Geranic acid (BioDeep_00000003128)

 

Secondary id: BioDeep_00001871810

human metabolite Endogenous natural product


代谢物信息卡片


(2E)-3,7-di­methyl­octa-2,6-di­enoic acid

化学式: C10H16O2 (168.115)
中文名称: 香叶酸, 3,7-二甲基辛-2,6-二烯酸酯
谱图信息: 最多检出来源 Homo sapiens(plant) 29.07%

分子结构信息

SMILES: C(/C=C(\C)/CC/C=C(\C)/C)(=O)O
InChI: InChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)

描述信息

Geranic acid, also known as 3,7-dimethylocta-2,6-dienoate or geranate, is a member of the class of compounds known as acyclic monoterpenoids. Acyclic monoterpenoids are monoterpenes that do not contain a cycle. Thus, geranic acid is considered to be a fatty acid lipid molecule. Geranic acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Geranic acid, or 3,7-dimethyl-2,6-octadienoic acid, is a pheromone used by some organisms. It is a double bond isomer of nerolic acid .
Geranic acid is found in cardamom. Geranic acid is present in petitgrain, lemongrass and other essential oil

同义名列表

16 个代谢物同义名

(2E)-3,7-di­methyl­octa-2,6-di­enoic acid; 2,6-Octadienoic acid, 3,7-dimethyl-; 3,7-Dimethyl-2E,6-octadienoic acid; 3,7-Dimethyl-2,6-octadienoic acid; 3,7-dimethylocta-2,6-dienoic acid; 3,7-Dimethylocta-2,6-dienoate; Geranic acid (6ci); trans-Geranic acid; Decaprenoic acid; trans-Geranate; Geranoic acid; Geranic acid; Geranate; FA 10:2; Geranic acid; 3,7-Dimethylocta-2,6-dienoate



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(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)

47 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 7 AHR, DLG1, ELANE, GAPDH, GPR119, SREBF1, TYR
Peripheral membrane protein 2 DLG1, GBA1
Endosome membrane 2 FFAR4, SLC6A4
Endoplasmic reticulum membrane 3 DLG1, MLANA, SREBF1
Nucleus 4 AHR, DLG1, GAPDH, SREBF1
cytosol 5 AHR, DLG1, ELANE, GAPDH, SREBF1
phagocytic vesicle 1 ELANE
trans-Golgi network 2 GBA1, MLANA
nucleoplasm 2 AHR, SREBF1
Cell membrane 6 DLG1, FFAR1, FFAR4, GPR55, SEMA4D, SLC6A4
Multi-pass membrane protein 6 FFAR1, FFAR4, GPR55, SLC5A1, SLC6A4, SREBF1
Golgi apparatus membrane 1 SREBF1
Synapse 2 DLG1, SLC6A4
cell junction 1 DLG1
cell surface 1 ELANE
glutamatergic synapse 1 DLG1
Golgi apparatus 3 DLG1, GBA1, MLANA
Golgi membrane 2 INS, SREBF1
lysosomal membrane 3 FFAR4, GAA, GBA1
neuromuscular junction 1 DLG1
presynaptic membrane 1 SLC6A4
sarcolemma 1 DLG1
Cytoplasm, cytosol 1 GAPDH
Lysosome 3 GAA, GBA1, TYR
Presynapse 1 SLC6A4
plasma membrane 12 DLG1, F2, FFAR1, FFAR4, GAA, GAPDH, GPR119, GPR55, MLANA, SEMA4D, SLC5A1, SLC6A4
Membrane 6 DLG1, GAA, GAPDH, GPR55, SEMA4D, SLC6A4
apical plasma membrane 2 DLG1, SLC5A1
basolateral plasma membrane 1 DLG1
extracellular exosome 7 DLG1, ELANE, F2, GAA, GAPDH, GBA1, SLC5A1
Lysosome membrane 3 FFAR4, GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 3 DLG1, GBA1, SREBF1
extracellular space 4 ELANE, F2, INS, SEMA4D
lysosomal lumen 2 GAA, GBA1
perinuclear region of cytoplasm 4 DLG1, GAPDH, SLC5A1, TYR
adherens junction 1 DLG1
bicellular tight junction 1 DLG1
intercalated disc 1 DLG1
protein-containing complex 2 AHR, SREBF1
intracellular membrane-bounded organelle 3 GAA, GAPDH, TYR
postsynaptic density 1 DLG1
Single-pass type I membrane protein 2 SEMA4D, TYR
Secreted 3 F2, GAA, INS
extracellular region 4 ELANE, F2, GAA, INS
cytoplasmic side of plasma membrane 1 DLG1
anchoring junction 1 DLG1
transcription regulator complex 1 AHR
ciliary membrane 1 FFAR4
nuclear membrane 1 GAPDH
microtubule cytoskeleton 1 GAPDH
Melanosome membrane 2 MLANA, TYR
Early endosome 1 SLC5A1
cell-cell junction 1 DLG1
Golgi-associated vesicle 1 TYR
vesicle 1 GAPDH
postsynaptic membrane 2 SEMA4D, SLC6A4
Apical cell membrane 2 DLG1, SLC5A1
Cell membrane, sarcolemma 1 DLG1
Cytoplasm, perinuclear region 1 GAPDH
Membrane raft 2 DLG1, SLC6A4
Cell junction, focal adhesion 1 SLC6A4
Cytoplasm, cytoskeleton 1 GAPDH
focal adhesion 1 SLC6A4
microtubule 1 DLG1
GABA-ergic synapse 1 SEMA4D
cis-Golgi network 1 GOLGA6A
basement membrane 1 DLG1
intracellular vesicle 1 SLC5A1
collagen-containing extracellular matrix 2 ELANE, F2
secretory granule 1 ELANE
lateral plasma membrane 1 DLG1
receptor complex 1 GPR119
Cell projection, neuron projection 1 SLC6A4
neuron projection 2 DLG1, SLC6A4
cilium 1 FFAR4
chromatin 2 AHR, SREBF1
cytoskeleton 1 GAPDH
brush border membrane 1 SLC5A1
blood microparticle 1 F2
Basolateral cell membrane 1 DLG1
[Isoform 2]: Cell membrane 1 FFAR4
nuclear envelope 1 SREBF1
Endomembrane system 1 SLC6A4
endosome lumen 1 INS
Lipid droplet 1 GAPDH
aryl hydrocarbon receptor complex 1 AHR
Cytoplasmic vesicle membrane 1 SREBF1
tertiary granule membrane 1 GAA
Melanosome 2 MLANA, TYR
Golgi cisterna membrane 1 GOLGA6A
synaptic membrane 1 DLG1
secretory granule lumen 1 INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 2 F2, INS
transcription repressor complex 1 ELANE
specific granule lumen 1 ELANE
endocytic vesicle 1 FFAR4
transport vesicle 1 INS
azurophil granule membrane 1 GAA
node of Ranvier 1 DLG1
azurophil granule lumen 1 ELANE
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 DLG1
immunological synapse 1 DLG1
ER to Golgi transport vesicle membrane 1 SREBF1
semaphorin receptor complex 1 SEMA4D
MPP7-DLG1-LIN7 complex 1 DLG1
ribonucleoprotein complex 1 GAPDH
ficolin-1-rich granule membrane 1 GAA
[Isoform 1]: Cell membrane 1 FFAR4
Cytoplasmic vesicle, phagosome 1 ELANE
GAIT complex 1 GAPDH
Cell projection, cilium membrane 1 FFAR4
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
myelin sheath abaxonal region 1 DLG1
autolysosome lumen 1 GAA
intracellular organelle 1 SLC5A1
cell projection membrane 1 DLG1
nuclear aryl hydrocarbon receptor complex 1 AHR
serotonergic synapse 1 SLC6A4
cytosolic aryl hydrocarbon receptor complex 1 AHR
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
Golgi cis cisterna 1 GOLGA6A
lateral loop 1 DLG1


文献列表

  • Ayako Sanekata, Atsushi Tanigawa, Kiyoshi Takoi, Yasuyuki Nakayama, Youichi Tsuchiya. Interesting Behavior of Geranic Acid during the Beer Brewing Process: Why Could Geranic Acid Remain at a Higher Level Only in the Beer Using Sorachi Ace Hops?. Journal of agricultural and food chemistry. 2023 Nov; ?(?):. doi: 10.1021/acs.jafc.3c04740. [PMID: 37962414]
  • Shixiang Pan, Wenhao Li, Yaoguo Qin, Zhaokai Yang, Yan Liu, Zhuo Shi, Cheng Qu, Chen Luo, Xinling Yang. Discovery of Novel Potential Aphid Repellents: Geranic Acid Esters Containing Substituted Aromatic Rings. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27185949. [PMID: 36144685]
  • Qin M Qi, Samir Mitragotri. Mechanistic study of transdermal delivery of macromolecules assisted by ionic liquids. Journal of controlled release : official journal of the Controlled Release Society. 2019 10; 311-312(?):162-169. doi: 10.1016/j.jconrel.2019.08.029. [PMID: 31465826]
  • Hajo Kries, Franziska Kellner, Mohamed Omar Kamileen, Sarah E O'Connor. Inverted stereocontrol of iridoid synthase in snapdragon. The Journal of biological chemistry. 2017 09; 292(35):14659-14667. doi: 10.1074/jbc.m117.800979. [PMID: 28701463]
  • Sujatha Ramasamy, Norhanom Abdul Wahab, Nurhayati Zainal Abidin, Sugumaran Manickam, Zubaidah Zakaria. Growth inhibition of human gynecologic and colon cancer cells by Phyllanthus watsonii through apoptosis induction. PloS one. 2012; 7(4):e34793. doi: 10.1371/journal.pone.0034793. [PMID: 22536331]
  • Christo Paul Preethy, Ramamoorthy Padmapriya, Vaiyapuri Subbarayan Periasamy, Anvarbatcha Riyasdeen, Suresh Srinag, Hanumanthappa Krishnamurthy, Ali Abdullah Alshatwi, Mohammad Abdulkader Akbarsha. Antiproliferative property of n-hexane and chloroform extracts of Anisomeles malabarica (L). R. Br. in HPV16-positive human cervical cancer cells. Journal of pharmacology & pharmacotherapeutics. 2012 Jan; 3(1):26-34. doi: 10.4103/0976-500x.92500. [PMID: 22368413]
  • Juri Battilana, Francesco Emanuelli, Giorgio Gambino, Ivana Gribaudo, Flavia Gasperi, Paul K Boss, Maria Stella Grando. Functional effect of grapevine 1-deoxy-D-xylulose 5-phosphate synthase substitution K284N on Muscat flavour formation. Journal of experimental botany. 2011 Nov; 62(15):5497-508. doi: 10.1093/jxb/err231. [PMID: 21868399]
  • Ting Yang, Geert Stoopen, Nasser Yalpani, Jacques Vervoort, Ric de Vos, Alessandra Voster, Francel W A Verstappen, Harro J Bouwmeester, Maarten A Jongsma. Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation patterns. Metabolic engineering. 2011 Jul; 13(4):414-25. doi: 10.1016/j.ymben.2011.01.011. [PMID: 21296182]
  • Qing Liu, Mohammad Majdi, Katarina Cankar, Miriam Goedbloed, Tatsiana Charnikhova, Francel W A Verstappen, Ric C H de Vos, Jules Beekwilder, Sander van der Krol, Harro J Bouwmeester. Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana. PloS one. 2011; 6(8):e23255. doi: 10.1371/journal.pone.0023255. [PMID: 21858047]
  • Toshiya Masuda, Yuka Odaka, Natsuko Ogawa, Katsuo Nakamoto, Hideki Kuninaga. Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus). Journal of agricultural and food chemistry. 2008 Jan; 56(2):597-601. doi: 10.1021/jf072893l. [PMID: 18081247]
  • Yu-Yun Hsiao, Wen-Chieh Tsai, Chang-Sheng Kuoh, Tian-Hsiang Huang, Hei-Chia Wang, Tian-Shung Wu, Yann-Lii Leu, Wen-Huei Chen, Hong-Hwa Chen. Comparison of transcripts in Phalaenopsis bellina and Phalaenopsis equestris (Orchidaceae) flowers to deduce monoterpene biosynthesis pathway. BMC plant biology. 2006 Jul; 6(?):14. doi: 10.1186/1471-2229-6-14. [PMID: 16836766]
  • Miklós Tóth, Lorenzo Furlan, Venyamin G Yatsynin, István Ujváry, István Szarukán, Zoltán Imrei, Till Tolasch, Wittko Francke, Werner Jossi. Identification of pheromones and optimization of bait composition for click beetle pests (Coleoptera: Elateridae) in Central and Western Europe. Pest management science. 2003 Apr; 59(4):417-25. doi: 10.1002/ps.629. [PMID: 12701702]
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