Pyridinoline (CHEM021853)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:02 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021853
Identification
Common NamePyridinoline
ClassSmall Molecule
DescriptionPyridinoline is a breakdown product of bone collagen. It can be used as a bone marker to measure osteoclastic activity.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-PyridinolineHMDB
1-(2S)-(+)-PyridinolineHMDB
4-((2S)-2-Amino-2-carboxyethyl)-1-((2R,5S)-5-amino-5-carboxy-2-hydroxypentyl)-3-((3S)-3-amino-3-carboxypropyl)-5-hydroxy-pyridinium inner saltHMDB
HydroxylysylpyridinolineHMDB
Hydroxylysyl pyridinolineHMDB
PyridinolineMeSH
Chemical FormulaC18H28N4O8
Average Molecular Mass428.437 g/mol
Monoisotopic Mass428.191 g/mol
CAS Registry Number63800-01-1
IUPAC Name4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(2R,5S)-5-amino-5-carboxylato-2-hydroxypentyl]-5-hydroxypyridin-1-ium
Traditional Name4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(2R,5S)-5-amino-5-carboxylato-2-hydroxypentyl]-5-hydroxypyridin-1-ium
SMILESN[C@@H](CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C18H28N4O8/c19-12(16(25)26)3-1-9-6-22(7-10(23)2-4-13(20)17(27)28)8-15(24)11(9)5-14(21)18(29)30/h6,8,10,12-14,23H,1-5,7,19-21H2,(H3-,24,25,26,27,28,29,30)/t10-,12+,13+,14+/m1/s1
InChI KeyLCYXYLLJXMAEMT-SAXRGWBVSA-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
  • Tricarboxylic acid or derivatives
  • Hydroxypyridine
  • Aralkylamine
  • Pyridine
  • Pyridinium
  • Heteroaromatic compound
  • Carboxylic acid salt
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP-3.9ALOGPS
logP-13ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)0.73ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area237.13 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity114.84 m³·mol⁻¹ChemAxon
Polarizability43.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1139100000-5d8fc20ccc7b98532363Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001u-3200292000-91125c23cde5753b8015Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_47) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_47) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Pyridinoline,4TMS,#47" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0001900000-1071214d48bc921584a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-0009400000-b7f8b4454b46b9b588a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054t-1429200000-e0435f18dbbf7dca10c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-843d31dfa041aff3e01eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1100900000-c38c200cd8e6b732fd69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7921000000-79aa7de87908b35ae0f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-0049600000-efbf48db5b13ec3bbc8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m1-0079100000-8c7b3a51061cf35c058dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-5191000000-2ca942a932b82f93dd7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0arr-1046900000-0dcaf90573f090897648Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0feb-6795000000-c3f12a8a1fc8ebb5c46eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7593000000-56e695190149fe7749c2Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000851
FooDB IDFDB010805
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5814
PDB IDNot Available
Wikipedia LinkPyridinoline
Chemspider ID94798
ChEBI ID88539
PubChem Compound ID105068
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Allevi, Pietro; Cribiu, Riccardo; Giannini, Elios; Anastasia, Mario. Practical syntheses of pyridinolines, important amino acidic biomarkers of collagen health. Journal of Organic Chemistry (2007), 72(9), 3478-3483.
2. Fujimoto D, Moriguchi T: Pyridinoline, a non-reducible crosslink of collagen. Quantitative determination, distribution, and isolation of a crosslinked peptide. J Biochem. 1978 Mar;83(3):863-7.
3. Ricard-Blum S, Esterre P, Grimaud JA: Collagen cross-linking by pyridinoline occurs in non-reversible skin fibrosis. Cell Mol Biol (Noisy-le-grand). 1993 Nov;39(7):723-7.
4. Ueda M, Inaba M, Okuno S, Maeno Y, Ishimura E, Yamakawa T, Nishizawa Y: Serum BAP as the clinically useful marker for predicting BMD reduction in diabetic hemodialysis patients with low PTH. Life Sci. 2005 Jul 22;77(10):1130-9.
5. Okamura T, Akita H, Tatsura H, Kawai N, Nagata D, Azemoto M, Iwase Y, Kohri K: The efficacy of a serum carboxyterminal pyridinoline cross-linked telopeptide of type I collagen as a quantitative screening marker for bone metastases in patients with urological malignancies. Cancer Detect Prev. 2003;27(1):14-8.
6. Bank RA, Verzijl N, Lafeber FP, Tekoppele JM: Putative role of lysyl hydroxylation and pyridinoline cross-linking during adolescence in the occurrence of osteoarthritis at old age. Osteoarthritis Cartilage. 2002 Feb;10(2):127-34.
7. van der Slot AJ, van Dura EA, de Wit EC, De Groot J, Huizinga TW, Bank RA, Zuurmond AM: Elevated formation of pyridinoline cross-links by profibrotic cytokines is associated with enhanced lysyl hydroxylase 2b levels. Biochim Biophys Acta. 2005 Jun 30;1741(1-2):95-102. Epub 2004 Oct 5.
8. Istok R, Bely M, Stancikova M, Rovensky J: Evidence for increased pyridinoline concentration in fibrotic tissues in diffuse systemic sclerosis. Clin Exp Dermatol. 2001 Sep;26(6):545-7.
9. Teichmann J, Lange U, Stracke H, Federlin K, Bretzel RG: Bone metabolism and bone mineral density of systemic lupus erythematosus at the time of diagnosis. Rheumatol Int. 1999;18(4):137-40.
10. Vesper HW, Audain C, Woolfitt A, Ospina M, Barr J, Robins SP, Myers GL: High-performance liquid chromatography method to analyze free and total urinary pyridinoline and deoxypyridinoline. Anal Biochem. 2003 Jul 15;318(2):204-11.
11. Wan KC, Wu HT, Chan HP, Hung LK: Effects of antioxidants on pyridinoline cross-link formation in culture supernatants of fibroblasts from normal skin and hypertrophic scars. Clin Exp Dermatol. 2002 Sep;27(6):507-12.
12. Ricard-Blum S, Bresson-Hadni S, Grenard P, Humbert P, Carbillet JP, Risteli L, Vuitton DA: The level of the collagen cross-link pyridinoline reflects the improvement of cutaneous lesions in one case of skin alveolar echinococcosis. Parasitol Res. 1998 Sep;84(9):715-9.
13. Wan KC, Chow TC: Age-related changes in the concentration of pyridinoline cross-links in human skin. Ann Clin Biochem. 1999 Sep;36 ( Pt 5):666-8.
14. Muller A, Stein G, Lehmann G, Hein G: Investigations of bone turnover in renal osteopathy. Eur J Med Res. 1999 Feb 25;4(2):78-84.
15. Miyamoto KK, McSherry SA, Robins SP, Besterman JM, Mohler JL: Collagen cross-link metabolites in urine as markers of bone metastases in prostatic carcinoma. J Urol. 1994 Apr;151(4):909-13.
16. Takahashi M, Kushida K, Ohishi T, Kawana K, Hoshino H, Uchiyama A, Inoue T: Quantitative analysis of crosslinks pyridinoline and pentosidine in articular cartilage of patients with bone and joint disorders. Arthritis Rheum. 1994 May;37(5):724-8.
17. Tilson MD, Davis G: Deficiencies of copper and a compound with ion-exchange characteristics of pyridinoline in skin from patients with abdominal aortic aneurysms. Surgery. 1983 Aug;94(2):134-41.
18. Fernandes RJ, Eyre DR: The elastin-like protein matrix of lamprey branchial cartilage is cross-linked by lysyl pyridinoline. Biochem Biophys Res Commun. 1999 Aug 11;261(3):635-40.