Prolylhydroxyproline (CHEM022756)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:50:59 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022756
Identification
Common NameProlylhydroxyproline
ClassSmall Molecule
DescriptionA dipeptide composed of L-proline and L-hydroxyproline residues. It is a biomarker for bone collagen degradation.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
L-Pro-L-hypChEBI
L-Prolyl-L-hydroxyprolineChEBI
(4R)-L-Prolyl-4-hydroxy-L-prolineHMDB
4-Hydroxy-1-L-prolyl-prolineHMDB
L-4-Hydroxy-1-L-prolyl-prolineHMDB
Proline-hydroxyprolineHMDB
trans-4-Hydroxy-1-L-prolyl-prolineHMDB
ProlylhydroxyprolineChEBI
Pro-hydroxy-ProHMDB
Pro-HypHMDB
Proline hydroxyproline dipeptideHMDB
Proline-hydroxyproline dipeptideHMDB
Chemical FormulaC10H16N2O4
Average Molecular Mass228.245 g/mol
Monoisotopic Mass228.111 g/mol
CAS Registry Number18684-24-7
IUPAC Name(2S,4R)-4-hydroxy-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
Traditional Nameproline-hydroxyproline
SMILESO[C@@H]1C[C@H](N(C1)C(=O)[C@@H]1CCCN1)C(O)=O
InChI IdentifierInChI=1S/C10H16N2O4/c13-6-4-8(10(15)16)12(5-6)9(14)7-2-1-3-11-7/h6-8,11,13H,1-5H2,(H,15,16)/t6-,7+,8+/m1/s1
InChI KeyONPXCLZMBSJLSP-CSMHCCOUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP-4ChemAxon
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.87 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.37 m³·mol⁻¹ChemAxon
Polarizability22.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-9200000000-cefb6332c4f93d2283b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4l-2692000000-7b1c4c7371558705bfb0Spectrum
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
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9200000000-6af4dc9ae133d399503cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0b90-2900000000-84bcb537803c3e383c98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1490000000-d607eb5709327adc37c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9520000000-53efc51e1a53a9bb992eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-c54979309cb483b47143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0690000000-385af9502303330863e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05o0-3920000000-648587bfd6a99e5a6a25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0239-9200000000-e801efd4fdf93e14e8f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u1-4890000000-317a4ceb981d4c1d3a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2900000000-cb814d27ee8198848547Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-df69d58c4ec35c77f011Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-5690000000-afc10370af26972ee32dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9610000000-4039cba60bbe790e2e1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9300000000-0dd3ad4a047284fe2d79Spectrum
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
1D NMR13C 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 IDHMDB0006695
FooDB IDFDB024028
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10077215
ChEBI ID74767
PubChem Compound ID11902892
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12636053
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22382331
3. ustova, V.; Blaha, Karel. Amino acids and peptides. CXXVI. Dipeptides containing proline and 4-hydroxyproline. Collection of Czechoslovak Chemical Communications (1975), 40(3), 662-9.
4. Pohlidal A, Husek P, Palicka V, Slabik D, Hill M, Matucha P: Novel and traditional biomarkers of bone turnover in postmenopausal women. Clin Chem Lab Med. 2003 Jan;41(1):74-8.
5. Husek P, Pohlidal A, Slabik D: Rapid screening of urinary proline-hydroxyproline dipeptide in bone turnover studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 5;767(1):169-74.
6. Kodama H, Nakamura H, Sugahara K, Numajiri Y: Liquid chromatography-mass spectrometry for the qualitative analyses of iminodipeptides in the urine of patients with prolidase deficiency. J Chromatogr. 1990 May 18;527(2):279-88.
7. Sugahara K, Kodama H: Liquid chromatography-mass spectrometry for simultaneous analyses of iminodipeptides containing an N-terminal or a C-terminal proline. J Chromatogr. 1991 Apr 19;565(1-2):408-15.
8. Zhang J, Sugahara K, Yasuda K, Kodama H, Sagara Y, Kodama H: The effects of serum iminodipeptides and prednisolone on superoxide generation and tyrosyl phosphorylation of proteins in neutrophils from a patient with prolidase deficiency. Free Radic Biol Med. 1998 Mar 15;24(5):689-98.
9. Kawaguchi T, Nanbu PN, Kurokawa M: Distribution of prolylhydroxyproline and its metabolites after oral administration in rats. Biol Pharm Bull. 2012;35(3):422-7.
10. Lampiaho K, Nikkari T, Pikkarainen J, Karkkainen J, Kulonen E: Unexpected occurrence of prolylhydroxyproline during the analysis of collagen-bound carbohydrates by gas-liquid chromatography. J Chromatogr. 1972 Feb 2;64(2):211-8.
11. Bienenstock HKIBRICK AC: Urinary excretion of prolylhydroxyproline in rheumatic diseases. Ann Rheum Dis. 1969 Jan;28(1):28-30.
12. Codini M, Palmerini CA, Fini C, Lucarelli C, Floridi A: High-performance liquid chromatographic method for the determination of prolyl peptides in urine. J Chromatogr. 1991 Jan 4;536(1-2):337-41.
13. KIBRICK AC, HASHIRO CQ, SCHULTZ RS, WALTERS MI, MILHORAT AT: PROLYLHYDROXYPROLINE IN URINE: ITS DETERMINATION AND OBSERVATIONS IN MUSCULAR DYSTROPHY. Clin Chim Acta. 1964 Oct;10:344-51.
14. Hueckel HJ, Rogers QR: Prolylhydroxyproline absorption in hamsters. Can J Biochem. 1972 Jul;50(7):782-90.
15. Lowry M, Hall DE, Brosnan JT: Metabolism of glycine- and hydroxyproline-containing peptides by the isolated perfused rat kidney. Biochem J. 1985 Jul 15;229(2):545-9.
16. Kibrick AC, Power HL, Sevendal E, Milhorat AT: Prolylhydroxyproline in urine: improved method for detecting radioactivity with a scanner on full sheets of chromatography paper. Anal Biochem. 1968 Oct 24;25(1):40-5.
17. KIBRICK AC, HASHIRO CQ, WALTERS MI, MILHORAT AT: DIKETOPIPERAZINE OF PROLYLHYDROXYPROLINE IN NORMAL HUMAN URINE. Proc Soc Exp Biol Med. 1965 Jan;118:62-4.
18. Zhang A, Sun H, Han Y, Yuan Y, Wang P, Song G, Yuan X, Zhang M, Xie N, Wang X: Exploratory urinary metabolic biomarkers and pathways using UPLC-Q-TOF-HDMS coupled with pattern recognition approach. Analyst. 2012 Sep 21;137(18):4200-8. doi: 10.1039/c2an35780a. Epub 2012 Jul 31.
19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.