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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-30 20:56:21 UTC
Update Date2019-07-23 14:38:57 UTC
HMDB IDHMDB0240251
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-4-Hydroxyproline
Descriptioncis-4-Hydroxyproline, also known as L-allo-hydroxyproline or H-cis-hyp-OH, 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 a very strong basic compound (based on its pKa). Outside of the human body, cis-4-Hydroxyproline is found, on average, in the highest concentration within a few different foods, such as oats, ryes, and wheats and in a lower concentration in saskatoon berries, nanking cherries, and yellow bell peppers. cis-4-Hydroxyproline has also been detected, but not quantified in, green bell peppers. This could make cis-4-hydroxyproline a potential biomarker for the consumption of these foods.
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
HydroxyprolineHMDB
4 HydroxyprolineHMDB
4-HydroxyprolineHMDB
OxyprolineHMDB
cis 4 HydroxyprolineHMDB
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
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
Not Available
Physical Properties
StateNot Available
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
Polarizability12.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-54b8ac52a265772761b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9400000000-8302666cfee04dd777ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-94ec52ef1a3baca29cedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-276917674ec7e7c3d6dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-7900000000-dbe7a1905f8ee1beda93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-cec6276d54ed5d3a5424Spectrum
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01015
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440015
PDB IDHZP
ChEBI ID28397
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available