PENTOSIDINE-D3 TFA SALT

Pentosidine

HCID 119593

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

Pentosidine124505-87-9BJ4I2X2CQJCHEBI:59951DTXSID601544176-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)-L-norleucine(2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid4H-Imidazo(4,5-b)pyridine-4-hexanoic acid, alpha-amino-2-((4-amino-4-carboxybutyl)amino)-, (S-(R*,R*))-6-(2-(((4S)-4-Amino-4-carboxybutyl)amino)-4H-imidazo(4,5-b)pyridin-4-yl)-L-norleucine(2S)-2-amino-6-(2-(((4S)-4-amino-4-carboxybutyl)amino)-4H-imidazo(4,5-b)pyridin-4-yl)hexanoic acidRefChem:171499DTXCID6076908
名称をさらに表示
PENTOSIDINE-D3 TFA SALTペントシジン(2S)-2-アミノ-6-(2-{[(4S)-4-アミノ-4-カルボキシブチル]アミノ}-4H-イミダゾ[4,5-b]ピリジン-4-イル)ヘキサン酸(αS)-α-アミノ-2-[[(S)-4-アミノ-4-カルボキシブチル]アミノ]-4H-イミダゾ[4,5-b]ピリジン-4-ヘキサン酸Pentosidine. TFA saltGefitinib Impurity 109PENTOSIDINE 2,2,2-TRIFLUOROACETATE4H-Imidazo[4,5-b]pyridine-4-hexanoic acid, α-amino-2-[[(4S)-4-amino-4-carboxybutyl]amino]-, (αS)-(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 acid2-((S)-4-ACETAMIDO-4-CARBOXYBUTYLAMINO)-4-((S)-5-ACETAMIDO-5-CARBOXYPENTYL)-3H-IMIDAZO[4,5-B]PYRIDIN-4-IUM 2,2,2-TRIFLUOROACETATE
MFCD11111968(2S)-2-amino-6-[2-[[(4S)-4-amino-4-carboxybutyl]amino]imidazo[4,5-b]pyridin-4-yl]hexanoic acidC17H26N6O4(S)-2-Amino-6-(2-(((S)-4-amino-4-carboxybutyl)amino)-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acidUNII-BJ4I2X2CQJ4H-Imidazo(4,5-b)pyridine-4-hexanoic acid, alpha-amino-2-(((4S)-4-amino-4-carboxybutyl)amino)-, (alphaS)-4H-Imidazo[4,5-b]pyridine-4-hexanoic acid, alpha-amino-2-[[(4S)-4-amino-4-carboxybutyl]amino]-, (alphaS)-Epitope ID:140093

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

実験および物理化学的性質

Physical DescriptionSolid

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)

安全と法規制

毒性情報

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 件

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 · 1 件

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

hs_code
2922498590

化学と産業

薬理情報

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
MeSH Pharmacological Classification · 1 件

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

UsesNaturally produced by the body (endogenous).
応用分野 · 2 件

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

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
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MedBio脉铂医药021-69568360 18916172912 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]

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

4 件

化合物ノート

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