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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 07:27:23 UTC
Update Date2019-01-11 19:17:48 UTC
HMDB IDHMDB0003933
Secondary Accession Numbers
  • HMDB03933
Metabolite Identification
Common NamePentosidine
DescriptionPentosidine is a carbohydrate-derived advanced glycation end products (AGEs) that is considerably elevated in uremic patients. Derived from ribose, a pentose, pentosidine forms fluorescent cross-links between the arginine and lysine residues in collagen. It is formed in a reaction of the amino acids with the Maillard reaction products of ribose. Although it is present only in trace concentrations among tissue proteins, it is useful for assessing cumulative damage to proteins-advanced glycation endproductsThis compound per se has no biological activities but is highly correlated to the levels of precursors of carbonyl compounds, and for this reason is considered a reliable surrogate marker for AGEs. The modification of proteins in uremia is not limited to AGEs, since advanced lipoxidation end products are also demonstrable in plasma proteins in uremia. The accumulation of these compounds does not seem to be dependent only on the decline of renal function. Carbonyl precursors of AGEs and advanced lipoxidation end products are markedly elevated in uremic patients. Preliminary cross-sectional studies in haemodialysis patients seem to indicate that the AGEs and carbonyl stress may be involved in the pathogenesis of alterations in left ventricular geometry and function in these patients. (PMID 11051031 ). The plasma pentosidine level in diabetic nephropathy was found to be determined by factors such as renal function control of glucose and the patient's age; of these, renal function was the most critical factor. The pathological role of AGEs in diabetic nephropathy, is in the expanded mesangial area of diffuse diabetic glomerulosclerosis, with nodular lesions, characteristic of diabetic nephropathy. These suggests a potential link of AGEs accumulation, which may be determined by renal function, control of glucose and age, to renal tissue damage in diabetic nephropathy. (PMID 9044316 ). The rate of accumulation of glycoxidation products is accelerated in diabetes and age-adjusted concentrations of two advanced glycation end-products (AGE) in tissue proteins, N(6)-carboxymethyllysine and pentosidine, correlate with the severity of complication in diabetic patients. (PMID 9044306 ).
Structure
Data?1547234268
SynonymsNot Available
Chemical FormulaC17H26N6O4
Average Molecular Weight378.4261
Monoisotopic Molecular Weight378.20155335
IUPAC Name(2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid
Traditional Namepentosidine
CAS Registry Number124505-87-9
SMILES
N[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12)C(O)=O
InChI Identifier
InChI=1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1
InChI KeyAYEKKSTZQYEZPU-RYUDHWBXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Imidazopyridine
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Pyridine
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP-3.7ALOGPS
logP-3.9ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area169.38 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.61 m³·mol⁻¹ChemAxon
Polarizability40.55 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-4094000000-b245a56b4c9094108ea2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-4211910000-59669c61174e8270f661JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-854262062e9598613fa0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-1197000000-4461d8ac18aadaf3b3dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-2690000000-9ecd9c1086a3f55eb39eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0149000000-2a909c3ad75709cde23eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pk-0293000000-eeb163c55cfb060f0c61JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1950000000-5d9db7e4abc522668b22JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.14 +/- 0.05 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11.17 (9.89-12.45) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.53 +/- 0.79 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified0.0051 +/- 0.0016 uMAdult (>18 years old)BothRenal transplantation details
Cerebrospinal Fluid (CSF)Detected and Quantified12.5 (12.0-13.0) uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified22.5 (21.0-24.0) uMAdult (>18 years old)Not SpecifiedVascular dementia details
Associated Disorders and Diseases
Disease References
Kidney transplantation
  1. Yoshida K, Yoneda T, Fujimoto K, Hirao Y, Konishi N: Pentosidine and its deposition in renal tissue in renal transplantation. Transplant Proc. 2005 Dec;37(10):4266-72. [PubMed:16387094 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Alzheimer's disease
  1. Bar KJ, Franke S, Wenda B, Muller S, Kientsch-Engel R, Stein G, Sauer H: Pentosidine and N(epsilon)-(carboxymethyl)-lysine in Alzheimer's disease and vascular dementia. Neurobiol Aging. 2003 Mar-Apr;24(2):333-8. [PubMed:12498967 ]
Multi-infarct dementia
  1. Bar KJ, Franke S, Wenda B, Muller S, Kientsch-Engel R, Stein G, Sauer H: Pentosidine and N(epsilon)-(carboxymethyl)-lysine in Alzheimer's disease and vascular dementia. Neurobiol Aging. 2003 Mar-Apr;24(2):333-8. [PubMed:12498967 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023252
KNApSAcK IDNot Available
Chemspider ID106787
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentosidine
METLIN IDNot Available
PubChem Compound119593
PDB IDNot Available
ChEBI ID59951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bar KJ, Franke S, Wenda B, Muller S, Kientsch-Engel R, Stein G, Sauer H: Pentosidine and N(epsilon)-(carboxymethyl)-lysine in Alzheimer's disease and vascular dementia. Neurobiol Aging. 2003 Mar-Apr;24(2):333-8. [PubMed:12498967 ]
  2. Zoccali C, Mallamaci F, Tripepi G: AGEs and carbonyl stress: potential pathogenetic factors of long-term uraemic complications. Nephrol Dial Transplant. 2000;15 Suppl 2:7-11. [PubMed:11051031 ]
  3. Sugiyama S, Miyata T, Horie K, Iida Y, Tsuyuki M, Tanaka H, Maeda K: Advanced glycation end-products in diabetic nephropathy. Nephrol Dial Transplant. 1996;11 Suppl 5:91-4. [PubMed:9044316 ]
  4. Wells-Knecht KJ, Brinkmann E, Wells-Knecht MC, Litchfield JE, Ahmed MU, Reddy S, Zyzak DV, Thorpe SR, Baynes JW: New biomarkers of Maillard reaction damage to proteins. Nephrol Dial Transplant. 1996;11 Suppl 5:41-7. [PubMed:9044306 ]