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
Prolidase-dependent regulation of TGF β (corrected) and TGF β receptor expressions in human skin fibroblasts.	2010-12-15	20868675
Immunostimulatory activities of Bacillus simplex DR-834 to carp (Cyprinus carpio).	2010-09	20472068
The aberrance of the 4S diastereomer of 4-hydroxyproline.	2010-08-11	20681719
Essential modification of the Sircol Collagen Assay for the accurate quantification of collagen content in complex protein solutions.	2010-08	20144751
Thermodynamic consequences of incorporating 4-substituted proline derivatives into a small helical protein.	2010-05-18	20405858
Prolyl 4-hydroxylase.	2010-04	20199358
Quantum mechanical and NMR studies of ring puckering and cis/trans-rotameric interconversion in prolines and hydroxyprolines.	2009-10-08	19757781
Origin of the stability conferred upon collagen by fluorination.	2009-07-15	19423349
Stereoselective synthesis and biological evaluations of novel 3'-deoxy-4'-azaribonucleosides as inhibitors of hepatitis C virus RNA replication.	2009-07-09	19419173
Direct and continuous assay for prolyl 4-hydroxylase.	2009-03-15	19111518
Bone phenotypes in response to gonadotropin misexpression: the role for gonadotropins in postmenopausal osteoporosis.	2008-11-30	20428406
Conformational preferences of substrates for human prolyl 4-hydroxylase.	2008-09-09	18702512
4-chloroprolines: synthesis, conformational analysis, and effect on the collagen triple helix.	2008-05	17937398
Extracellular matrix and HIF-1 signaling: the role of prolidase.	2008-03-15	17999410
Comparison of plasma malondialdehyde, glutathione, glutathione peroxidase, hydroxyproline and selenium levels in patients with vitiligo and healthy controls.	2008	19882005
Effects of glycosylation of (2S,4R)-4-hydroxyproline on the conformation, kinetics, and thermodynamics of prolyl amide isomerization.	2007-09-26	17764180
Nutraceuticals in the management of osteoarthritis.	2007-08	17727018
p53 activation by knockdown technologies.	2007-05-25	17530925
Oxaceprol--a randomised, placebo-controlled clinical study in osteoarthritis with a non-conventional non-steroidal anti-inflammatory drug.	2007-04-10	17417987
Effects of dietary conjugated linoleic acid on production and metabolic parameters in transition dairy cows grazing fresh pasture.	2006-08	16836800
2005 Emil Thomas Kaiser Award.	2006-05	16641494
Dual mechanism of zinc-proline catalyzed aldol reactions in water.	2006-04-14	16575434
Conformational preference and cis-trans isomerization of 4(R)-substituted proline residues.	2006-02-02	16471763
Stereoelectronic effects on polyproline conformation.	2006-01	16373476
Stereoelectronic and steric effects in the collagen triple helix: toward a code for strand association.	2005-11-16	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.	2005-10	15980055
Hydroxyproline content of needle biopsies as an objective measure of liver fibrosis: Emphasis on sampling variability.	2005-07	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.	2005-05-27	15784619
Adenosine postsynaptically modulates supraoptic neuronal excitability.	2005-01	15356187
O-acylation of hydroxyproline residues: effect on peptide-bond isomerization and collagen stability.	2005	15558658
Substituted 2-azabicyclo[2.1.1]hexanes as constrained proline analogues: implications for collagen stability.	2004-12-10	15575731
Prescription of drugs to pregnant women in France: the HIMAGE study.	2004-04-03	15058494
Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1.	2004-04	14718599
Evolutionary and functional implications of the complex glycosylation of Skp1, a cytoplasmic/nuclear glycoprotein associated with polyubiquitination.	2003-02	12678488
In vivo imaging approaches in animal models of rheumatoid arthritis.	2003	12823846
[Meta-analysis of the efficacy of adenosylmethionine and oxaceprol in the treatment of osteoarthritis].	2002-11	12436324
Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance.	2002-09	12297216
Biochemical measurements in the prediction of histologic subtype of renal transplant bone disease in women.	2002-08	12148113
Oxaceprol, an atypical inhibitor of inflammation, reduces leukocyte adherence in mouse antigen-induced arthritis.	2001-06	11480608
Measurement of histidinohydroxylysinonorleucine and hydroxyproline in skin collagen by reversed-phase high-performance liquid chromatography after 9-fluorenylmethyl chloroformate labeling.	1997-10-15	9344411
Preventive and therapeutic effects in rats of hepatocyte growth factor infusion on liver fibrosis/cirrhosis.	1997-07	9214455
Elevated serum aminoterminal procollagen type-III-peptide parallels collagen accumulation in rats with secondary biliary fibrosis.	1996-07	8836905
Hydroxyproline and total protein levels in gingiva from patients treated with phenytoin and cyclosporine-A.	1996-03	8648408
Hydroxyproline and total protein levels in gingiva and gingival crevicular fluid in patients with juvenile, rapidly progressive, and adult periodontitis.	1993-05	8515361
Hydroxyproline and total protein levels in gingiva and gingival crevicular fluid in periodontally healthy human subjects.	1992-09	1287145
Quantitation of hydroxyproline isomers in acid hydrolysates by high-performance liquid chromatography.	1984-05-01	6742416
A criterion to determine whether cis-4-hydroxyproline is produced in animal tissues.	1984-03	6703705
Separation and evaluation of the cis and trans isomers of hydroxyprolines: effect of hydrolysis on the epimerization.	1984-02	6731795
Urinary excretion of hydroxyproline, hydroxylysine and hydroxylysine glycosides by patients with Paget's disease of bone and carcinoma with metastases in bone.	1979-03-15	436278
Studies on bound trans-4-hydroxy-L-proline in sandal (Santalum album L.).	1970-10	5493503

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:13 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:13 GMT 2025`
Record UNII	RMB44WO89X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-46704

Preferred Name

English

HYDROXYPROLINE

Official Name

English

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

Systematic Name

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