Record Information
Version1.0
Creation date2010-04-08 22:10:45 UTC
Update date2018-05-29 01:05:32 UTC
Primary IDFDB013511
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxyproline
DescriptionConstituent of proteins [DFC]. 4-hydroxyproline is a biomarker for the consumption of processed meat . 4-Hydroxyproline is found in many foods, some of which are parsnip, ginger, chinese cinnamon, and garlic.
CAS Number51-35-4
Structure
Thumb
Synonyms
SynonymSource
4HYpChEBI
4-Hydroxy-2-pyrrolidinecarboxylateGenerator
4-HydroxyprolineHMDB
4-Hydroxypyrrolidine-2-carboxylic acidHMDB
OxyprolineHMDB
Pyrrolidin-4-ol-2-carboxylic acidHMDB
4 HydroxyprolineMeSH
cis 4 HydroxyprolineMeSH
cis-4-HydroxyprolineMeSH
HydroxyprolineMeSH
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylateGenerator
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acidChEBI
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acidHMDB
(2S,4R)-trans-4-HydroxyprolineChEBI
(4R)-4-Hydroxy-L-prolineHMDB
4-Hydroxy-2-pyrrolidinecarboxylic acidHMDB
4-Hydroxy-L-prolinemanual
4-L-HydroxyprolineHMDB
delta-HydroxyprolineChEBI
HydroxiprolineHMDB
Hydroxy-L-prolineChEBI
Hydroxy-prolineHMDB
HyproChEBI
L-4-HydroxyprolineChEBI
L-HydroxyprolineHMDB
L-threo-4-HydroxyprolineChEBI
L-trans-4-Hydroxyprolinemanual
LS-hydroxyprolineHMDB
OxaceprolHMDB
trans-4-Hydroxy-L-prolineChEBI
trans-4-HydroxyprolineHMDB
trans-HydroxyprolineChEBI
trans-L-HydroxyprolineChEBI
δ-hydroxyprolineGenerator
Predicted Properties
PropertyValueSource
Water Solubility492 g/LALOGPS
logP-3.3ALOGPS
logP-3.7ChemAxon
logS0.57ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
pKa (Strongest Basic)10.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.38 m³·mol⁻¹ChemAxon
Polarizability12.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H9NO3
IUPAC name4-hydroxypyrrolidine-2-carboxylic acid
InChI IdentifierInChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)
InChI KeyPMMYEEVYMWASQN-UHFFFAOYSA-N
Isomeric SMILESOC1CNC(C1)C(O)=O
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
Classification
DescriptionThis compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Alpha-amino acid
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • 1,2-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 45.80%; H 6.92%; N 10.68%; O 36.60%DFC
Melting PointMp 274°DFC
Boiling PointNot Available
Experimental Water Solubility361 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logP-3.17HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.73 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -74.6DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-1900000000-e3910e1dc927e83c680dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000x-1950000000-e5d9c364cb81dbbcf7c8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1900000000-e3910e1dc927e83c680dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000x-1950000000-e5d9c364cb81dbbcf7c8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07g3-9100000000-7e4ece693ce885f2589cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-5910000000-8b634c853b803e2ce4d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-1900000000-6e39861126508ab0b88bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-c0b2003453a19bfc37d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9400000000-1e365ce40f4342e10983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-95dfbe4457c528ad98edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-4328dec4e0cf083ba05dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-8900000000-a8cabd8deaa24da3b219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9000000000-1216ea21a7fab26c6cf7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00ku-9000000000-f5bd67093b2f30a6f62bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5605
ChEMBL IDCHEMBL352418
KEGG Compound IDC01157
Pubchem Compound ID5810
Pubchem Substance IDNot Available
ChEBI ID18240
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00725
CRC / DFC (Dictionary of Food Compounds) IDKCQ80-R:JDV18-Z
EAFUS ID1781
Dr. Duke ID4-HYDROXY-PROLINE|HYDROXYPROLINE
BIGG ID36935
KNApSAcK IDNot Available
HET IDHYP
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
vulnerary73336 A drug used in treating and healing of wounds.DUKE
Enzymes
NameGene NameUniProt ID
Prolyl 4-hydroxylase subunit alpha-2P4HA2O15460
Prolyl 4-hydroxylase subunit alpha-1P4HA1P13674
Prolyl 4-hydroxylase subunit alpha-3P4HA3Q7Z4N8
Egl nine homolog 1EGLN1Q9GZT9
Egl nine homolog 2EGLN2Q96KS0
Egl nine homolog 3EGLN3Q9H6Z9
Transmembrane prolyl 4-hydroxylaseP4HTMQ9NXG6
Dipeptidyl peptidase 4DPP4P27487
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).