Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-30 20:56:21 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240251
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-4-Hydroxyproline
Descriptioncis 4-Hydroxyproline, also known as L-allo-hydroxyproline, 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. cis 4-Hydroxyproline is found, on average, in the highest concentration within a few different foods, such as oats (Avena sativa), ryes (Secale cereale), and wheats (Triticum) and in a lower concentration in white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.), red bell peppers (Capsicum annuum), and garden onions (Allium cepa). cis 4-Hydroxyproline has also been detected, but not quantified in, green bell peppers (Capsicum annuum). This could make cis 4-hydroxyproline a potential biomarker for the consumption of these foods. cis 4-Hydroxyproline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on cis 4-Hydroxyproline.
Structure
Data?1563892737
Synonyms
ValueSource
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylic acidChEBI
4-cis-L-HydroxyprolineChEBI
Allo-4-hydroxy-L-prolineChEBI
L-Allo-hydroxyprolineChEBI
L-cis-4-HydroxyprolineChEBI
L-AllohydroxyprolineKegg
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylateGenerator
cis-4-Hydroxy-L-prolineHMDB
cis-HydroxyprolineHMDB
(4S)-4-Hydroxy-L-prolineHMDB
(2S,4S)-4-HydroxyprolineHMDB
(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acidHMDB
(S)-allo-HydroxyprolineHMDB
4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acidHMDB
4-cis-Hydroxy-L-prolineHMDB
4-allo-HydroxyprolineHMDB
L-allo-4-HydroxyprolineHMDB
allo-4-HydroxyprolineHMDB
allo-Hydroxy-L-prolineHMDB
allo-L-HydroxyprolineHMDB
H-cis-Hyp-OHHMDB
NSC 206274HMDB
cis-4-HydroxyprolineHMDB, MeSH
HydroxyprolineMeSH, HMDB
4 HydroxyprolineMeSH, HMDB
4-HydroxyprolineMeSH, HMDB
OxyprolineMeSH, HMDB
cis 4 HydroxyprolineMeSH, HMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
Traditional NameL-hydroxyproline
CAS Registry Number618-27-9
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-/m0/s1
InChI KeyPMMYEEVYMWASQN-IMJSIDKUSA-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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available126.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00001744
[M+H]+Not Available128.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00001744
Predicted Molecular 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
Polarizability12.22 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]+127.1431661259
DarkChem[M-H]-124.66331661259
DeepCCS[M+H]+126.13530932474
DeepCCS[M-H]-123.26730932474
DeepCCS[M-2H]-160.01830932474
DeepCCS[M+Na]+135.41630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-4-HydroxyprolineO[C@@H]1CN[C@@H](C1)C(O)=O2552.8Standard polar33892256
cis-4-HydroxyprolineO[C@@H]1CN[C@@H](C1)C(O)=O1284.4Standard non polar33892256
cis-4-HydroxyprolineO[C@@H]1CN[C@@H](C1)C(O)=O1552.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-4-Hydroxyproline,1TMS,isomer #1C[Si](C)(C)O[C@@H]1CN[C@H](C(=O)O)C11449.4Semi standard non polar33892256
cis-4-Hydroxyproline,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN11354.4Semi standard non polar33892256
cis-4-Hydroxyproline,1TMS,isomer #3C[Si](C)(C)N1C[C@@H](O)C[C@H]1C(=O)O1432.0Semi standard non polar33892256
cis-4-Hydroxyproline,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN11442.1Semi standard non polar33892256
cis-4-Hydroxyproline,2TMS,isomer #2C[Si](C)(C)O[C@H]1C[C@@H](C(=O)O)N([Si](C)(C)C)C11471.9Semi standard non polar33892256
cis-4-Hydroxyproline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1[Si](C)(C)C1442.8Semi standard non polar33892256
cis-4-Hydroxyproline,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C1500.8Semi standard non polar33892256
cis-4-Hydroxyproline,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C1594.0Standard non polar33892256
cis-4-Hydroxyproline,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C1683.5Standard polar33892256
cis-4-Hydroxyproline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1CN[C@H](C(=O)O)C11682.0Semi standard non polar33892256
cis-4-Hydroxyproline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN11602.4Semi standard non polar33892256
cis-4-Hydroxyproline,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C[C@@H](O)C[C@H]1C(=O)O1698.2Semi standard non polar33892256
cis-4-Hydroxyproline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN11905.5Semi standard non polar33892256
cis-4-Hydroxyproline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)C11989.8Semi standard non polar33892256
cis-4-Hydroxyproline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1[Si](C)(C)C(C)(C)C1919.3Semi standard non polar33892256
cis-4-Hydroxyproline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C2197.5Semi standard non polar33892256
cis-4-Hydroxyproline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C2189.9Standard non polar33892256
cis-4-Hydroxyproline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C2100.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-4-Hydroxyproline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Positive-QTOFsplash10-014l-9000000000-b23d222f2dfeb06049c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Positive-QTOFsplash10-000i-9200000000-80dde78ab7695bc1272a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Positive-QTOFsplash10-00kr-9000000000-6f9557455a7abfe0faea2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Positive-QTOFsplash10-03di-3900000000-54b8ac52a265772761b52019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Positive-QTOFsplash10-02t9-9400000000-8302666cfee04dd777ff2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Positive-QTOFsplash10-014l-9000000000-94ec52ef1a3baca29ced2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Negative-QTOFsplash10-001i-2900000000-276917674ec7e7c3d6db2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Negative-QTOFsplash10-03yi-7900000000-dbe7a1905f8ee1beda932019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Negative-QTOFsplash10-00kf-9000000000-cec6276d54ed5d3a54242019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Negative-QTOFsplash10-01q9-3900000000-206002d6953f7b8754ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Negative-QTOFsplash10-03y0-9600000000-624dbd787acc76434f162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Negative-QTOFsplash10-0006-9000000000-73f483e220b16df3a0ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Positive-QTOFsplash10-03yr-4900000000-956289a1f2420b73ca3d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Positive-QTOFsplash10-014i-9100000000-b31bfff7a750b532e9182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Positive-QTOFsplash10-0aou-9000000000-9473acfa9148a036c0ba2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB030011
KNApSAcK IDC00050777
Chemspider ID389029
KEGG Compound IDC01015
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28397
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available