Record Information
Version1.0
Creation date2011-09-21 00:38:44 UTC
Update date2015-07-21 06:57:58 UTC
Primary IDFDB024028
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProlylhydroxyproline
DescriptionProlylhydroxyproline is a dipeptide. Prolylhydroxyproline is a marker of bone collagen degradation, showing high sensitivity for the diagnosis of osteoporosis. Prolylhydroxyproline has been suggested as a possible alternative to hydroxyproline determination in bone resorption studies. Prolylhydroxyproline is one of the iminodipeptides present in the urine of patients with prolidase deficiency. Prolidase (X-Pro dipeptidase EC 3.4. 13.9) splits iminodipeptides containing C-terminal proline or hydroxyproline (X-Pro or X-Hyp) to X+Pro or X+Hyp. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis and mental retardation. These patients excrete large amounts of iminodipeptides containing C-terminal proline in the urine due to hereditary prolidase deficiency. (PMID: 12636053, 11863289, 2387877, 1874885, 9586797) [HMDB]
CAS Number18684-24-7
Structure
Thumb
Synonyms
SynonymSource
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
Pro-hydroxy-proHMDB
Pro-hypHMDB
Proline hydroxyproline dipeptideHMDB
Proline-hydroxyproline dipeptideHMDB
ProlylhydroxyprolineChEBI
(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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16N2O4
IUPAC name(2S,4R)-4-hydroxy-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
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
Isomeric SMILESO[C@@H]1C[C@H](N(C1)C(=O)[C@@H]1CCCN1)C(O)=O
Average Molecular Weight228.245
Monoisotopic Molecular Weight228.11100701
Classification
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
Ontology
Disposition

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, Positivesplash10-00dj-9200000000-cefb6332c4f93d2283b3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4l-2692000000-7b1c4c7371558705bfb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1490000000-d607eb5709327adc37c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9520000000-53efc51e1a53a9bb992eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-c54979309cb483b47143JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0690000000-385af9502303330863e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05o0-3920000000-648587bfd6a99e5a6a25JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0239-9200000000-e801efd4fdf93e14e8f2JSpectraViewer
ChemSpider ID10077215
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11902892
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06695
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 IDNot Available
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