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Record Information
Version1.0
Creation Date2016-09-30 22:35:32 UTC
Update Date2020-06-04 20:47:59 UTC
BMDB IDBMDB0000725
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
Biospecimen Locations
  • Blood
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified23.4 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified25 +/- 5 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified51 +/- 13 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Longissimus Thoracis MuscleDetected and Quantified32 +/- 11 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected and Quantified5.1 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.9 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5.1 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified2 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Semimembranosus MuscleDetected and Quantified31 +/- 11 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified43 +/- 12 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14.8 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy negative
details
BloodDetected and Quantified19.3 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy positive
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
HMDB IDHMDB0000725
DrugBank IDDB08847
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
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.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
DDO
Uniprot ID:
P31228
Molecular weight:
37660.0
Reactions
Hydroxyproline + Water + Oxygen → 1-Pyrroline-4-hydroxy-2-carboxylate + Ammonia + Hydrogen peroxidedetails
General function:
Involved in iron ion binding
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA1
Uniprot ID:
Q1RMU3
Molecular weight:
61010.0
General function:
Involved in iron ion binding
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA3
Uniprot ID:
Q75UG4
Molecular weight:
61023.0
Reactions
L-Proline + Oxoglutaric acid + Oxygen → Hydroxyproline + Succinic acid + Carbon dioxidedetails
General function:
Amino acid transport and metabolism
Specific function:
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by binding at least ADA, CAV1, IGF2R, and PTPRC. Its binding to CAV1 and CARD11 induces T-cell proliferation and NF-kappa-B activation in a T-cell receptor/CD3-dependent manner. Its interaction with ADA also regulates lymphocyte-epithelial cell adhesion. In association with FAP is involved in the pericellular proteolysis of the extracellular matrix (ECM), the migration and invasion of endothelial cells into the ECM. May be involved in the promotion of lymphatic endothelial cells adhesion, migration and tube formation. When overexpressed, enhanced cell proliferation, a process inhibited by GPC3. Acts also as a serine exopeptidase with a dipeptidyl peptidase activity that regulates various physiological processes by cleaving peptides in the circulation, including many chemokines, mitogenic growth factors, neuropeptides and peptide hormones. Removes N-terminal dipeptides sequentially from polypeptides having unsubstituted N-termini provided that the penultimate residue is proline.
Gene Name:
DPP4
Uniprot ID:
P81425
Molecular weight:
88369.0
General function:
Amino acid transport and metabolism
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. In some cell types, such as erythrocytes, its primary function may be the generation of NADP(+). Can utilize both NAD and NADP. Has higher affinity for NADP, but higher catalytic efficiency with NADH (By similarity). Involved in cellular response to oxidative stress (By similarity).
Gene Name:
PYCR2
Uniprot ID:
Q17QJ7
Molecular weight:
33630.0
Reactions
Hydroxyproline + NAD → Pyrroline hydroxycarboxylic acid + NADHdetails
General function:
Not Available
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:
PRODH
Uniprot ID:
Q148G5
Molecular weight:
67080.0
Reactions
Hydroxyproline → Pyrroline hydroxycarboxylic aciddetails