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
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
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
[Meta-analysis of the efficacy of adenosylmethionine and oxaceprol in the treatment of osteoarthritis].	2002 Nov	12436324
In vivo imaging approaches in animal models of rheumatoid arthritis.	2003	12823846
Prescription of drugs to pregnant women in France: the HIMAGE study.	2003 Nov-Dec	15058494
Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1.	2004 Apr	14718599
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
Adenosine postsynaptically modulates supraoptic neuronal excitability.	2005 Jan	15356187
Cross-talk between farnesoid-X-receptor (FXR) and peroxisome proliferator-activated receptor gamma contributes to the antifibrotic activity of FXR ligands in rodent models of liver cirrhosis.	2005 Oct	15980055
Effects of dietary conjugated linoleic acid on production and metabolic parameters in transition dairy cows grazing fresh pasture.	2006 Aug	16836800
Stereoelectronic effects on polyproline conformation.	2006 Jan	16373476
Nutraceuticals in the management of osteoarthritis.	2007 Aug	17727018
Effects of glycosylation of (2S,4R)-4-hydroxyproline on the conformation, kinetics, and thermodynamics of prolyl amide isomerization.	2007 Sep 26	17764180
Comparison of plasma malondialdehyde, glutathione, glutathione peroxidase, hydroxyproline and selenium levels in patients with vitiligo and healthy controls.	2008	19882005
4-chloroprolines: synthesis, conformational analysis, and effect on the collagen triple helix.	2008 May	17937398
Bone phenotypes in response to gonadotropin misexpression: the role for gonadotropins in postmenopausal osteoporosis.	2008 Nov 30	20428406
Conformational preferences of substrates for human prolyl 4-hydroxylase.	2008 Sep 9	18702512
Stereoselective synthesis and biological evaluations of novel 3'-deoxy-4'-azaribonucleosides as inhibitors of hepatitis C virus RNA replication.	2009 Jul 9	19419173
Prolyl 4-hydroxylase.	2010 Apr	20199358
The aberrance of the 4S diastereomer of 4-hydroxyproline.	2010 Aug 11	20681719
Thermodynamic consequences of incorporating 4-substituted proline derivatives into a small helical protein.	2010 May 18	20405858

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