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

Molecular Formula	C5H9NO3
Molecular Weight	131.1299
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Separation and evaluation of the cis and trans isomers of hydroxyprolines: effect of hydrolysis on the epimerization.	1984 Feb	6731795
A criterion to determine whether cis-4-hydroxyproline is produced in animal tissues.	1984 Mar	6703705
Quantitation of hydroxyproline isomers in acid hydrolysates by high-performance liquid chromatography.	1984 May 1	6742416
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
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
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
In vivo imaging approaches in animal models of rheumatoid arthritis.	2003	12823846
Evolutionary and functional implications of the complex glycosylation of Skp1, a cytoplasmic/nuclear glycoprotein associated with polyubiquitination.	2003 Feb	12678488
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
Hydroxyproline content of needle biopsies as an objective measure of liver fibrosis: Emphasis on sampling variability.	2005 Jul	15955222
The crystal structure of the collagen-like polypeptide (glycyl-4(R)-hydroxyprolyl-4(R)-hydroxyprolyl)9 at 1.55 A resolution shows up-puckering of the proline ring in the Xaa position.	2005 May 27	15784619
Stereoelectronic and steric effects in the collagen triple helix: toward a code for strand association.	2005 Nov 16	16277536
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
Dual mechanism of zinc-proline catalyzed aldol reactions in water.	2006 Apr 14	16575434
Conformational preference and cis-trans isomerization of 4(R)-substituted proline residues.	2006 Feb 2	16471763
Stereoelectronic effects on polyproline conformation.	2006 Jan	16373476
Nutraceuticals in the management of osteoarthritis.	2007 Aug	17727018
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
Bone phenotypes in response to gonadotropin misexpression: the role for gonadotropins in postmenopausal osteoporosis.	2008 Nov 30	20428406
Stereoselective synthesis and biological evaluations of novel 3'-deoxy-4'-azaribonucleosides as inhibitors of hepatitis C virus RNA replication.	2009 Jul 9	19419173
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:10:53 UTC 2023` Edited by `admin` on `Fri Dec 15 15:10:53 UTC 2023`
Record UNII	RMB44WO89X
Record Status	`Validated (UNII)`
Record Version

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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