HYDROXYPROLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H9NO3
Molecular Weight	131.1299
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1CN[C@@H](C1)C(O)=O

InChI

InChIKey=PMMYEEVYMWASQN-DMTCNVIQSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0000725 | https://www.ncbi.nlm.nih.gov/mesh/68006909

HYDROXYPROLINE, a hydroxylated form of the imino acid proline, is a major component of the protein collagen. For this reason, HYDROXYPROLINE content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. A deficiency in ascorbic acid can result in impaired HYDROXYPROLINE formation.

Approval Year

PubMed

Title	Date	PubMed
Studies on bound trans-4-hydroxy-L-proline in sandal (Santalum album L.).	1970 Oct	5493503
Urinary excretion of hydroxyproline, hydroxylysine and hydroxylysine glycosides by patients with Paget's disease of bone and carcinoma with metastases in bone.	1979 Mar 15	436278
A criterion to determine whether cis-4-hydroxyproline is produced in animal tissues.	1984 Mar	6703705
Hydroxyproline and total protein levels in gingiva and gingival crevicular fluid in periodontally healthy human subjects.	1992 Sep	1287145
Hydroxyproline and total protein levels in gingiva and gingival crevicular fluid in patients with juvenile, rapidly progressive, and adult periodontitis.	1993 May	8515361
Elevated serum aminoterminal procollagen type-III-peptide parallels collagen accumulation in rats with secondary biliary fibrosis.	1996 Jul	8836905
Hydroxyproline and total protein levels in gingiva from patients treated with phenytoin and cyclosporine-A.	1996 Mar	8648408
Preventive and therapeutic effects in rats of hepatocyte growth factor infusion on liver fibrosis/cirrhosis.	1997 Jul	9214455
Measurement of histidinohydroxylysinonorleucine and hydroxyproline in skin collagen by reversed-phase high-performance liquid chromatography after 9-fluorenylmethyl chloroformate labeling.	1997 Oct 15	9344411
Basic principles and clinical applications of biochemical markers of bone metabolism: biochemical and technical aspects.	1999 Fall	10548826
Norplant((R)) implants and progesterone vaginal rings do not affect maternal bone turnover and density during lactation and after weaning.	1999 Oct	10527977
Enzymatic production of trans-4-hydroxy-L-proline by regio- and stereospecific hydroxylation of L-proline.	2000 Apr	10830487
Preparation of functionalized, conformationally constrained DTPA analogues from L- or D-serine and trans-4-hydroxy-L-proline. Hydroxymethyl substituents on the central acetic acid and on the backbone.	2000 Jun 30	10866623
The importance of the N-terminal beta-turn in bradykinin antagonists.	2000 Oct	11089646
The synthesis of 4-arylsulfanyl-substituted kainoid analogues from trans-4-hydroxy-L-proline.	2000 Sep 4	10987419
Oxaceprol, an atypical inhibitor of inflammation, reduces leukocyte adherence in mouse antigen-induced arthritis.	2001 Jun	11480608
Pharmacologic pain treatment of musculoskeletal disorders: current perspectives and future prospects.	2001 Mar	11289086
Biochemical measurements in the prediction of histologic subtype of renal transplant bone disease in women.	2002 Aug	12148113
[Meta-analysis of the efficacy of adenosylmethionine and oxaceprol in the treatment of osteoarthritis].	2002 Nov	12436324
Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance.	2002 Sep	12297216
Substituted 2-azabicyclo[2.1.1]hexanes as constrained proline analogues: implications for collagen stability.	2004 Dec 10	15575731
O-acylation of hydroxyproline residues: effect on peptide-bond isomerization and collagen stability.	2005	15558658
Effects of dietary conjugated linoleic acid on production and metabolic parameters in transition dairy cows grazing fresh pasture.	2006 Aug	16836800
Oxaceprol--a randomised, placebo-controlled clinical study in osteoarthritis with a non-conventional non-steroidal anti-inflammatory drug.	2007 Jan-Feb	17417987
Comparison of plasma malondialdehyde, glutathione, glutathione peroxidase, hydroxyproline and selenium levels in patients with vitiligo and healthy controls.	2008	19882005
Extracellular matrix and HIF-1 signaling: the role of prolidase.	2008 Mar 15	17999410
4-chloroprolines: synthesis, conformational analysis, and effect on the collagen triple helix.	2008 May	17937398
Conformational preferences of substrates for human prolyl 4-hydroxylase.	2008 Sep 9	18702512
Origin of the stability conferred upon collagen by fluorination.	2009 Jul 15	19423349
Stereoselective synthesis and biological evaluations of novel 3'-deoxy-4'-azaribonucleosides as inhibitors of hepatitis C virus RNA replication.	2009 Jul 9	19419173
Direct and continuous assay for prolyl 4-hydroxylase.	2009 Mar 15	19111518
Quantum mechanical and NMR studies of ring puckering and cis/trans-rotameric interconversion in prolines and hydroxyprolines.	2009 Oct 8	19757781
The aberrance of the 4S diastereomer of 4-hydroxyproline.	2010 Aug 11	20681719
Prolidase-dependent regulation of TGF β (corrected) and TGF β receptor expressions in human skin fibroblasts.	2010 Dec 15	20868675
Immunostimulatory activities of Bacillus simplex DR-834 to carp (Cyprinus carpio).	2010 Sep	20472068

Patents

Name

Type

Language

HYDROXYPROLINE

Official Name

English

L-PROLINE, 4-HYDROXY-, (4R)-

Systematic Name

English

HYDROXYPROLINE [INCI]

Common Name

English

NSC-46704

Code

English

4-HYDROXY-L-PROLINE

Systematic Name

English

HYDROXYPROLINE [MI]

Common Name

English

Hydroxyproline [WHO-DD]

Common Name

English

(2S,4R)-4-HYDROXYPROLINE

Systematic Name

English

HYP

Common Name

English

L-HYDROXYPROLINE

Systematic Name

English

4-HYDROXYPROLINE

Systematic Name

English

LUMISTOR

Brand Name

English

L-PROLINE, 4-HYDROXY-, TRANS-

Systematic Name

English

Classification Tree Code System Code

LOINC

27181-7