2-Amino-3-phosphonopropionic acid (BioDeep_00000003351)
Secondary id: BioDeep_00001868652
human metabolite Endogenous Marine Natural Products
代谢物信息卡片
化学式: C3H8NO5P (169.014)
中文名称: DL-2-氨基-3-膦酸丙酸(AP3)
谱图信息:
最多检出来源 Homo sapiens(lipidsearch) 17.49%
分子结构信息
SMILES: C(C(C(=O)O)N)P(=O)(O)O
InChI: InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
描述信息
2-Amino-3-phosphonopropionic acid (AP-3 or 2-AP3), also known as 3-phosphonoalanine, is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It is found in many organisms ranging from microbes to invertebrates to animals. In humans AP-3 is found in diverse tissues, such as liver, intestine and spleen. (PMID: 2627760). 2-Amino-3-phosphonopropionic acid is a ubiquitous naturally occurring phosphonate used as a source of phosphorus by many prokaryotic organisms (PMID: 30119975). The natural occurrence of 2-amino-3-phosphonopropionic acid. the phosphonate analogue of aspartic acid, was first reported by Kittredge & Hughes (PMID: 14214094) in the sea anemone Zoanthus sociatus and the protozoon Tetrahymena pyriformis. It has since been established to be one of the most widely distributed of the biogenic C–P compounds, particularly among the lower marine invertebrates (PMID: 19191873). AP-3 has been determined to be a metabotropic glutamate receptor agonist (PMID: 8836635). It has been shown to block the amyloid precursor protein (APP) release evoked by glutamate receptor stimulation in neurons of the cortex and hippocampus. APP accumulation is believed to produce the damage in Alzheimer’s disease (PMID: 7644542).
2-Amino-3-phosphonopropionic acid (AP-3)is a normal human metabolite found in diverse tissues, such as liver, intestine and spleen. (PMID 2627760) AP-3 is a metabotropic glutamate receptor agonist (PMID 8836635) shown to block the amyloid precursor protein (APP) release evoked by glutamate receptor stimulation in neurons of the cortex and hippocampus; APP accumulation is believed to produce the damage in Alzheimer disease (PMID 7644542) [HMDB]
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists
KEIO_ID A131
DL-AP3 is a competitive mGluR1 and mGluR5 antagonist. DL-AP3 is also an inhibitor of phosphoserine phosphatase. DL-AP3 has neuroprotective effect[1][2][3].
同义名列表
27 个代谢物同义名
2-Amino-3-phosphonopropionic acid, sodium salt; 2-Amino-3-phosphonopropionic acid, (DL)-isomer; 1-Amino-3-(phosphohydroxy)propan-2-one; DL-2-Amino-3-phosphonopropionic acid; 2-Azanyl-3-phosphono-propanoic acid; 2-Amino-3-phosphono-propionic acid; 2-Amino-3-phosphono-propanoic acid; 2-Amino-3-phosphonopropionic acid; 2-Amino-3-phosphonopropanoic acid; 1-Amino-propan-2-one-3-phosphate; 2-Amino-3-phosphopropionic acid; 2-Azanyl-3-phosphono-propanoate; 2-Amino-3-phosphono-propionate; 2-Amino-3-phosphono-propanoate; 2-Amino-3-phosphonopropionate; 2-Amino-3-phosphonopropanoate; 3-Amino-2-oxopropyl phosphate; 2-Amino-3-phosphopropionate; 3-Phosphono-L-alanine; 2-Amino-3-phosprop; 3-phosphonoalanine; D-Alanyl-phosphate; Phosphonoalanine; glyphosate; DL-AP3; L-AP3; 2-AP3
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:28388
- KEGG: C05672
- PubChem: 3857
- HMDB: HMDB0000370
- Metlin: METLIN5359
- ChEMBL: CHEMBL88621
- foodb: FDB021989
- chemspider: 3723
- CAS: 20263-06-3
- CAS: 5652-28-8
- MoNA: KO000200
- MoNA: KO002300
- MoNA: KO002298
- MoNA: KO002301
- MoNA: KO000204
- MoNA: KO002299
- MoNA: KO000203
- MoNA: KO002302
- MoNA: KO000202
- MoNA: KO000201
- PMhub: MS000009532
- PubChem: 7979
- 3DMET: B05092
- NIKKAJI: J81.069J
- medchemexpress: HY-100786
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 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(1)
- Vitamin B6:
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid ⟶ O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
PharmGKB(0)
1 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。
文献列表
- Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Chase M Kayrouz, Yeying Zhang, Tiffany M Pham, Kou-San Ju. Genome Mining Reveals the Phosphonoalamide Natural Products and a New Route in Phosphonic Acid Biosynthesis.
ACS chemical biology.
2020 07; 15(7):1921-1929. doi:
10.1021/acschembio.0c00256. [PMID: 32484327] - Frederic D Müller, Sebastian Beck, Eckhard Strauch, Michael W Linscheid. Bacterial predators possess unique membrane lipid structures.
Lipids.
2011 Dec; 46(12):1129-40. doi:
10.1007/s11745-011-3614-5. [PMID: 21984111] - M R Young, S M Fleetwood-Walker, T Dickinson, G Blackburn-Munro, H Sparrow, P J Birch, C Bountra. Behavioural and electrophysiological evidence supporting a role for group I metabotropic glutamate receptors in the mediation of nociceptive inputs to the rat spinal cord.
Brain research.
1997 Nov; 777(1-2):161-9. doi:
. [PMID: 9449425] - E Fleischer-Lambropoulos, T Kazazoglou, T Geladopoulos, S Kentroti, C Stefanis, A Vernadakis. Stimulation of glutamine synthetase activity by excitatory amino acids in astrocyte cultures derived from aged mouse cerebral hemispheres may be associated with non-N-methyl-D-aspartate receptor activation.
International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience.
1996 Jul; 14(4):523-30. doi:
10.1016/0736-5748(95)00098-4. [PMID: 8884386] - R K Lee, R J Wurtman, A J Cox, R M Nitsch. Amyloid precursor protein processing is stimulated by metabotropic glutamate receptors.
Proceedings of the National Academy of Sciences of the United States of America.
1995 Aug; 92(17):8083-7. doi:
10.1073/pnas.92.17.8083. [PMID: 7644542] - R M Manev, M Favaron, N Gabellini, P Candeo, H Manev. Functional evidence for a L-AP3-sensitive metabotropic receptor different from glutamate metabotropic receptor mGluR1.
Neuroscience letters.
1993 May; 155(1):73-6. doi:
10.1016/0304-3940(93)90676-c. [PMID: 8361667] - S A Tan, L G Tan. Distribution of ciliatine (2-aminoethylphosphonic acid) and phosphonoalanine (2-amino-3-phosphonopropionic acid) in human tissues.
Clinical physiology and biochemistry.
1989; 7(6):303-9. doi:
. [PMID: 2627760]
