(R)-Citronellal (BioDeep_00000000622)

 

Secondary id: BioDeep_00000863888

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(R)-(+)-Citronellal, technical grade, 90\\%

化学式: C10H18O (154.1358)
中文名称: (R)-(+)-香茅醛, (R)-(+)-香茅, -(+)-香茅醛, （R） -（+）-香茅醛
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 32.17%

分子结构信息

SMILES: C/C(C)=C\CC[C@@H](C)CC=O
InChI: InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1

描述信息

(R)-(+)-citronellal is the (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal). It is an enantiomer of a (S)-(-)-citronellal.
(R)-(+)-Citronellal is a natural product found in Litsea cubeba, Backhousia citriodora, and other organisms with data available.
(R)-Citronellal is found in citrus. (R)-Citronellal is a constituent of citronella oil. Also in citrus, lavender, eucalyptus oils and others. (R)-Citronellal is a flavouring agent
Constituent of citronella oiland is) also in citrus, lavender, eucalyptus oils and others. Flavouring agent. (R)-Citronellal is found in lemon balm, citrus, and herbs and spices.
The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).
(R)-(+)-Citronellal, isolated from citrus, lavender and eucalyptus oils, is a monoterpenoid and main component of citronellal oil with a distinct lemon scent. A flavouring agent. Used for insect repellent and antifungal properties[1][2].
(R)-(+)-Citronellal, isolated from citrus, lavender and eucalyptus oils, is a monoterpenoid and main component of citronellal oil with a distinct lemon scent. A flavouring agent. Used for insect repellent and antifungal properties[1][2].

同义名列表

27 个代谢物同义名

(R)-(+)-Citronellal, technical grade, 90\\%; 2,6-Dimethylhept-5-enecarboxaldehyde; 6-Octenal, 3,7-dimethyl-, (theta)-; 6-Octenal, 3,7-dimethyl-, (3R)-; 6-Octenal, 3,7-dimethyl-, (R)-; 3,7-Dimethyl-6-octenal, (3R)-; (3R)-3,7-dimethyloct-6-enal; 3,7-Dimethyl-(3R)-6-Octenal; (3R)-3,7-Dimethyl-6-octenal; (R)-3,7-Dimethyloct-6-enal; (R)-3,7-dimethyl-6-octenal; 3,7-dimethyloct-6-en-1-al; 3,7-Dimethyl-6-octenal; (3R)-(+)-citronellal; (R)-(+)-Citronellal; 2,3-Dihydrocitral; beta-Citronellal; (+)-Citronellal; (±)-Citronellal; (R)-citronellal; dl-Citronellal; d-Citronellal; β-Citronellal; Rhodinal; Citronellal; (R)-(+)-Citronellal; (R)-(+)-Citronellal



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

71 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 8 ABCB1, AXIN2, BCL2, CAT, HPGDS, PKM, PTGS2, SLC9A1
Peripheral membrane protein 3 ACHE, CYP1B1, PTGS2
Endoplasmic reticulum membrane 3 BCL2, CYP1B1, PTGS2
Nucleus 5 ACHE, AXIN2, BCL2, CS, PKM
cytosol 7 ANK1, AXIN2, BCL2, CAT, HPGDS, LIPE, PKM
centrosome 1 AXIN2
nucleoplasm 2 HPGDS, SLC9A1
Cell membrane 5 ABCB1, ACHE, LIPE, SLC9A1, TRPA1
lamellipodium 1 SLC9A1
Multi-pass membrane protein 4 ABCB1, CATSPER3, SLC9A1, TRPA1
Synapse 1 ACHE
cell surface 3 ABCB1, ACHE, SLC9A1
Golgi apparatus 2 ACHE, ATRN
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
sarcolemma 1 ANK1
Cytoplasm, cytosol 1 LIPE
acrosomal vesicle 1 CATSPER3
plasma membrane 8 ABCB1, ACHE, ANK1, ATRN, AXIN2, CATSPER3, SLC9A1, TRPA1
Membrane 10 ABCB1, ACHE, ANK1, BCL2, CAT, CS, CYP1B1, LIPE, SLC9A1, TRPA1
apical plasma membrane 2 ABCB1, SLC9A1
basolateral plasma membrane 2 ANK1, SLC9A1
caveola 2 LIPE, PTGS2
extracellular exosome 6 ABCB1, ATRN, CAT, CS, PKM, SLC9A1
endoplasmic reticulum 3 BCL2, CATSPER3, PTGS2
extracellular space 5 ACHE, ATRN, CXCL8, IL6, INS
perinuclear region of cytoplasm 2 ACHE, SLC9A1
intercalated disc 1 SLC9A1
mitochondrion 6 BCL2, CAT, CS, CYP1B1, PKM, SLC9A1
protein-containing complex 3 BCL2, CAT, PTGS2
intracellular membrane-bounded organelle 3 CAT, CYP1B1, HPGDS
Microsome membrane 2 CYP1B1, PTGS2
Single-pass type I membrane protein 1 ATRN
Secreted 4 ACHE, CXCL8, IL6, INS
extracellular region 6 ACHE, CAT, CXCL8, IL6, INS, PKM
cytoplasmic side of plasma membrane 1 ANK1
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
[Isoform 2]: Secreted 1 ATRN
Mitochondrion matrix 1 CS
mitochondrial matrix 2 CAT, CS
Extracellular side 1 ACHE
motile cilium 1 CATSPER3
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
Extracellular vesicle 1 PKM
T-tubule 1 SLC9A1
Z disc 1 ANK1
beta-catenin destruction complex 1 AXIN2
vesicle 1 PKM
postsynaptic membrane 1 ANK1
Apical cell membrane 1 ABCB1
Membrane raft 1 SLC9A1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 ANK1
focal adhesion 2 CAT, SLC9A1
axolemma 1 ANK1
Peroxisome 1 CAT
basement membrane 1 ACHE
sarcoplasmic reticulum 1 ANK1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 PKM
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 2 ANK1, PTGS2
cilium 1 PKM
stereocilium bundle 1 TRPA1
cytoskeleton 1 ANK1
Basolateral cell membrane 1 SLC9A1
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
M band 1 ANK1
Cell projection, cilium, flagellum membrane 1 CATSPER3
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 2 CAT, PKM
secretory granule lumen 3 CAT, INS, PKM
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
synaptic cleft 1 ACHE
external side of apical plasma membrane 1 ABCB1
[Isoform 1]: Cell membrane 1 ATRN
Rough endoplasmic reticulum 1 PKM
spectrin-associated cytoskeleton 1 ANK1
ankyrin-1 complex 1 ANK1
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
[Isoform Mu18]: Sarcoplasmic reticulum 1 ANK1
[Isoform Mu19]: Sarcoplasmic reticulum 1 ANK1
[Isoform Mu20]: Sarcoplasmic reticulum 1 ANK1
cation-transporting ATPase complex 1 SLC9A1
[Isoform H]: Cell membrane 1 ACHE
CatSper complex 1 CATSPER3


文献列表

  • Akshay Kumar, Tanya Singh Raghuvanshi, Surya Pratap, Horesh Kumar, Bhanu Prakash. Nanofabrication of citronellal with chitosan biopolymer to boost its efficacy against aflatoxin B1 and Aspergillus flavus mediated biodeterioration of active ingredient of Piper longum. Food chemistry. 2024 Aug; 449(?):139240. doi: 10.1016/j.foodchem.2024.139240. [PMID: 38599109]
  • Yue Qiu, Xue Zhang, Shan-Shan Li, Yin-Lan Li, Bing-Yan Mao, Jia-Xin Fan, Shuang-Guo, Ya-Ling Yin, Peng Li. Citronellal can alleviate vascular endothelial dysfunction by reducing ectopic miR-133a expression. Life sciences. 2024 Feb; 339(?):122382. doi: 10.1016/j.lfs.2023.122382. [PMID: 38154610]
  • Thomas Vanegas-Estévez, Fanny Melina Duque, Diana L Urbina, Luis C Vesga, Stelia C Mendez-Sanchez, Jonny E Duque. Design and elucidation of an insecticide from natural compounds targeting mitochondrial proteins of Aedes aegypti. Pesticide biochemistry and physiology. 2024 Jan; 198(?):105721. doi: 10.1016/j.pestbp.2023.105721. [PMID: 38225076]
  • Laure Martinelli, Camille Bihanic, Aurélie Bony, Florence Gros, Corentin Conart, Sébastien Fiorucci, Hervé Casabianca, Frédéric Schiets, Giorgiana Chietera, Benoît Boachon, Bernard Blerot, Sylvie Baudino, Frédéric Jullien, Denis Saint-Marcoux. Citronellol biosynthesis in pelargonium is a multi-step pathway involving PRISE enzymes. Plant physiology. 2023 Oct; ?(?):. doi: 10.1093/plphys/kiad550. [PMID: 37831417]
  • Nikola M Stojanović, Marko Z Mladenović, Pavle J Randjelović, Niko S Radulović. The potential of lemon balm (Melissa officinalis L.) essential oil as an anti-anxiety agent - is the citronellal the activity carrier?. Journal of ethnopharmacology. 2023 Oct; 314(?):116661. doi: 10.1016/j.jep.2023.116661. [PMID: 37207879]
  • Caroline Deweer, Karin Sahmer, Jérôme Muchembled. Anti-oomycete activities from essential oils and their major compounds on Phytophthora infestans. Environmental science and pollution research international. 2023 Oct; ?(?):. doi: 10.1007/s11356-023-29270-6. [PMID: 37779122]
  • Xi Yang, Chunzhe Jin, Ziwei Wu, Hui Han, Zhilin Zhang, Yongjian Xie, Dayu Zhang. Toxicity and Physiological Effects of Nine Lamiaceae Essential Oils and Their Major Compounds on Reticulitermes dabieshanensis. Molecules (Basel, Switzerland). 2023 Feb; 28(5):. doi: 10.3390/molecules28052007. [PMID: 36903258]
  • Haneen Ibrahim Al Othman, Atiqah Zaid, Francesco Cacciola, Zhijun Zhao, Xiaosheng Guan, Jalal T Althakafy, Yong Foo Wong. Evaluation of Cryogen-Free Thermal Modulation-Based Enantioselective Comprehensive Two-Dimensional Gas Chromatography for Stereo-Differentiation of Monoterpenes in Citrus spp. Leaf Oils. Molecules (Basel, Switzerland). 2023 Feb; 28(3):. doi: 10.3390/molecules28031381. [PMID: 36771047]
  • A O C Costa, R I A Rego, H H N Andrade, T K V L Costa, M G S S Salvadori, R N Almeida, R D Castro. Evaluation of the antinociceptive effect generated by citronellal monoterpene isomers. Brazilian journal of biology = Revista brasleira de biologia. 2023; 83(?):e271781. doi: 10.1590/1519-6984.271781. [PMID: 37255202]
  • Desmond O Agwunobi, Min Wang, Zihao Wang, Ruwei Bai, Ruotong Wang, Qiuyu Hu, Zhijun Yu, Jingze Liu. The toxicity of the monoterpenes from lemongrass is mitigated by the detoxifying symbiosis of bacteria and fungi in the tick Haemaphysalis longicornis. Ecotoxicology and environmental safety. 2022 Dec; 247(?):114261. doi: 10.1016/j.ecoenv.2022.114261. [PMID: 36332404]
  • Immacolata Iovinella, Beniamino Caputo, Pietro Cobre, Mattia Manica, Alessandro Mandoli, Francesca Romana Dani. Advances in mosquito repellents: effectiveness of citronellal derivatives in laboratory and field trials. Pest management science. 2022 Dec; 78(12):5106-5112. doi: 10.1002/ps.7127. [PMID: 36102335]
  • Seyyed Morteza Hoseini, Ali Taheri Mirghaed, Esmail Pagheh, Seyed Hossein Hoseinifar, Hien Van Doan. Anesthesia of rainbow trout with citronellal: Efficacy and biochemical effects. Journal of experimental zoology. Part A, Ecological and integrative physiology. 2022 03; 337(3):227-237. doi: 10.1002/jez.2560. [PMID: 34826206]
  • Nikola M Stojanović, Marko Z Mladenović, Aleksandra Maslovarić, Nenad I Stojiljković, Pavle J Randjelović, Niko S Radulović. Lemon balm (Melissa officinalis L.) essential oil and citronellal modulate anxiety-related symptoms - In vitro and in vivo studies. Journal of ethnopharmacology. 2022 Feb; 284(?):114788. doi: 10.1016/j.jep.2021.114788. [PMID: 34718102]
  • Xu Liu, Yue Qiu, Yanhua Liu, Ning Huang, Cai Hua, Qianqian Wang, Zeqing Wu, Junxiu Lu, Ping Song, Jian Xu, Peng Li, Yaling Yin. Citronellal ameliorates doxorubicin-induced hepatotoxicity via antioxidative stress, antiapoptosis, and proangiogenesis in rats. Journal of biochemical and molecular toxicology. 2021 Feb; 35(2):e22639. doi: 10.1002/jbt.22639. [PMID: 33051984]
  • Bagora Bayala, Ahmed Y Coulibaly, Florencia W Djigma, Bolni Marius Nagalo, Silvère Baron, Gilles Figueredo, Jean-Marc A Lobaccaro, Jacques Simpore. Chemical composition, antioxidant, anti-inflammatory and antiproliferative activities of the essential oil of Cymbopogon nardus, a plant used in traditional medicine. Biomolecular concepts. 2020 Apr; 11(1):86-96. doi: 10.1515/bmc-2020-0007. [PMID: 32304294]
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  • Khan Bilal Mukhtar Ahmed, M Masroor A Khan, Ajmat Jahan, Husna Siddiqui, Moin Uddin. Gamma rays induced acquisition of structural modification in chitosan boosts photosynthetic machinery, enzymatic activities and essential oil production in citronella grass (Cymbopogon winterianus Jowitt). International journal of biological macromolecules. 2020 Feb; 145(?):372-389. doi: 10.1016/j.ijbiomac.2019.12.130. [PMID: 31862372]
  • Abeer A Mohamed, Said I Behiry, Hosny A Younes, Nader A Ashmawy, Mohamed Z M Salem, Ofelia Márquez-Molina, Alberto Barbabosa-Pilego. Antibacterial activity of three essential oils and some monoterpenes against Ralstonia solanacearum phylotype II isolated from potato. Microbial pathogenesis. 2019 Oct; 135(?):103604. doi: 10.1016/j.micpath.2019.103604. [PMID: 31247257]
  • Laurence Lins, Simon Dal Maso, Berenice Foncoux, Anouar Kamili, Yoann Laurin, Manon Genva, M Haissam Jijakli, Caroline De Clerck, Marie Laure Fauconnier, Magali Deleu. Insights into the Relationships Between Herbicide Activities, Molecular Structure and Membrane Interaction of Cinnamon and Citronella Essential Oils Components. International journal of molecular sciences. 2019 Aug; 20(16):. doi: 10.3390/ijms20164007. [PMID: 31426453]
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  • Akanksha Singh, Rupali Gupta, Sudeep Tandon, Prateeksha, Rakesh Pandey. Anti-biofilm and anti-virulence potential of 3,7-dimethyloct-6-enal derived from Citrus hystrix against bacterial blight of rice caused by Xanthomonas oryzae pv. oryzae. Microbial pathogenesis. 2018 Feb; 115(?):264-271. doi: 10.1016/j.micpath.2017.12.051. [PMID: 29273511]
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  • Ki-Suk Kim, In-Seung Lee, Kang-Hoon Kim, Jiyoung Park, Yumi Kim, Jeong-Hee Choi, Jin-Sung Choi, Hyeung-Jin Jang. Activation of intestinal olfactory receptor stimulates glucagon-like peptide-1 secretion in enteroendocrine cells and attenuates hyperglycemia in type 2 diabetic mice. Scientific reports. 2017 10; 7(1):13978. doi: 10.1038/s41598-017-14086-5. [PMID: 29070885]
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  • Eun Jo Du, Tae Jung Ahn, Min Sung Choi, Ilmin Kwon, Hyung-Wook Kim, Jae Young Kwon, KyeongJin Kang. The Mosquito Repellent Citronellal Directly Potentiates Drosophila TRPA1, Facilitating Feeding Suppression. Molecules and cells. 2015 Oct; 38(10):911-7. doi: 10.14348/molcells.2015.0215. [PMID: 26447139]
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  • Francine Novack Victoria, Roberta Anversa, Filipe Penteado, Micheli Castro, Eder João Lenardão, Lucielli Savegnago. Antioxidant and antidepressant-like activities of semi-synthetic α-phenylseleno citronellal. European journal of pharmacology. 2014 Nov; 742(?):131-8. doi: 10.1016/j.ejphar.2014.09.005. [PMID: 25218989]
  • Akbar Ali, M Masroor A Khan, Moin Uddin, M Naeem, Mohd Idrees, Nadeem Hashmi, Tariq Ahmad Dar, Lalit Varshney. Radiolytically depolymerized sodium alginate improves physiological activities, yield attributes and composition of essential oil of Eucalyptus citriodora Hook. Carbohydrate polymers. 2014 Nov; 112(?):134-44. doi: 10.1016/j.carbpol.2014.05.070. [PMID: 25129727]
  • J C Ribeiro, W L C Ribeiro, A L F Camurça-Vasconcelos, I T F Macedo, J M L Santos, H C B Paula, J V Araújo Filho, R D Magalhães, C M L Bevilaqua. Efficacy of free and nanoencapsulated Eucalyptus citriodora essential oils on sheep gastrointestinal nematodes and toxicity for mice. Veterinary parasitology. 2014 Aug; 204(3-4):243-8. doi: 10.1016/j.vetpar.2014.05.026. [PMID: 24929446]
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  • Osnat Altshuler, Mohamad Abu-Abied, David Chaimovitsh, Alona Shechter, Hilla Frucht, Nativ Dudai, Einat Sadot. Enantioselective effects of (+)- and (-)-citronellal on animal and plant microtubules. Journal of natural products. 2013 Sep; 76(9):1598-604. doi: 10.1021/np4002702. [PMID: 23947826]
  • Marilia Trindade de Santana, Makson Gleydson Brito de Oliveira, Michele Fraga Santana, Damião Pergentino De Sousa, Danielle Gomes Santana, Enilton Aparecido Camargo, Aldeídia Pereira de Oliveira, Jackson Roberto Guedes da Silva Almeida, Lucindo José Quintans-Júnior. Citronellal, a monoterpene present in Java citronella oil, attenuates mechanical nociception response in mice. Pharmaceutical biology. 2013 Sep; 51(9):1144-9. doi: 10.3109/13880209.2013.781656. [PMID: 23795810]
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