Record Information
Version1.0
Creation date2011-09-21 00:26:58 UTC
Update date2015-07-21 06:57:36 UTC
Primary IDFDB023252
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number124505-87-9
Structure
Thumb
Synonyms
SynonymSource
pentosidinehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H26N6O4
IUPAC name(2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12)C(O)=O
Average Molecular Weight378.4261
Monoisotopic Molecular Weight378.20155335
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-4094000000-b245a56b4c9094108ea2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-4211910000-59669c61174e8270f661JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-854262062e9598613fa0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-1197000000-4461d8ac18aadaf3b3dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-2690000000-9ecd9c1086a3f55eb39eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0149000000-2a909c3ad75709cde23eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pk-0293000000-eeb163c55cfb060f0c61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1950000000-5d9db7e4abc522668b22JSpectraViewer
ChemSpider ID106787
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID119593
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03933
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPentosidine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference