MiMeDB: Showing metabocard for 4-Hydroxyproline (MMDBc0000770)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:34 UTC

Update Date

2024-10-09 16:58:54 UTC

Metabolite ID

MMDBc0000770

Metabolite Identification

Common Name

4-Hydroxyproline

Description

4-Hydroxyproline (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, non-essential amino acid. Hydroxyproline and proline play key roles in 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 (PMID: 436278 ). 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 (PMID: 10706420 ). Elevated levels of urinary hydroxyproline are also indicative of muscle damage (PMID: 21988268 ). Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (PMID: 21483218 ). 4-Hydroxyproline is found to be associated with Alzheimer's disease, and also hydroxyprolinemia and iminoglycinuria which are both inborn errors of metabolism. 4-Hydroxyproline is also involved in metabolic disorders such as hyperprolinemia type I, hyperornithinemia with gyrate atrophy (HOGA), L-arginine:glycine amidinotransferase deficiency, creatine deficiency, and guanidinoacetate methyltransferase deficiency. A deficiency in ascorbic acid can result in impaired hydroxyproline formation (PubChem). trans-4-Hydroxy-L-proline is a biomarker for the consumption of processed meat.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acid	ChEBI
(2S,4R)-trans-4-Hydroxyproline	ChEBI
delta-Hydroxyproline	ChEBI
Hydroxy-L-proline	ChEBI
Hydroxyproline	ChEBI
Hyp	ChEBI
Hypro	ChEBI
L-4-Hydroxyproline	ChEBI
L-Threo-4-hydroxyproline	ChEBI
trans-Hydroxyproline	ChEBI
trans-L-Hydroxyproline	ChEBI
L-Hydroxyproline	Kegg
trans-4-Hydroxy-L-proline	Kegg
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylate	Generator
Δ-hydroxyproline	Generator
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid	HMDB
(4R)-4-Hydroxy-L-proline	HMDB
4-Hydroxy-2-pyrrolidinecarboxylic acid	HMDB
4-Hydroxy-L-proline	HMDB
4-L-Hydroxyproline	HMDB
Hydroxiproline	HMDB
Hydroxy-proline	HMDB
LS-Hydroxyproline	HMDB
Oxaceprol	HMDB
trans-4-Hydroxyproline	HMDB
4 Hydroxyproline	HMDB
Oxyproline	HMDB
(-)-4-Hydroxy-2-pyrrolidinecarboxylic acid	HMDB
(2S,4R)-(-)-4-Hydroxyproline	HMDB
(2S,4R)-4-Hydroxyproline	HMDB
(R)-4-Hydroxy-(S)-proline	HMDB
(R)-4-Hydroxy-L-proline	HMDB
(S)-Hydroxyproline	HMDB
4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic acid	HMDB
4(R)-Hydroxyproline	HMDB
4-Hydroxy-(S)-proline	HMDB
4-trans-Hydroxy-L-proline	HMDB
L-Hypro	HMDB
L-trans-4-Hydroxyproline	HMDB
NSC 46704	HMDB
trans-L-4-Hydroxyproline	HMDB
4-Hydroxyproline	HMDB

Molecular Formula

C₅H₉NO₃

Average Mass

131.1299

Monoisotopic Mass

131.058243159

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

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

InChI Key

PMMYEEVYMWASQN-DMTCNVIQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
L-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
1,2-aminoalcohol
Amino acid
Secondary alcohol
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Amine
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

4-hydroxyproline (CHEBI:18095 )
Other amino acids (C01157 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Endoplasmic reticulum
Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Kidney
Liver
Pancreas
Placenta
Platelet
Prostate
Saliva
Skeletal Muscle
Spleen
Urine

Tissue Locations

Epidermis
Fibroblasts
Kidney
Liver
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191877	D-amino-acid oxidase	Unknown	P14920	Homo sapiens
MMDBp0191972	Prolyl 4-hydroxylase subunit alpha-2	Enzyme	O15460	Homo sapiens
MMDBp0191973	Pyrroline-5-carboxylate reductase 1, mitochondrial	Unknown	P32322	Homo sapiens
MMDBp0191974	Prolyl 4-hydroxylase subunit alpha-1	Enzyme	P13674	Homo sapiens
MMDBp0191975	Pyrroline-5-carboxylate reductase 2	Unknown	Q96C36	Homo sapiens
MMDBp0193185	Dipeptidyl peptidase 4	Enzyme	P27487	Homo sapiens
MMDBp0193396	Proline dehydrogenase 1, mitochondrial	Unknown	O43272	Homo sapiens
MMDBp0193751	Pyrroline-5-carboxylate reductase 3	Unknown	Q53H96	Homo sapiens
MMDBp0193821	Neutral amino acid transporter A	Unknown	P43007	Homo sapiens
MMDBp0194851	Transient receptor potential cation channel subfamily M member 1	Unknown	Q7Z4N2	Homo sapiens
MMDBp0195859	Prolyl 4-hydroxylase subunit alpha-3	Enzyme	Q7Z4N8	Homo sapiens
MMDBp0195916	Egl nine homolog 1	Enzyme	Q9GZT9	Homo sapiens
MMDBp0195917	Egl nine homolog 2	Enzyme	Q96KS0	Homo sapiens
MMDBp0195918	Egl nine homolog 3	Enzyme	Q9H6Z9	Homo sapiens
MMDBp0195919	Transmembrane prolyl 4-hydroxylase	Enzyme	Q9NXG6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001998	Oxoglutaric acid	4-Hydroxyproline	prolyl 4-hydroxylase, alpha polypeptide I	VMH	12714038 2543975 3034602
MMDBr0002623	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	pyrroline-5-carboxylate reductase 1	VMH	12514185 3768405 6250440 675382
MMDBr0002624	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	pyrroline-5-carboxylate reductase 1	VMH	12514185 3768405 6250440 675382
MMDBr0002625	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	pyrroline-5-carboxylate reductase 1	VMH	12514185 3768405 6250440 675382
MMDBr0002626	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	pyrroline-5-carboxylate reductase 1	VMH	12514185 3768405 6250440 675382
MMDBr0007212	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	VMH	30371894
MMDBr0008333	Oxoglutaric acid	4-Hydroxyproline	Not Available	VMH	30371894
MMDBr0008342	4-Hydroxyproline	cis-4-Hydroxy-D-proline	Not Available	VMH	30371894
MMDBr0008356	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	VMH	30371894
MMDBr0008357	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	VMH	30371894
MMDBr0010306	Oxoglutaric acid	4-Hydroxyproline	prolyl 4-hydroxylase, alpha polypeptide I	VMH; KEGG	30371894
MMDBr0010307	Oxoglutaric acid	4-Hydroxyproline	prolyl 4-hydroxylase, alpha polypeptide I	VMH; KEGG	30371894
MMDBr0010308	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	VMH	30371894
MMDBr0010309	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	VMH	30371894
MMDBr0010989	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	VMH	30371894
MMDBr0012681	4-Hydroxyproline	L-D-1-Pyrroline-5-carboxylic acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Urine	HMDB	17031479
Alzheimer's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	17031479
Alzheimer's disease	Decreased	Association	Human Blood	HMDB	17031479
Hydroxyprolinemia	Increased	Association	Human Blood	HMDB	15723447
Hydroxyprolinemia	Increased	Association	Human Urine	HMDB	15617190
Hydroxyprolinemia	Increased	Association	Human Urine	HMDB	15723447
Hydroxyprolinemia	Increased	Association	Human Blood	HMDB	15617190
Iminoglycinuria		Association	Human Urine	HMDB	19033659
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Iminoglycinuria		Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	2	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	127	Human stool; Human ; Human feces; Human saliva; Human urine; Human sputum; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque; Human mucosa; Goat feces; Sheep feces; Human vaginal secretion	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	183	Human ; Human mucosa; Human stool; Human supragingival plaque; Human feces; Human saliva; Human subgingival plaque; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human feces; pleural fluid plaque; bal; Sheep	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	59	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	46	Human feces; Human ; Human stool; Human urine	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.21	0.017			umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.28	0.055			uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Blood	Detected and Quantified	5.6	0.67			uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Blood	Detected and Quantified	5.66	0.67			uM	Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Blood	Detected and Quantified	27.0	14.1			uM	Adult (>18 years old)	Both	Hemodialysis	HMDB	10838467
Human Blood	Detected and Quantified	43.8	12.5			uM	Adult (>18 years old)	Both	Hemodialysis	HMDB	10838467
Human Blood	Detected and Quantified	339				uM	Infant (0-1 year old)	Male	Hydroxyprolinemia	HMDB	15723447
Human Urine	Detected and Quantified	1957				umol/mmol creatinine	Infant (0-1 year old)	Female	Hydroxyprolinemia	HMDB	15617190
Human Urine	Detected and Quantified	2960				umol/mmol creatinine	Infant (0-1 year old)	Male	Hydroxyprolinemia	HMDB	15723447
Human Blood	Detected and Quantified	412000				uM	Infant (0-1 year old)	Female	Hydroxyprolinemia	HMDB	15617190
Human Urine	Detected and Quantified			0	250	umol/mmol creatinine	Children (1-13 years old)	Both	Iminoglycinuria	HMDB	19033659
Human Urine	Detected and Quantified			40	150	umol/mmol creatinine	Adult (>18 years old)	Female	Iminoglycinuria	HMDB	19033659
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19033659
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19033659
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	19033659
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	19033659
Human Urine	Detected and Quantified	0.15				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected and Quantified	2				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21388201
Human Urine	Detected and Quantified	< 2.0				umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	HMDB	3168222
Human Saliva	Detected and Quantified	<0.25				uM	Adult (>18 years old)	Male	Normal	HMDB	21164041
Human Saliva	Detected and Quantified	<0.25				uM	Adult (>18 years old)	Male	Normal	HMDB	21164041
Human Urine	Detected and Quantified	<10.0				umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	HMDB	3168222
Human Urine	Detected and Quantified	<143				umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	15617190
Human Blood	Detected and Quantified	<91000				uM	Infant (0-1 year old)	Female	Normal	HMDB	15617190
Human Urine	Detected and Quantified			0	143	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	15723447
Human Urine	Detected and Quantified			0.26	0.45	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.26	0.64	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Saliva	Detected and Quantified	1.1	2.0			uM	Adult (>18 years old)	Male	Normal	HMDB	21164041
Human Urine	Detected and Quantified	1.37	0.78			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15992788
Human Saliva	Detected and Quantified	1.5	2.6			uM	Adult (>18 years old)	Male	Normal	HMDB	21164041
Human Feces	Detected and Quantified	10	10			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	13.0		3.0	23.0	uM	Adult (>18 years old)	Both	Normal	HMDB	12297216
Human Blood	Detected and Quantified			16	53	uM	Infant (0-1 year old)	Male	Normal	HMDB	15723447
Human Urine	Detected and Quantified	28.41		16.96	78.82	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	34.65		8.07	96.55	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified			4	230	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	30830347
Human Urine	Detected and Quantified	497.46	203.51			umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	19468821
Human Urine	Detected and Quantified	6.5		2.4	12.5	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	7.5	2.9			umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	3168222
Human Urine	Detected and Quantified	720.19	373.10			umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	19468821
Human Urine	Detected and Quantified	723.58	260.04			umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	19468821
Human Urine	Detected and Quantified			8.12	92.19	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	88.17	49.59			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	30.862	12.249			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	75		50	100	umol/mmol creatinine	Children (1-13 years old)	Both	Iminoglycinuria	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	11.8		9.9	13.7	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	16.0	9.0			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	186.45		145.78	227.11	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	20	12			uM	Children (1 - 13 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	20.0	11.0			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	20.0	12.0			uM	Children (1-13 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	24	13			uM	Children (1 - 13 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	24.0	13.0			uM	Children (1-13 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	40.0		28.0	55.0	uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	40.0	40.0			uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.432	0.431			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.873	0.537			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.93	0.91			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			4.00	30.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Urine	Detected and Quantified	<1.70				umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<10.067				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<2.15				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<2.49				umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<286.82				umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<5.20				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	12097436
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000725

DrugBank ID

DB08847

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18095

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kelleher PC: Urinary excretion of hydroxyproline, hydroxylysine and hydroxylysine glycosides by patients with Paget's disease of bone and carcinoma with metastases in bone. Clin Chim Acta. 1979 Mar 15;92(3):373-9. doi: 10.1016/0009-8981(79)90216-x. [PubMed:436278 ]
Akalin FA, Sengun D, Renda N, Eratalay K, Caglayan G: Hydroxyproline and total protein levels in gingiva and gingival crevicular fluid in periodontally healthy human subjects. J Nihon Univ Sch Dent. 1992 Sep;34(3):172-7. doi: 10.2334/josnusd1959.34.172. [PubMed:1287145 ]
Kuttan R, Radhakrishnan AN: Studies on bound trans-4-hydroxy-L-proline in sandal (Santalum album L.). Biochem J. 1970 Oct;119(4):651-7. doi: 10.1042/bj1190651. [PubMed:5493503 ]
Lafranconi WM, Duhamel RC, Brendel K, Huxtable RJ: Differentiation of the cardiac and pulmonary toxicity of monocrotaline, a pyrrolizidine alkaloid. Biochem Pharmacol. 1984 Jan 15;33(2):191-7. doi: 10.1016/0006-2952(84)90475-1. [PubMed:6200114 ]
Turpeenniemi-Hujanen T, Myllyla R: Concomitant hydroxylation of proline and lysine residues in collagen using purified enzymes in vitro. Biochim Biophys Acta. 1984 Jul 16;800(1):59-65. doi: 10.1016/0304-4165(84)90094-1. [PubMed:6331520 ]
Bienkowski RS: A criterion to determine whether cis-4-hydroxyproline is produced in animal tissues. Arch Biochem Biophys. 1984 Mar;229(2):455-8. doi: 10.1016/0003-9861(84)90175-9. [PubMed:6703705 ]
Last JA, Reiser KM, Tyler WS, Rucker RB: Long-term consequences of exposure to ozone. I. Lung collagen content. Toxicol Appl Pharmacol. 1984 Jan;72(1):111-8. doi: 10.1016/0041-008x(84)90254-0. [PubMed:6710477 ]
Bellon G, Berg R, Chastang F, Malgras A, Borel JP: Separation and evaluation of the cis and trans isomers of hydroxyprolines: effect of hydrolysis on the epimerization. Anal Biochem. 1984 Feb;137(1):151-5. doi: 10.1016/0003-2697(84)90362-2. [PubMed:6731795 ]
Lindblad WJ, Diegelmann RF: Quantitation of hydroxyproline isomers in acid hydrolysates by high-performance liquid chromatography. Anal Biochem. 1984 May 1;138(2):390-5. doi: 10.1016/0003-2697(84)90827-3. [PubMed:6742416 ]
Akalin FA, Sengun D, Eratalay K, Renda N, Caglayan G: Hydroxyproline and total protein levels in gingiva and gingival crevicular fluid in patients with juvenile, rapidly progressive, and adult periodontitis. J Periodontol. 1993 May;64(5):323-9. doi: 10.1902/jop.1993.64.5.323. [PubMed:8515361 ]
Akalin FA, Bozkurt FY, Sengun D, Renda N, Kalfa Z, Eratalay K, Velidedeoglu E: Hydroxyproline and total protein levels in gingiva from patients treated with phenytoin and cyclosporine-A. J Nihon Univ Sch Dent. 1996 Mar;38(1):21-30. doi: 10.2334/josnusd1959.38.21. [PubMed:8648408 ]
Gerling B, Becker M, Waldschmidt J, Rehmann M, Schuppan D: Elevated serum aminoterminal procollagen type-III-peptide parallels collagen accumulation in rats with secondary biliary fibrosis. J Hepatol. 1996 Jul;25(1):79-84. doi: 10.1016/s0168-8278(96)80331-x. [PubMed:8836905 ]
Matsuda Y, Matsumoto K, Yamada A, Ichida T, Asakura H, Komoriya Y, Nishiyama E, Nakamura T: Preventive and therapeutic effects in rats of hepatocyte growth factor infusion on liver fibrosis/cirrhosis. Hepatology. 1997 Jul;26(1):81-9. doi: 10.1053/jhep.1997.v26.pm0009214455. [PubMed:9214455 ]
Kondo A, Ishikawa O, Okada K, Miyachi Y, Abe S, Kuboki Y: Measurement of histidinohydroxylysinonorleucine and hydroxyproline in skin collagen by reversed-phase high-performance liquid chromatography after 9-fluorenylmethyl chloroformate labeling. Anal Biochem. 1997 Oct 15;252(2):255-9. doi: 10.1006/abio.1997.2322. [PubMed:9344411 ]
Diaz S, Reyes MV, Zepeda A, Gonzalez GB, Lopez JM, Campino C, Croxatto HB: Norplant((R)) implants and progesterone vaginal rings do not affect maternal bone turnover and density during lactation and after weaning. Hum Reprod. 1999 Oct;14(10):2499-505. doi: 10.1093/humrep/14.10.2499. [PubMed:10527977 ]
Seibel MJ, Woitge HW: Basic principles and clinical applications of biochemical markers of bone metabolism: biochemical and technical aspects. J Clin Densitom. 1999 Fall;2(3):299-321. doi: 10.1385/jcd:2:3:299. [PubMed:10548826 ]
Tasanen K, Eble JA, Aumailley M, Schumann H, Baetge J, Tu H, Bruckner P, Bruckner-Tuderman L: Collagen XVII is destabilized by a glycine substitution mutation in the cell adhesion domain Col15. J Biol Chem. 2000 Feb 4;275(5):3093-9. doi: 10.1074/jbc.275.5.3093. [PubMed:10652291 ]
Sodian R, Hoerstrup SP, Sperling JS, Martin DP, Daebritz S, Mayer JE Jr, Vacanti JP: Evaluation of biodegradable, three-dimensional matrices for tissue engineering of heart valves. ASAIO J. 2000 Jan-Feb;46(1):107-10. doi: 10.1097/00002480-200001000-00025. [PubMed:10667727 ]
Koike K, Li Y, Seo M, Sakurada I, Tezuka K, Uchikura K: Free 4-hydroxyproline content in serum of bedridden aged people is elevated due to fracture. Biol Pharm Bull. 2000 Jan;23(1):101-3. doi: 10.1248/bpb.23.101. [PubMed:10706420 ]
Dixon IM, Hao J, Reid NL, Roth JC: Effect of chronic AT(1) receptor blockade on cardiac Smad overexpression in hereditary cardiomyopathic hamsters. Cardiovasc Res. 2000 May;46(2):286-97. doi: 10.1016/s0008-6363(00)00035-3. [PubMed:10773233 ]
Burjanadze TV: New analysis of the phylogenetic change of collagen thermostability. Biopolymers. 2000 May;53(6):523-8. doi: 10.1002/(SICI)1097-0282(200005)53:6<523::AID-BIP8>3.0.CO;2-7. [PubMed:10775067 ]
Shibasaki T, Mori H, Ozaki A: Enzymatic production of trans-4-hydroxy-L-proline by regio- and stereospecific hydroxylation of L-proline. Biosci Biotechnol Biochem. 2000 Apr;64(4):746-50. doi: 10.1271/bbb.64.746. [PubMed:10830487 ]
Pickersgill IF, Rapoport H: 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. J Org Chem. 2000 Jun 30;65(13):4048-57. doi: 10.1021/jo000071g. [PubMed:10866623 ]
Baldwin JE, Pritchard GJ, Williamson DS: The synthesis of 4-arylsulfanyl-substituted kainoid analogues from trans-4-hydroxy-L-proline. Bioorg Med Chem Lett. 2000 Sep 4;10(17):1927-9. doi: 10.1016/s0960-894x(00)00352-8. [PubMed:10987419 ]
Miskolzie M, Gera L, Stewart JM, Kotovych G: The importance of the N-terminal beta-turn in bradykinin antagonists. J Biomol Struct Dyn. 2000 Oct;18(2):249-60. doi: 10.1080/07391102.2000.10506663. [PubMed:11089646 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. doi: 10.1016/s0899-9007(02)00780-3. [PubMed:12297216 ]
ADAMS E, GOLDSTONE A, SINGH RM, ROSSO G: SUBSTRATE ACTIVITY OF 3-HYDROXYPROLINE ISOMERS FOR ENZYMES ACTIVE WITH 4-HYDROXYPROLINE. Biochim Biophys Acta. 1964 Jul 8;89:164-6. doi: 10.1016/0926-6569(64)90114-2. [PubMed:14212996 ]
Lee HS, Shun CT, Chiou LL, Chen CH, Huang GT, Sheu JC: Hydroxyproline content of needle biopsies as an objective measure of liver fibrosis: Emphasis on sampling variability. J Gastroenterol Hepatol. 2005 Jul;20(7):1109-14. doi: 10.1111/j.1440-1746.2005.03901.x. [PubMed:15955222 ]
Fiorucci S, Rizzo G, Antonelli E, Renga B, Mencarelli A, Riccardi L, Morelli A, Pruzanski M, Pellicciari R: 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. J Pharmacol Exp Ther. 2005 Oct;315(1):58-68. doi: 10.1124/jpet.105.085597. Epub 2005 Jun 24. [PubMed:15980055 ]
Song IK, Kang YK: Conformational preference and cis-trans isomerization of 4(R)-substituted proline residues. J Phys Chem B. 2006 Feb 2;110(4):1915-27. doi: 10.1021/jp054351h. [PubMed:16471763 ]
Kofoed J, Darbre T, Reymond JL: Dual mechanism of zinc-proline catalyzed aldol reactions in water. Chem Commun (Camb). 2006 Apr 14;(14):1482-4. doi: 10.1039/b600703a. Epub 2006 Mar 2. [PubMed:16575434 ]
Keskiaho K, Hieta R, Sormunen R, Myllyharju J: Chlamydomonas reinhardtii has multiple prolyl 4-hydroxylases, one of which is essential for proper cell wall assembly. Plant Cell. 2007 Jan;19(1):256-69. doi: 10.1105/tpc.106.042739. Epub 2007 Jan 12. [PubMed:17220203 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Lee KW, Kim SJ, Park JB, Lee KJ: Relationship between depression anxiety stress scale (DASS) and urinary hydroxyproline and proline concentrations in hospital workers. J Prev Med Public Health. 2011 Jan;44(1):9-13. doi: 10.3961/jpmph.2011.44.1.9. [PubMed:21483218 ]
Nogueira Ade C, Vale RG, Gomes AL, Dantas EH: The effect of muscle actions on the level of connective tissue damage. Res Sports Med. 2011 Oct;19(4):259-70. doi: 10.1080/15438627.2011.608046. [PubMed:21988268 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 4-Hydroxyproline (MMDBc0000770)

MOL for #<Metabolite:0x00007fdb5e8105b0>

3D MOL for #<Metabolite:0x00007fdb5e8105b0>

3D SDF for #<Metabolite:0x00007fdb5e8105b0>

3D-SDF for #<Metabolite:0x00007fdb5e8105b0>

PDB for #<Metabolite:0x00007fdb5e8105b0>

3D PDB for #<Metabolite:0x00007fdb5e8105b0>

SMILES for #<Metabolite:0x00007fdb5e8105b0>

INCHI for #<Metabolite:0x00007fdb5e8105b0>

Structure for #<Metabolite:0x00007fdb5e8105b0>

3D Structure for #<Metabolite:0x00007fdb5e8105b0>