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4-Hydroxyproline (FDB013511)

Record Information
Version1.0
Creation date2010-04-08 22:10:45 UTC
Update date2019-11-26 03:08:31 UTC
Primary IDFDB013511
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxyproline
Description4-Hydroxyproline, also known as 4HYP, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives 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. 4-Hydroxyproline is a very strong basic compound (based on its pKa). 4-Hydroxyproline is found, on average, in the highest concentration within a few different foods, such as sausages, hamburgers, and flaxseeds and in a lower concentration in wheats, green bell peppers, and red bell peppers. 4-Hydroxyproline has also been detected, but not quantified in, several different foods, such as other soy products, parsley, baked beans, cow milks, and lasagna. This could make 4-hydroxyproline a potential biomarker for the consumption of these foods.
CAS Number51-35-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives 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
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Foods
  • Meats
    • 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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00ku-9000000000-f5bd67093b2f30a6f62b2014-09-20View Spectrum
    GC-MS4-Hydroxyproline, 2 TMS, GC-MS Spectrumsplash10-0a4i-1900000000-e3910e1dc927e83c680dSpectrum
    GC-MS4-Hydroxyproline, 3 TMS, GC-MS Spectrumsplash10-000x-1950000000-e5d9c364cb81dbbcf7c8Spectrum
    GC-MS4-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-0a4i-1900000000-e3910e1dc927e83c680dSpectrum
    GC-MS4-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-000x-1950000000-e5d9c364cb81dbbcf7c8Spectrum
    Predicted GC-MS4-Hydroxyproline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-07g3-9100000000-7e4ece693ce885f2589cSpectrum
    Predicted GC-MS4-Hydroxyproline, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5910000000-8b634c853b803e2ce4d3Spectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-1900000000-6e39861126508ab0b88b2017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-c0b2003453a19bfc37d72015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9400000000-1e365ce40f4342e109832015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-95dfbe4457c528ad98ed2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-4328dec4e0cf083ba05d2015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-8900000000-a8cabd8deaa24da3b2192015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9000000000-1216ea21a7fab26c6cf72015-04-25View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100.7 MHz, D2O, experimental)Spectrum
    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
    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 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).