Indoleacrylic acid (BioDeep_00000027639)

 

Secondary id: BioDeep_00000001356, BioDeep_00000264828, BioDeep_00000405353

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


(2E)-3-(1H-indol-3-yl)prop-2-enoic acid

化学式: C11H9NO2 (187.0633)
中文名称: 3-吲哚丙烯酸, 反式-3-吲哚丙烯酸, 吲哚丙烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 28.49%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Indoleacrylic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/indoleacrylic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000027639). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CN2)C=CC(=O)O
InChI: InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+

描述信息

Indoleacrylic acid (CAS: 1204-06-4), also known as indoleacrylate, IA, and IAcrA, is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indoleacrylic acid is practically insoluble (in water) and a weak acidic compound (based on its pKa). Within the cell, indoleacrylic acid is primarily located in the membrane (predicted from logP). Indoleacrylic acid is best known as a plant growth hormone (a natural auxin), whereas its biological role in animals is still unknown. A two-stage production of this compound is likely: intestinal microorganisms catabolize tryptophan to indole derivatives which are then absorbed and converted into indoleacrylic acid and its glycine conjugate, indolylacryloylglycine (IAcrGly). Indolylacryloylglycine excretion in urine is especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy (PMID: 10707769). It has been recently found that indoleacrylic acid promotes intestinal epithelial barrier function and mitigates inflammatory responses. Stimulating indoleacrylic acid production could promote anti-inflammatory responses and have therapeutic benefits (PMID: 28704649). Urinary Indole-3-acrylate is produced by Clostridium sporogenes (PMID: 29168502). Indoleacrylic acid is also a metabolite of Peptostreptococcus (PMID: 28704649, 29168502).
trans-3-Indoleacrylic acid is an endogenous metabolite.

同义名列表

41 个代谢物同义名

(2E)-3-(1H-indol-3-yl)prop-2-enoic acid; (2E)-3-(1H-indol-3-yl)-2-Propenoic acid; (e)-3-(1H-indol-3-yl)Prop-2-enoic acid; (e)-3-(1H-indol-3-yl)-2-Propenoic acid; 3-(1H-indol-3-yl)-2-Propenoic acid; 3-(indol-3-yl)Prop-2-enoic acid; Indoleacrylic acid, sodium salt; Indoleacrylic acid, (e)-isomer; trans-beta-Indoleacrylic acid; 3-(1H-indol-3-yl)Acrylic acid; trans-3-Indoleacrylic acid; trans-Β-indoleacrylic acid; trans-b-Indoleacrylic acid; (e)-3-(indol-3-yl)Acrylate; trans-beta-Indoleacrylate; (e)-Indole-3-acrylic acid; 3-(3-Indolyl)acrylic acid; 3-beta-Indoleacrylic acid; Indole-3beta-acrylic acid; Indole-3β-acrylic acid; trans-b-Indoleacrylate; 3-Β-indoleacrylic acid; Indole-3b-acrylic acid; trans-3-Indoleacrylate; trans-Β-indoleacrylate; 3-Indolylacrylic acid; Indole-3-acrylic acid; Indole-3beta-acrylate; 3-(3-Indolyl)acrylate; 3-Indoleacrylic acid; Indole acrylic acid; Indole-3β-acrylate; Indole-3b-acrylate; Indoleacrylic acid; Indole-3-acrylate; 3-Indolylacrylate; 3-Indoleacrylate; Indoleacrylate; IAcrA; IA; Indoleacrylic acid



数据库引用编号

13 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)

8 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, AIFM2, ALDH1A3, CEP104, GFAP, IL13, NEFL
Mitochondrion membrane 1 AIFM2
Nucleus 2 AHR, AIFM2
cytosol 5 AHR, AIFM2, ALDH1A3, GFAP, NEFL
centrosome 1 CEP104
nucleoplasm 1 AHR
Cell membrane 3 AIFM2, CLEC4D, TNF
Lipid-anchor 1 AIFM2
Cell projection, axon 1 NEFL
Multi-pass membrane protein 1 RHO
cell surface 1 TNF
Golgi apparatus 1 RHO
Golgi membrane 2 INS, RHO
growth cone 1 NEFL
neuromuscular junction 1 NEFL
neuronal cell body 1 TNF
plasma membrane 6 AIFM2, CLEC4D, F2, IGHE, RHO, TNF
Membrane 2 CLEC4D, RHO
axon 1 NEFL
extracellular exosome 2 ALDH1A3, F2
extracellular space 11 AIFM2, F2, IGHE, IL10, IL13, IL17A, IL22, IL4, IL5, INS, TNF
Schaffer collateral - CA1 synapse 1 NEFL
mitochondrion 1 AIFM2
protein-containing complex 1 AHR
Single-pass type I membrane protein 1 IGHE
Secreted 8 F2, IL10, IL13, IL17A, IL22, IL4, IL5, INS
extracellular region 10 F2, IGHE, IL10, IL13, IL17A, IL22, IL4, IL5, INS, TNF
mitochondrial outer membrane 1 AIFM2
astrocyte end-foot 1 GFAP
transcription regulator complex 1 AHR
Cell projection, cilium 1 CEP104
ciliary membrane 1 RHO
photoreceptor inner segment 1 RHO
photoreceptor outer segment 1 RHO
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CEP104
external side of plasma membrane 4 CLEC4D, IL13, IL17A, TNF
axon cytoplasm 1 NEFL
cell-cell junction 1 RHO
recycling endosome 1 TNF
Single-pass type II membrane protein 2 CLEC4D, TNF
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 NEFL
collagen-containing extracellular matrix 1 F2
intermediate filament 2 GFAP, NEFL
cilium 1 CEP104
chromatin 1 AHR
IgE immunoglobulin complex 1 IGHE
cell projection 1 GFAP
phagocytic cup 1 TNF
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriole 1 CEP104
centriole 1 CEP104
Cell projection, cilium, photoreceptor outer segment 1 RHO
spindle pole 1 CEP104
blood microparticle 1 F2
sperm midpiece 1 RHO
[Isoform 2]: Cell membrane 1 IGHE
endosome lumen 1 INS
Lipid droplet 1 AIFM2
aryl hydrocarbon receptor complex 1 AHR
specific granule membrane 1 CLEC4D
tertiary granule membrane 1 CLEC4D
Golgi-associated vesicle membrane 1 RHO
cell body 1 GFAP
intermediate filament cytoskeleton 1 GFAP
secretory granule lumen 1 INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 2 F2, INS
Photoreceptor inner segment membrane 1 RHO
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
neurofilament 1 NEFL
ficolin-1-rich granule membrane 1 CLEC4D
photoreceptor outer segment membrane 1 RHO
sperm head plasma membrane 1 RHO
[Isoform 3]: Cell membrane 1 IGHE
cytoplasmic side of lysosomal membrane 1 GFAP
photoreceptor disc membrane 1 RHO
cholinergic synapse 1 NEFL
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
postsynaptic intermediate filament cytoskeleton 1 NEFL
presynaptic intermediate filament cytoskeleton 1 NEFL
rod photoreceptor outer segment 1 RHO
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Jing Hu, Kokoette Effiong, Muyuan Liu, Xi Xiao. Broad spectrum and species specificity of plant allelochemicals 1,2-benzenediol and 3-indoleacrylic acid against marine and freshwater harmful algae. The Science of the total environment. 2023 Nov; 898(?):166356. doi: 10.1016/j.scitotenv.2023.166356. [PMID: 37595905]
  • Kun Shi, Qiong Wang, Yao Su, Xingcui Xuan, Yaqiong Liu, Weiwei Chen, Yuanmin Qian, Gendie E Lash. Identification and functional analyses of differentially expressed metabolites in early stage endometrial carcinoma. Cancer science. 2018 Apr; 109(4):1032-1043. doi: 10.1111/cas.13532. [PMID: 29436067]
  • Xiaoyan Gao, Mingxing Guo, Baosheng Zhao, Long Peng, Jiankun Su, Xu Bai, Jun Li, Yanjiang Qiao. A urinary metabonomics study on biochemical changes in yeast-induced pyrexia rats: a new approach to elucidating the biochemical basis of the febrile response. Chemico-biological interactions. 2013 Jun; 204(1):39-48. doi: 10.1016/j.cbi.2013.04.001. [PMID: 23583517]
  • Pratibha Vyas, Robin Joshi, K C Sharma, Praveen Rahi, Ashu Gulati, Arvind Gulati. Cold-adapted and rhizosphere-competent strain of Rahnella sp. with broad-spectrum plant growth-promotion potential. Journal of microbiology and biotechnology. 2010 Dec; 20(12):1724-34. doi: . [PMID: 21193830]
  • Indeok Hwang, Soo Young Kim, Cheol Soo Kim, Yoonkyung Park, Giri Raj Tripathi, Seong-Ki Kim, Hyeonsook Cheong. Over-expression of the IGI1 leading to altered shoot-branching development related to MAX pathway in Arabidopsis. Plant molecular biology. 2010 Aug; 73(6):629-41. doi: 10.1007/s11103-010-9645-0. [PMID: 20473553]
  • J G Bell, J R Sargent, D R Tocher, J R Dick. Red blood cell fatty acid compositions in a patient with autistic spectrum disorder: a characteristic abnormality in neurodevelopmental disorders?. Prostaglandins, leukotrienes, and essential fatty acids. 2000 Jul; 63(1-2):21-5. doi: 10.1054/plef.2000.0186. [PMID: 10970708]
  • E Marklová. Where does indolylacrylic acid come from?. Amino acids. 1999; 17(4):401-13. doi: 10.1007/bf01361665. [PMID: 10707769]
  • E Marklová, L Mandel, L Jebavý, I M Hais. [Metabolism of indolylacrylic acid. III. Effect of intestinal microbes on the excretion of indolylacryloylglycine in urine]. Sbornik vedeckych praci Lekarske fakulty Karlovy univerzity v Hradci Kralove. Supplementum. 1986; 29(4-5):451-5. doi: NULL. [PMID: 3326153]