Record Information
Version1.0
Creation Date2016-09-30 22:35:32 UTC
Update Date2020-06-04 20:47:59 UTC
MCDB ID BMDB0000725
Secondary Accession Numbers
  • BMDB00725
Metabolite Identification
Common NameHydroxyproline
Description4-Hydroxyproline, also known as Hyp or oxaceprol, 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 drug which is used in france as a combination product for the treatment of small, superficial wounds. 4-Hydroxyproline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 4-Hydroxyproline exists in all living species, ranging from bacteria to humans. 4-Hydroxyproline is a potentially toxic compound. 4-Hydroxyproline has been found to be associated with several diseases known as ulcerative colitis, hemodialysis, crohn's disease, and alzheimer's disease; also 4-hydroxyproline has been linked to the inborn metabolic disorders including iminoglycinuria.
Structure
Thumb
Synonyms
ValueSource
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acidChEBI
(2S,4R)-trans-4-HydroxyprolineChEBI
delta-HydroxyprolineChEBI
Hydroxy-L-prolineChEBI
HydroxyprolineChEBI
HypChEBI
HyproChEBI
L-4-HydroxyprolineChEBI
L-Threo-4-hydroxyprolineChEBI
trans-HydroxyprolineChEBI
trans-L-HydroxyprolineChEBI
L-HydroxyprolineKegg
trans-4-Hydroxy-L-prolineKegg
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylateGenerator
Δ-hydroxyprolineGenerator
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acidHMDB
(4R)-4-Hydroxy-L-prolineHMDB
4-Hydroxy-2-pyrrolidinecarboxylic acidHMDB
4-Hydroxy-L-prolineHMDB
4-L-HydroxyprolineHMDB
HydroxiprolineHMDB
Hydroxy-prolineHMDB
LS-HydroxyprolineHMDB
OxaceprolHMDB
trans-4-HydroxyprolineHMDB
4 HydroxyprolineHMDB
OxyprolineHMDB
(-)-4-Hydroxy-2-pyrrolidinecarboxylic acidHMDB
(2S,4R)-(-)-4-HydroxyprolineHMDB
(2S,4R)-4-HydroxyprolineHMDB
(R)-4-Hydroxy-(S)-prolineHMDB
(R)-4-Hydroxy-L-prolineHMDB
(S)-HydroxyprolineHMDB
4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic acidHMDB
4(R)-HydroxyprolineHMDB
4-Hydroxy-(S)-prolineHMDB
4-trans-Hydroxy-L-prolineHMDB
L-HyproHMDB
L-trans-4-HydroxyprolineHMDB
NSC 46704HMDB
trans-L-4-HydroxyprolineHMDB
4-HydroxyprolineHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
Traditional Namehypro
CAS Registry Number51-35-4
SMILES
O[C@H]1CN[C@@H](C1)C(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
InChI KeyPMMYEEVYMWASQN-DMTCNVIQSA-N
Chemical Taxonomy
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
  • L-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability12.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000x-0950000000-5b1c397e26b28e872d202014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000x-0950000000-c46b5bba0f41001e3c182014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9530000000-00db00b15ab5341d7d642014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001l-1960000000-abcd0377696d2b52d8152014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0590000000-75e03328fb2d444690572017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000x-0950000000-c46b5bba0f41001e3c182017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9530000000-00db00b15ab5341d7d642017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001l-1960000000-abcd0377696d2b52d8152017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000x-0940000000-97328204c6b60a2446162017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000x-0940000000-468aeb79950a9e6dadc62017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-40c0bfa9451caacaf4222017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9100000000-af92b4a861832ca4ec132016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02mu-9670000000-81c8390bdfa262fa9b2f2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-9700000000-ea3ed008938a57d1263c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014r-9000000000-0b76109525f362b600a02012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-477e41e40831316e68ac2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0019-9300000000-7228a10f32d447b58ee02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-11800ca52c6e911f83132012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-11800ca52c6e911f83132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-1900000000-b6bba00a324b6eab209f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-1900000000-ba9df49a4d967cf8851d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-6d125b0bb59101e9ce532017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0019-9300000000-7228a10f32d447b58ee02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-9600000000-5bcced64c9dfeb96876f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-9600000000-b575fa8df5e2d8bb3a992017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-c036fd15ccf6ed0c554e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-8746de5249187bab94dc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-3f70e8e1eef8568e87ef2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-cd32fa744ef013f5ca482021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-3ea6a86203c48888d5282021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-02tc-9000000000-95aa07d1970d7f83f3472021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-9000000000-95b2178b5433b4b2db502021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-a10576d40ff1d7fc707a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9400000000-8b66308781907cdf63042016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-7f9d42864b2decdbdd1d2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-bfc9154f784caa2e61a72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ar-9800000000-750b3fd4f0e1dcb8ef4c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9000000000-efe39f47f6ee937ded3d2016-09-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00ku-9000000000-f5bd67093b2f30a6f62b2018-05-25View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified5.1 +/- 0.1 uM details
Detected and Quantified4.6 +/- 0.1 uM details
Detected and Quantified4.9 +/- 0.1 uM details
Detected and Quantified5.1 +/- 0.1 uM details
HMDB IDHMDB0000725
DrugBank IDDB08847
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013511
KNApSAcK IDC00001370
Chemspider ID5605
KEGG Compound IDC01157
BioCyc ID4-HYDROXY-L-PROLINE
BiGG ID36935
Wikipedia LinkHydroxyproline
METLIN ID257
PubChem Compound5810
PDB IDNot Available
ChEBI ID18095
References
Synthesis ReferenceAdams, Elijah; Goldstone, Alfred. Hydroxyproline metabolism. II. Enzymic preparation and properties of D1-pyrroline-3-hydroxy-5-carboxylic acid. Journal of Biological Chemistry (1960), 235 3492-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals (2009). Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics.
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.