Abrine (BioDeep_00000000078)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoic acid

化学式: C12H14N2O2 (218.1055)
中文名称: L-红豆碱, 相思豆毒素, 相思豆碱, L-(+)-相思豆碱, 相思子碱, L-(+)-相思子碱, L-(+)-红豆碱
谱图信息: 最多检出来源 Homo sapiens(otcml) 17.51%

分子结构信息

SMILES: CNC(CC1=CNC2=CC=CC=C21)C(=O)O
InChI: InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)

描述信息

N(alpha)-methyl-L-tryptophan is a N-methyl-L-alpha-amino acid that is the N(alpha)-methyl derivative of L-tryptophan. It has a role as an Escherichia coli metabolite. It is a L-tryptophan derivative and a N-methyl-L-alpha-amino acid. It is a tautomer of a N(alpha)-methyl-L-tryptophan zwitterion.
N-Methyltryptophan is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
A N-methyl-L-alpha-amino acid that is the N(alpha)-methyl derivative of L-tryptophan.
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.216
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.210
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.211
L-(+)-Abrine, a lethal albumin found in Abrus precatorius seeds, is an acute toxic alkaloid and chemical marker for abrin.
L-(+)-Abrine, a lethal albumin found in Abrus precatorius seeds, is an acute toxic alkaloid and chemical marker for abrin.

同义名列表

32 个代谢物同义名

(2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoic acid; (2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate; (S)-3-(1H-Indol-3-yl)-2-(methylamino)propanoic acid; Nalpha-Methyl-L-tryptophan, purum, >=98.0\\% (TLC); (S)-3-(1H-indol-3-yl)-2-methylaminopropionic acid; (2S)-3-indol-3-yl-2-(methylamino)propanoic acid; Nalpha-Methyl-L-tryptophan, analytical standard; N(alpha)-methyl-L-tryptophan; Nalpha-Methyl-L-tryptophan; L-Tryptophan, N-methyl-; N-a-Methyl-L-tryptophan; N-Methyl-L-tryptophane; N-Methyl-L-tryptophan; N-Metil-L-triptofano; L-N-methyltryptophan; N-methyl tryptophan; methyl-l-tryptophan; n-methyl-tryptophan; N-methyltryptophan; UNII-P57TWL22IX; L-Abrine, 99\\%; L-(+)-Abrine; ABRINE [MI]; P57TWL22IX; H-MeTrp-OH; L-Abrine; Abrine; E9M; N-Me-Trp-OH; Abrine; N-α-Methyl-L-tryptophan; Abrine



数据库引用编号

29 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 9 FOXP3, IDH1, IDO1, JAK1, KAT5, NOS3, PIM2, STAT1, VEGFA
Endosome membrane 1 SLC6A4
Endoplasmic reticulum membrane 1 CD4
Nucleus 8 CD274, FOXP3, JAK1, KAT5, KDR, NOS3, STAT1, VEGFA
cytosol 8 FOXP3, IDH1, IDO1, JAK1, KAT5, NOS3, STAT1, TDO2
dendrite 1 STAT1
nucleoplasm 5 CD274, FOXP3, KAT5, NOS3, STAT1
RNA polymerase II transcription regulator complex 1 STAT1
Cell membrane 7 CD274, CD4, CD47, CD8A, KDR, PDCD1, SLC6A4
Early endosome membrane 1 CD274
Multi-pass membrane protein 3 CD47, LAPTM4A, SLC6A4
Synapse 1 SLC6A4
cell junction 1 KDR
cell surface 2 CD47, VEGFA
Golgi apparatus 4 KDR, LAPTM4A, NOS3, VEGFA
Golgi membrane 1 NOS3
lysosomal membrane 1 LAPTM4A
presynaptic membrane 1 SLC6A4
Cytoplasm, cytosol 2 IDH1, IDO1
Presynapse 1 SLC6A4
endosome 2 JAK1, KDR
plasma membrane 10 CD274, CD4, CD47, CD8A, IFNLR1, JAK1, KDR, NOS3, PDCD1, SLC6A4
Membrane 6 IFNLR1, JAK1, LAPTM4A, PDCD1, SLC6A4, VEGFA
axon 2 CCK, STAT1
caveola 1 NOS3
extracellular exosome 3 CD274, CD47, IDH1
endoplasmic reticulum 2 KDR, VEGFA
extracellular space 2 CCK, VEGFA
perinuclear region of cytoplasm 3 KAT5, NOS3, STAT1
adherens junction 1 VEGFA
mitochondrion 1 IDH1
protein-containing complex 2 FOXP3, STAT1
intracellular membrane-bounded organelle 1 KAT5
Single-pass type I membrane protein 4 CD274, CD4, CD8A, IFNLR1
Secreted 2 CCK, VEGFA
extracellular region 5 CCK, CD8A, IDH1, KDR, VEGFA
cytoplasmic side of plasma membrane 1 JAK1
[Isoform 2]: Secreted 2 CD8A, KDR
anchoring junction 1 KDR
transcription regulator complex 1 KAT5
external side of plasma membrane 5 CD274, CD4, CD8A, KDR, PDCD1
Secreted, extracellular space, extracellular matrix 1 VEGFA
actin cytoskeleton 1 CD274
nucleolus 2 KAT5, STAT1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 2 CD4, KDR
postsynaptic membrane 1 SLC6A4
Cytoplasm, perinuclear region 1 KAT5
Membrane raft 3 CD4, KDR, SLC6A4
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 2 JAK1, SLC6A4
extracellular matrix 1 VEGFA
Peroxisome 1 IDH1
peroxisomal matrix 1 IDH1
secretory granule 1 VEGFA
receptor complex 2 CD8A, KDR
Cell projection, neuron projection 1 SLC6A4
neuron projection 1 SLC6A4
chromatin 3 FOXP3, KAT5, STAT1
stereocilium bundle 1 IDO1
Late endosome membrane 1 LAPTM4A
Chromosome 1 KAT5
cytoskeleton 2 JAK1, NOS3
Nucleus, nucleolus 1 KAT5
NuA4 histone acetyltransferase complex 1 KAT5
site of double-strand break 1 KAT5
Cytoplasm, cytoskeleton, spindle pole 1 KAT5
Recycling endosome membrane 1 CD274
Endomembrane system 3 JAK1, LAPTM4A, SLC6A4
sorting endosome 1 KDR
Chromosome, centromere, kinetochore 1 KAT5
specific granule membrane 1 CD47
tertiary granule membrane 1 CD47
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
plasma membrane raft 1 CD8A
ficolin-1-rich granule lumen 1 IDH1
secretory granule lumen 1 IDH1
endoplasmic reticulum lumen 1 CD4
platelet alpha granule lumen 1 VEGFA
tertiary granule lumen 1 IDH1
kinetochore 1 KAT5
endocytic vesicle membrane 1 NOS3
mitotic spindle pole 1 KAT5
clathrin-coated endocytic vesicle membrane 1 CD4
extrinsic component of cytoplasmic side of plasma membrane 1 JAK1
histone acetyltransferase complex 1 KAT5
[Isoform 1]: Cell membrane 2 CD274, CD8A
[Isoform 4]: Secreted 1 CD274
nucleosome 1 KAT5
Swr1 complex 1 KAT5
T cell receptor complex 2 CD4, CD8A
smooth muscle contractile fiber 1 IDO1
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
serotonergic synapse 1 SLC6A4
ISGF3 complex 1 STAT1
interleukin-28 receptor complex 1 IFNLR1
piccolo histone acetyltransferase complex 1 KAT5
[Isoform 2]: Endomembrane system 1 CD274


文献列表

  • Xiaowei Liang, Hongwei Gao, Jian Xiao, Shan Han, Jia He, Renyikun Yuan, Shilin Yang, Chun Yao. Abrine, an IDO1 inhibitor, suppresses the immune escape and enhances the immunotherapy of anti-PD-1 antibody in hepatocellular carcinoma. Frontiers in immunology. 2023; 14(?):1185985. doi: 10.3389/fimmu.2023.1185985. [PMID: 37334368]
  • Wenhe Zhu, Haotian Yu, Yan Wang, Ying Chang, Jiayu Wan, Na Xu, Jinglin Wang, Wensen Liu. Integration of transcriptomics, proteomics and metabolomics data to reveal the biological mechanisms of abrin injury in human lung epithelial cells. Toxicology letters. 2019 Sep; 312(?):1-10. doi: 10.1016/j.toxlet.2019.04.033. [PMID: 31054353]
  • Subrata Laskar, Omar Espino, Debasish Bandyopadhyay. Isolation, Solid-state Structure Determination, In Silico and In Vitro Anticancer Evaluation of an Indole Amino Acid Alkaloid L-Abrine. Current cancer drug targets. 2019; 19(9):707-715. doi: 10.2174/1568009619666190111111937. [PMID: 30636612]
  • Samantha L Isenberg, Melissa D Carter, Michael A Miller, Aleksandra I Noras, Mike A Mojica, Sean T Carlsen, Chinthaka P Bulathsinghala, Jerry D Thomas, Rudolph C Johnson. Quantification of Ricinine and Abrine in Human Plasma by HPLC-MS-MS: Biomarkers of Exposure to Ricin and Abrin. Journal of analytical toxicology. 2018 Nov; 42(9):630-636. doi: 10.1093/jat/bky040. [PMID: 29931062]
  • Anthony G Dodge, Kelvin Carrasquillo, Luis Rivera, Lei Xu, Lawrence P Wackett, Michael J Sadowsky. Rapid method using two microbial enzymes for detection of L-abrine in food as a marker for the toxic protein abrin. Applied and environmental microbiology. 2015 Mar; 81(5):1610-5. doi: 10.1128/aem.03492-14. [PMID: 25527549]
  • Joe Valentine Wooten, Christopher T Pittman, Thomas A Blake, Jerry D Thomas, John J Devlin, Renee A Higgerson, Rudolph C Johnson. A case of abrin toxin poisoning, confirmed via quantitation of L-abrine (N-methyl-L-tryptophan) biomarker. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2014 Dec; 10(4):392-4. doi: 10.1007/s13181-013-0377-9. [PMID: 24522983]
  • Nandita Saxena, Preeti Yadav, Om Kumar. The Fas/Fas ligand apoptotic pathway is involved in abrin-induced apoptosis. Toxicological sciences : an official journal of the Society of Toxicology. 2013 Sep; 135(1):103-18. doi: 10.1093/toxsci/kft139. [PMID: 23788630]
  • A S Bala Bhaskar, Nimesh Gupta, P V Lakshmana Rao. Transcriptomic profile of host response in mouse brain after exposure to plant toxin abrin. Toxicology. 2012 Sep; 299(1):33-43. doi: 10.1016/j.tox.2012.05.005. [PMID: 22595364]
  • Bo Zhu, Miao-Miao Lou, Guan-Lin Xie, Guo-Qing Zhang, Xue-Ping Zhou, Bin Li, Gu-Lei Jin. Horizontal gene transfer in silkworm, Bombyx mori. BMC genomics. 2011 May; 12(?):248. doi: 10.1186/1471-2164-12-248. [PMID: 21595916]
  • Henricus A M Mutsaers, Lambertus P van den Heuvel, Lauke H J Ringens, Anita C A Dankers, Frans G M Russel, Jack F M Wetzels, Joost G Hoenderop, Rosalinde Masereeuw. Uremic toxins inhibit transport by breast cancer resistance protein and multidrug resistance protein 4 at clinically relevant concentrations. PloS one. 2011 Apr; 6(4):e18438. doi: 10.1371/journal.pone.0018438. [PMID: 21483698]
  • Rudolph C Johnson, Yingtao Zhou, Ram Jain, Sharon W Lemire, Shannon Fox, Pat Sabourin, John R Barr. Quantification of L-abrine in human and rat urine: a biomarker for the toxin abrin. Journal of analytical toxicology. 2009 Mar; 33(2):77-84. doi: 10.1093/jat/33.2.77. [PMID: 19239732]
  • Janel Owens, Carolyn Koester. Quantitation of abrine, an indole alkaloid marker of the toxic glycoproteins abrin, by liquid chromatography/tandem mass spectrometry when spiked into various beverages. Journal of agricultural and food chemistry. 2008 Dec; 56(23):11139-43. doi: 10.1021/jf802471y. [PMID: 19007169]
  • Do Kyung Kim, Yoshikatsu Kanai, Hirotaka Matsuo, Ju Young Kim, Arthit Chairoungdua, Yukari Kobayashi, Atsushi Enomoto, Seok Ho Cha, Tomoyuki Goya, Hitoshi Endou. The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan; 79(1):95-103. doi: 10.1006/geno.2001.6678. [PMID: 11827462]
  • R S Zand, D J Jenkins, E P Diamandis. Steroid hormone activity of flavonoids and related compounds. Breast cancer research and treatment. 2000 Jul; 62(1):35-49. doi: 10.1023/a:1006422302173. [PMID: 10989984]
  • H DIACONO. Action of the abrine on the hemolytic complex of the guinea pig anti-sheep serum; determination of its anticomplementary power. Annales pharmaceutiques francaises. 1949 Nov; 7(11):655-9. doi: NULL. [PMID: 15404664]