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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2023-02-21 17:16:10 UTC
HMDB IDHMDB0002113
Secondary Accession Numbers
  • HMDB02113
Metabolite Identification
Common Name3-Hydroxy-L-proline
Description3-Hydroxy-L-proline 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. 3-Hydroxy-L-proline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxy-L-proline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Hydroxy-L-proline.
Structure
Data?1676999770
Synonyms
ValueSource
cis-3-Hydroxy-D-prolineChEBI
Procollagen trans-3-hydroxy-L-prolineHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid
Traditional Name3-hydroxy-L-proline
CAS Registry Number4298-08-2
SMILES
O[C@H]1CCN[C@H]1C(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1
InChI KeyBJBUEDPLEOHJGE-IUYQGCFVSA-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
  • D-alpha-amino acid
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Pyrrolidine
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility431 g/LALOGPS
logP-3.2ALOGPS
logP-3.7ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)1.61ChemAxon
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
Polarizability12.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.91231661259
DarkChem[M-H]-122.84331661259
DeepCCS[M+H]+123.42230932474
DeepCCS[M-H]-119.55530932474
DeepCCS[M-2H]-156.94630932474
DeepCCS[M+Na]+132.43530932474
AllCCS[M+H]+129.032859911
AllCCS[M+H-H2O]+124.432859911
AllCCS[M+NH4]+133.432859911
AllCCS[M+Na]+134.632859911
AllCCS[M-H]-121.832859911
AllCCS[M+Na-2H]-123.832859911
AllCCS[M+HCOO]-126.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-L-prolineO[C@H]1CCN[C@H]1C(O)=O2479.0Standard polar33892256
3-Hydroxy-L-prolineO[C@H]1CCN[C@H]1C(O)=O1274.6Standard non polar33892256
3-Hydroxy-L-prolineO[C@H]1CCN[C@H]1C(O)=O1502.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-L-proline,1TMS,isomer #1C[Si](C)(C)O[C@H]1CCN[C@H]1C(=O)O1408.6Semi standard non polar33892256
3-Hydroxy-L-proline,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O1346.0Semi standard non polar33892256
3-Hydroxy-L-proline,1TMS,isomer #3C[Si](C)(C)N1CC[C@H](O)[C@@H]1C(=O)O1414.9Semi standard non polar33892256
3-Hydroxy-L-proline,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O[Si](C)(C)C1444.3Semi standard non polar33892256
3-Hydroxy-L-proline,2TMS,isomer #2C[Si](C)(C)O[C@H]1CCN([Si](C)(C)C)[C@H]1C(=O)O1466.8Semi standard non polar33892256
3-Hydroxy-L-proline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@H]1[C@@H](O)CCN1[Si](C)(C)C1421.3Semi standard non polar33892256
3-Hydroxy-L-proline,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C1503.2Semi standard non polar33892256
3-Hydroxy-L-proline,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C1566.1Standard non polar33892256
3-Hydroxy-L-proline,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C1653.9Standard polar33892256
3-Hydroxy-L-proline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CCN[C@H]1C(=O)O1671.2Semi standard non polar33892256
3-Hydroxy-L-proline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O1588.8Semi standard non polar33892256
3-Hydroxy-L-proline,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1CC[C@H](O)[C@@H]1C(=O)O1691.3Semi standard non polar33892256
3-Hydroxy-L-proline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O[Si](C)(C)C(C)(C)C1898.5Semi standard non polar33892256
3-Hydroxy-L-proline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CCN([Si](C)(C)C(C)(C)C)[C@H]1C(=O)O1939.3Semi standard non polar33892256
3-Hydroxy-L-proline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O)CCN1[Si](C)(C)C(C)(C)C1912.2Semi standard non polar33892256
3-Hydroxy-L-proline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C2181.5Semi standard non polar33892256
3-Hydroxy-L-proline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C2192.3Standard non polar33892256
3-Hydroxy-L-proline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C2076.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-b543b8f19baf933e25102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-8920000000-a1f57d10065421ae56292017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Positive-QTOFsplash10-03e9-2900000000-128ccf9715c5890c54042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Positive-QTOFsplash10-03xr-9600000000-8c3c68532a2b86bfd0282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Positive-QTOFsplash10-0fr6-9000000000-d018e434f138775d41202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Negative-QTOFsplash10-001r-7900000000-3230ec745853fb03ffc22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Negative-QTOFsplash10-02u9-9300000000-8240d8b2c6fddad070852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Negative-QTOFsplash10-0673-9000000000-a3fea27c28e95706d0ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Positive-QTOFsplash10-000i-9400000000-f8803de3984022a6de112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Positive-QTOFsplash10-00kr-9000000000-7199742da3eaa66ad5642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Positive-QTOFsplash10-00kf-9000000000-f8bbde6aa62a6d9afa3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Negative-QTOFsplash10-001i-1900000000-df968a68e6f2ab76adc22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Negative-QTOFsplash10-0006-9200000000-c73aa9b436f74ef75e9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Negative-QTOFsplash10-052f-9000000000-08bc65f1f17e8bcb3d042021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112177
KNApSAcK IDNot Available
Chemspider ID9312313
KEGG Compound IDC04397
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6494
PubChem Compound11137200
PDB IDNot Available
ChEBI ID87840
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSinha, Surajit; Tilve, Santosh; Chandrasekaran, Srinivasan. A convenient synthesis of trans-3-hydroxy-L-proline. ARKIVOC (Gainesville, FL, United States) (2005), (11), 209-217.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Basement membrane-associated chondroitin sulfate proteoglycan (CSPG). Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens, especially types IV and V. May be involved in the secretory pathway of cells. Has growth suppressive activity in fibroblasts.
Gene Name:
LEPRE1
Uniprot ID:
Q32P28
Molecular weight:
78921.41
General function:
Involved in oxidoreductase activity
Specific function:
Shows prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types II, IV and V (By similarity).
Gene Name:
LEPREL1
Uniprot ID:
Q8IVL5
Molecular weight:
60386.32
General function:
Involved in iron ion binding
Specific function:
Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types IV and V (By similarity).
Gene Name:
LEPREL2
Uniprot ID:
Q8IVL6
Molecular weight:
81835.705