4467 4-Hydroxyproline 4-Hydroxyproline (or hydroxyproline or Hyp) is a major component of the protein collagen. Hydroxyproline is produced by hydroxylation of the amino acid proline and is, therefore, a post-translationally modified amino acid. Hydroxyproline and proline play key roles for collagen stability. In particular, they permit the sharp twisting of the collagen helix. Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin. For this reason, hydroxyproline content has been used as an indicator to determine collagen and/or gelatin amount in tissue or biological samples. Increased serum and urine levels of hydroxyproline have been found in Paget's disease Hydroxyproline (Hyp) content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. Bedridden and elderly individuals show significantly elevated serum levels of hydroxyproline in comparison to normal, active individuals Elevated levels of urinary hydroxyproline are also indicative of muscle damage Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (A3486, A3487, A3488, A3489). 51-35-4 5810 C5H9NO3 131.13 White powder. 274 - 275°C 361 mg/mL at 25°C No indication of carcinogenicity to humans (not listed by IARC). This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. 2014-08-29T06:51:06Z 2026-05-14T19:00:06Z Hydroxyproline C01157 18095 L-4-HYDROXY-PROLINE DB08847 HYP true O[C@H]1CN[C@@H](C1)C(O)=O C5H9NO3 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 PMMYEEVYMWASQN-DMTCNVIQSA-N 131.1299 131.058243159 Endogenous Solid -3.17 HMDB00725 CHEMBL352418 5605 <p>Adams, 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.</p> CHEM003373 DTXSID60861573 NS00013764 (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid 69.56 29.3822 12.291927113198778 1 4 3 1.6413819507648508 10.617096890348789 0 1 -3.31 0.57 4.92e+02 g/l