Pentosidine

HCID 119593

Basic information

CAS
124505-87-9
Standard SMILES
N[C@@H](CCCCn1cccc2nc(NCCC[C@H](N)C(=O)O)nc1-2)C(=O)O
InChIKey
AYEKKSTZQYEZPU-RYUDHWBXSA-N
Molecular formula
C17H26N6O4
Average molar mass
378.4 g/mol
Monoisotopic mass
378.20155331

Overview

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.

Names & identifiers

Preferred name
Pentosidine
IUPAC
(2S)-2-amino-6-[2-[[(4S)-4-amino-4-carboxybutyl]amino]imidazo[4,5-b]pyridin-4-yl]hexanoic acid
English name
(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
Molecular formula
C17H26N6O4
Molecular weight
378.43

Names & synonyms

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
Show more names
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

Database identifiers

CAS
124505-87-9
PubChem CID
119593
DTXSID
DTXSID60154417
ChEBI
CHEBI:59951
UNII
BJ4I2X2CQJ
Nikkaji
J481.628E

Properties

Computed structural properties

XLogP
-4.7
Topological polar surface area
169 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
9
Rotatable bonds
12
Heavy atoms
27

Experimental & physicochemical properties

Physical DescriptionSolid

Physicochemical properties

Boiling point
655.6 · 655.6±65.0 °C(Predicted)
Density
1.47 · 1.47±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
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
form
A crystalline solid
pka
2.5 · 2.50±0.24(Predicted)

Safety & regulation

Toxicology

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 item

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 item

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).

Safety data

hs_code
2922498590
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H312-H315-H319-H332-H335
Precautionary statements
P260-P280

Chemistry & industry

Pharmacology

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 item

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.

Uses & manufacturing

UsesNaturally produced by the body (endogenous).
Applications · 2 items

DescriptionAdvanced 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.

UsesA biochemical marker of bone turnover for management of metabolic bone diseases.

Suppliers19 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]

Additional notes

DefinitionChEBI: An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively.

Related reactions

4 records

Compound notes

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