane 1 ANXA5
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
[Isoform 1]: Cell membrane 1 KCNA3
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Notch 1 intracellular domain]: Nucleus 1 NOTCH1
MAML1-RBP-Jkappa- ICN1 complex 1 NOTCH1
ciliary transition fiber 1 ALB
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Santiago Michavila Puente-Villegas, Luis Apaza Ticona, Ángel Rumbero Sánchez, José-Luis Acebes. Diterpenes of Pinus pinaster aiton with anti-inflammatory, analgesic, and antibacterial activities. Journal of ethnopharmacology. 2023 Aug; ?(?):117021. doi: 10.1016/j.jep.2023.117021. [PMID: 37567424]
  • Yifeng Zhang, Jie Gao, Lin Ma, Lichan Tu, Tianyuan Hu, Xiaoyi Wu, Ping Su, Yujun Zhao, Yuan Liu, Dan Li, Jiawei Zhou, Yan Yin, Yuru Tong, Huan Zhao, Yun Lu, Jiadian Wang, Wei Gao, Luqi Huang. Tandemly duplicated CYP82Ds catalyze 14-hydroxylation in triptolide biosynthesis and precursor production in Saccharomyces cerevisiae. Nature communications. 2023 02; 14(1):875. doi: 10.1038/s41467-023-36353-y. [PMID: 36797237]
  • Puying Qi, Na Wang, Taihong Zhang, Yumei Feng, Xiang Zhou, Dan Zeng, Jiao Meng, Liwei Liu, Linhong Jin, Song Yang. Anti-Virulence Strategy of Novel Dehydroabietic Acid Derivatives: Design, Synthesis, and Antibacterial Evaluation. International journal of molecular sciences. 2023 Feb; 24(3):. doi: 10.3390/ijms24032897. [PMID: 36769220]
  • Meng Hao, Jianwei Xu, Houpeng Wen, Jiawei Du, Shaoyong Zhang, Min Lv, Hui Xu. Recent Advances on Biological Activities and Structural Modifications of Dehydroabietic Acid. Toxins. 2022 09; 14(9):. doi: 10.3390/toxins14090632. [PMID: 36136570]
  • Junjie Zhang, Ming Zhang, Yuxuan Dong, Wanting Gu, Tong Liu, Xinwei Xing, Jie Song, Maogong Wang, Chunrui Han. Molecular Design, Supramolecular Assembly, and Excellent Dye Adsorption Capacity of Natural Rigid Dehydroabietic Acid-Tailored Amide Organogelators. Langmuir : the ACS journal of surfaces and colloids. 2022 07; 38(29):8918-8927. doi: 10.1021/acs.langmuir.2c01068. [PMID: 35819938]
  • Nguyen Duy Phan, Ashraf M Omar, Sijia Sun, Juthamart Maneenet, Dya Fita Dibwe, Mao Sato, Surya Kant Kalauni, Naoki Toyooka, Tsutomu Fujii, Suresh Awale. Abietane diterpenes from Abies spectabilis and their anti-pancreatic cancer activity against the MIA PaCa-2 cell line. Bioorganic & medicinal chemistry letters. 2022 06; 66(?):128723. doi: 10.1016/j.bmcl.2022.128723. [PMID: 35395369]
  • Jiadian Wang, Ping Su, Linhui Gao, Yifeng Zhang, Jian Wang, Lichan Tu, Yujun Zhao, Yun Lu, Yan Yin, Luqi Huang, Wei Gao. A cytochrome P450 CYP81AM1 from Tripterygium wilfordii catalyses the C-15 hydroxylation of dehydroabietic acid. Planta. 2021 Oct; 254(5):95. doi: 10.1007/s00425-021-03743-9. [PMID: 34643823]
  • Gai Gao, Zhishen Xie, Er-Wen Li, Yong Yuan, Yu Fu, Pan Wang, Xiaowei Zhang, Yonghui Qiao, Jiangyan Xu, Christian Hölscher, Hui Wang, Zhenqiang Zhang. Dehydroabietic acid improves nonalcoholic fatty liver disease through activating the Keap1/Nrf2-ARE signaling pathway to reduce ferroptosis. Journal of natural medicines. 2021 Jun; 75(3):540-552. doi: 10.1007/s11418-021-01491-4. [PMID: 33590347]
  • Bao-Li Fei, Chun-Nuan Hui, Zuzhuang Wei, Ling-Yan Kong, Jian-Ying Long, Chunhua Qiao, Zhen-Feng Chen. Copper(II) and iron(III) complexes of chiral dehydroabietic acid derived from natural rosin: metal effect on structure and cytotoxicity. Metallomics : integrated biometal science. 2021 04; 13(4):. doi: 10.1093/mtomcs/mfab014. [PMID: 33765148]
  • Lin-Ying Li, Bao-Li Fei, Pingping Wang, Ling-Yan Kong, Jian-Ying Long. Discovery of novel dehydroabietic acid derivatives as DNA/BSA binding and anticancer agents. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2021 Feb; 246(?):118944. doi: 10.1016/j.saa.2020.118944. [PMID: 33007643]
  • Rosario Schicchi, Anna Geraci, Sergio Rosselli, Alberto Spinella, Antonella Maggio, Maurizio Bruno. Phytochemical investigation of the needles of Abies nebrodensis (Lojac.) Mattei. Natural product research. 2020 Aug; 34(15):2131-2136. doi: 10.1080/14786419.2019.1576044. [PMID: 30873863]
  • Zhishen Xie, Gai Gao, Hui Wang, Erwen Li, Yong Yuan, Jiangyan Xu, Zhenqiang Zhang, Pan Wang, Yu Fu, Huahui Zeng, Junying Song, Christian Hölscher, Hui Chen. Dehydroabietic acid alleviates high fat diet-induced insulin resistance and hepatic steatosis through dual activation of PPAR-γ and PPAR-α. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Jul; 127(?):110155. doi: 10.1016/j.biopha.2020.110155. [PMID: 32413669]
  • Reina Omura, Junko Sowa-Osako, Chiharu Tateishi, Ayaka Okazaki, Kazuyoshi Fukai, Tsuyoshi Kawakami, Maiko Tahara, Daisuke Tsuruta. Allergic contact dermatitis to abietic acid derivatives in an over-the-counter hydrocolloid dressing. Contact dermatitis. 2020 May; 82(5):309-310. doi: 10.1111/cod.13461. [PMID: 31891190]
  • Lichan Tu, Ping Su, Zhongren Zhang, Linhui Gao, Jiadian Wang, Tianyuan Hu, Jiawei Zhou, Yifeng Zhang, Yujun Zhao, Yuan Liu, Yadi Song, Yuru Tong, Yun Lu, Jian Yang, Cao Xu, Meirong Jia, Reuben J Peters, Luqi Huang, Wei Gao. Genome of Tripterygium wilfordii and identification of cytochrome P450 involved in triptolide biosynthesis. Nature communications. 2020 02; 11(1):971. doi: 10.1038/s41467-020-14776-1. [PMID: 32080175]
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  • Kostas Ioannidis, Eleni Melliou, Prokopios Magiatis. High-Throughput 1H-Nuclear Magnetic Resonance-Based Screening for the Identification and Quantification of Heartwood Diterpenic Acids in Four Black Pine (Pinus nigra Arn.) Marginal Provenances in Greece. Molecules (Basel, Switzerland). 2019 Oct; 24(19):. doi: 10.3390/molecules24193603. [PMID: 31591296]
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  • Malin Silverå Ejneby, Xiongyu Wu, Nina E Ottosson, E Peter Münger, Ingemar Lundström, Peter Konradsson, Fredrik Elinder. Atom-by-atom tuning of the electrostatic potassium-channel modulator dehydroabietic acid. The Journal of general physiology. 2018 05; 150(5):731-750. doi: 10.1085/jgp.201711965. [PMID: 29626041]
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  • Hyun-Woo Oh, Chan-Seok Yun, Jun Hyoung Jeon, Ji-Ae Kim, Doo-Sang Park, Hyung Won Ryu, Sei-Ryang Oh, Hyuk-Hwan Song, Yunhee Shin, Chan Sik Jung, Sang Woon Shin. Conifer Diterpene Resin Acids Disrupt Juvenile Hormone-Mediated Endocrine Regulation in the Indian Meal Moth Plodia interpunctella. Journal of chemical ecology. 2017 Jul; 43(7):703-711. doi: 10.1007/s10886-017-0861-9. [PMID: 28674826]
  • Victor Forman, Roberta Callari, Christophe Folly, Harald Heider, Björn Hamberger. Production of Putative Diterpene Carboxylic Acid Intermediates of Triptolide in Yeast. Molecules (Basel, Switzerland). 2017 Jun; 22(6):. doi: 10.3390/molecules22060981. [PMID: 28608823]
  • Fahimeh Moradi-Afrapoli, Samad Nejad Ebrahimi, Martin Smiesko, Matthias Hamburger. HPLC-Based Activity Profiling for GABAA Receptor Modulators in Extracts: Validation of an Approach Utilizing a Larval Zebrafish Locomotor Assay. Journal of natural products. 2017 05; 80(5):1548-1557. doi: 10.1021/acs.jnatprod.7b00081. [PMID: 28485933]
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  • Maria Sofia Costa, Adriana Rego, Vitor Ramos, Tiago B Afonso, Sara Freitas, Marco Preto, Viviana Lopes, Vitor Vasconcelos, Catarina Magalhães, Pedro N Leão. The conifer biomarkers dehydroabietic and abietic acids are widespread in Cyanobacteria. Scientific reports. 2016 Mar; 6(?):23436. doi: 10.1038/srep23436. [PMID: 26996104]
  • Chung Sub Kim, Lalita Subedi, Sun Yeou Kim, Sang Un Choi, Ki Hyun Kim, Kang Ro Lee. Diterpenes from the Trunk of Abies holophylla and Their Potential Neuroprotective and Anti-inflammatory Activities. Journal of natural products. 2016 Feb; 79(2):387-94. doi: 10.1021/acs.jnatprod.5b01053. [PMID: 26812172]
  • Dongjun Luo, Qing Ni, Anlai Ji, Wen Gu, Junhua Wu, Chunping Jiang. Dehydroabietic Acid Derivative QC4 Induces Gastric Cancer Cell Death via Oncosis and Apoptosis. BioMed research international. 2016; 2016(?):2581061. doi: 10.1155/2016/2581061. [PMID: 27057539]
  • Abir Nachar, Ammar Saleem, John T Arnason, Pierre S Haddad. Regulation of liver cell glucose homeostasis by dehydroabietic acid, abietic acid and squalene isolated from balsam fir (Abies balsamea (L.) Mill.) a plant of the Eastern James Bay Cree traditional pharmacopeia. Phytochemistry. 2015 Sep; 117(?):373-379. doi: 10.1016/j.phytochem.2015.07.001. [PMID: 26164238]
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  • Sandro Donizete Caetano da Silva, Maria Gorete Mendes de Souza, Miguel Jorge Oliveira Cardoso, Thais da Silva Moraes, Sérgio Ricardo Ambrósio, Rodrigo Cássio Sola Veneziani, Carlos Henrique G Martins. Antibacterial activity of Pinus elliottii against anaerobic bacteria present in primary endodontic infections. Anaerobe. 2014 Dec; 30(?):146-52. doi: 10.1016/j.anaerobe.2014.09.013. [PMID: 25270831]
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  • Wenyan Gao, Xiaoyan Dong, Nan Xie, Chunlan Zhou, Yuhua Fan, Guoyou Chen, Yanming Wang, Taiming Wei, Daling Zhu. Dehydroabietic acid isolated from Commiphora opobalsamum causes endothelium-dependent relaxation of pulmonary artery via PI3K/Akt-eNOS signaling pathway. Molecules (Basel, Switzerland). 2014 Jun; 19(6):8503-17. doi: 10.3390/molecules19068503. [PMID: 24959678]
  • Z Pandelides, J Guchardi, D Holdway. Dehydroabietic acid (DHAA) alters metabolic enzyme activity and the effects of 17β-estradiol in rainbow trout (Oncorhynchus mykiss). Ecotoxicology and environmental safety. 2014 Mar; 101(?):168-76. doi: 10.1016/j.ecoenv.2013.11.027. [PMID: 24507142]
  • Guang Zhang, Chunping Jiang, Zhongxia Wang, Weibo Chen, Wen Gu, Yitao Ding. Dehydroabietic acid derivative QC2 induces oncosis in hepatocellular carcinoma cells. BioMed research international. 2014; 2014(?):682197. doi: 10.1155/2014/682197. [PMID: 25110686]
  • Yanhong Xing, Wei Zhang, Jingjing Song, Yixin Zhang, Xianxing Jiang, Rui Wang. Anticancer effects of a novel class rosin-derivatives with different mechanisms. Bioorganic & medicinal chemistry letters. 2013 Jul; 23(13):3868-72. doi: 10.1016/j.bmcl.2013.04.069. [PMID: 23707051]
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