基本情報
- CAS
124505-87-9- 標準SMILES
N[C@@H](CCCCn1cccc2nc(NCCC[C@H](N)C(=O)O)nc1-2)C(=O)O- InChIKey
AYEKKSTZQYEZPU-RYUDHWBXSA-N- 分子式
- C17H26N6O4
- 平均分子量
- 378.4 g/mol
- 単同位体質量
- 378.20155331
概要
Pentosidine is an imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively. It has a role as a cross-linking reagent and a biomarker. It is an imidazopyridine and a non-proteinogenic L-alpha-amino acid.
名称と識別子
- 優先名称
- Pentosidine
- IUPAC
- (2S)-2-amino-6-[2-[[(4S)-4-amino-4-carboxybutyl]amino]imidazo[4,5-b]pyridin-4-yl]hexanoic acid
- 現地名
- PENTOSIDINE-D3 TFA SALT
- 英語名
- (2S)-2-amino-6-[8-[[(4S)-4-amino-4-carboxy-butyl]amino]-2,7,9-triazabicyclo[4.3.0]nona-3,5,7,9-tetraen-2-yl]hexanoic acid
- 分子式
- C17H26N6O4
- 分子量
- 378.43
名称と別名
名称をさらに表示
データベース識別子
- CAS
124505-87-9- PubChem CID
- 119593
- DTXSID
DTXSID60154417- ChEBI
CHEBI:59951- UNII
- BJ4I2X2CQJ
- Nikkaji
- J481.628E
物性
構造計算による物性
- XLogP
- -4.7
- 極性表面積
- 169 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 9
- 回転可能結合数
- 12
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 494
実験および物理化学的性質
物理化学的性質
- 沸点
- 655.6 · 655.6±65.0 °C(Predicted)
- 比重(密度)
- 1.47 · 1.47±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 21.4 mg/ml; · DMF: 21.4 mg/ml; DMSO: 22.4 mg/ml; Ethanol: 31.3 mg/ml; PBS (pH 7.2): 10 mg/ml
- 外見
- A crystalline solid
- 酸解離定数(Pka)
- 2.5 · 2.50±0.24(Predicted)
- 安定性
- Hygroscopic
安全と法規制
毒性情報
Toxicity Summary
Uremic toxins such as pentosidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
Signs and Symptoms
As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.
安全データ
- hs_code
- 2922498590
化学と産業
薬理情報
MeSH Pharmacological Classification
Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.
用途と製造
応用分野
説明Advanced glycation end products (AGEs) are compounds formed by non-enzymatic chemical reactions following the bonding of sugars to proteins or lipids during diabetes, uremia, aging, rheumatic arthritis, and other conditions. A receptor for the AGEs (RAGE) binds certain members of this class to initiate cell signaling. Pentosidine is a well-characterized natural AGE that is often used as a biomarker for the production of all AGEs. While pentosidine can be measured in urine, the majority of this AGE is catabolized before excretion.
使用A biochemical marker of bone turnover for management of metabolic bone diseases.
サプライヤー19 社
補足説明
定義ChEBI: An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively.
関連反応
化合物ノート
読み込み中…