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Showing Compound cis 4-Hydroxyproline (FDB030011)

Record Information
Version1.0
Creation date2015-02-26 20:21:15 UTC
Update date2019-11-26 03:21:35 UTC
Primary IDFDB030011
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis 4-Hydroxyproline
DescriptionCis 4-hydroxyproline, also known as L-allo-hydroxyproline or (2s,4s)-4-hydroxy-2-pyrrolidinecarboxylic acid, belongs to proline and derivatives class of compounds. Those 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 soluble (in water) and a moderately acidic compound (based on its pKa). Cis 4-hydroxyproline can be found in a number of food items such as green bell pepper, wheat, nanking cherry, and oat, which makes cis 4-hydroxyproline a potential biomarker for the consumption of these food products.
CAS Number618-27-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
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
Polarizability12.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H9NO3
IUPAC name(2S,4S)-4-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)/t3-,4-/m0/s1
InChI KeyPMMYEEVYMWASQN-IMJSIDKUSA-N
Isomeric SMILESO[C@@H]1CN[C@@H](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
  • 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScis 4-Hydroxyproline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-b23d222f2dfeb06049c32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-80dde78ab7695bc1272a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-6f9557455a7abfe0faea2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-54b8ac52a265772761b52019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9400000000-8302666cfee04dd777ff2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-94ec52ef1a3baca29ced2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-276917674ec7e7c3d6db2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-7900000000-dbe7a1905f8ee1beda932019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-cec6276d54ed5d3a54242019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-3900000000-206002d6953f7b8754ab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03y0-9600000000-624dbd787acc76434f162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-73f483e220b16df3a0ab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03yr-4900000000-956289a1f2420b73ca3d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-b31bfff7a750b532e9182021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-9473acfa9148a036c0ba2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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 IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference