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

2022-08-31 06:12:23 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 3D MOL SDF 3D SDF PDB 3D 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

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

hypro

CAS Registry Number

Not Available

SMILES

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

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

Property	Value	Source
Water Solubility	492 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.7	ChemAxon
logS	0.57	ALOGPS
pKa (Strongest Acidic)	1.64	ChemAxon
pKa (Strongest Basic)	10.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	29.38 m³·mol⁻¹	ChemAxon
Polarizability	12.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000x-0950000000-5b1c397e26b28e872d20	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000x-0950000000-c46b5bba0f41001e3c18	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9530000000-00db00b15ab5341d7d64	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001l-1960000000-abcd0377696d2b52d815	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0590000000-75e03328fb2d44469057	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0950000000-c46b5bba0f41001e3c18	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9530000000-00db00b15ab5341d7d64	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001l-1960000000-abcd0377696d2b52d815	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0940000000-97328204c6b60a244616	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0940000000-468aeb79950a9e6dadc6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-40c0bfa9451caacaf422	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9100000000-af92b4a861832ca4ec13	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-02mu-9670000000-81c8390bdfa262fa9b2f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0019-9700000000-ea3ed008938a57d1263c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014r-9000000000-0b76109525f362b600a0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-477e41e40831316e68ac	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0019-9300000000-7228a10f32d447b58ee0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-11800ca52c6e911f8313	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-11800ca52c6e911f8313	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-1900000000-b6bba00a324b6eab209f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-1900000000-ba9df49a4d967cf8851d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-9000000000-6d125b0bb59101e9ce53	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0019-9300000000-7228a10f32d447b58ee0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0019-9600000000-5bcced64c9dfeb96876f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0019-9600000000-b575fa8df5e2d8bb3a99	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-c036fd15ccf6ed0c554e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-8746de5249187bab94dc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-3f70e8e1eef8568e87ef	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-cd32fa744ef013f5ca48	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-3ea6a86203c48888d528	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-02tc-9000000000-95aa07d1970d7f83f347	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9000000000-95b2178b5433b4b2db50	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-a10576d40ff1d7fc707a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02t9-9400000000-8b66308781907cdf6304	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-7f9d42864b2decdbdd1d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-bfc9154f784caa2e61a7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ar-9800000000-750b3fd4f0e1dcb8ef4c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9000000000-efe39f47f6ee937ded3d	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00ku-9000000000-f5bd67093b2f30a6f62b	2018-05-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001998	Oxoglutaric acid	4-Hydroxyproline	Prolyl 4-hydroxylase, alpha polypeptide i	L-Proline, 2-Oxoglutarate:Oxygen Oxidoreductase (4-Hydroxylating), Endoplasmatic Reticulum	VMH	12714038 2543975 3034602
MMDBr0002623	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NAD+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002624	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NAD+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002625	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NADP+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002626	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NADP+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0005371	4-Hydroxyproline	4-Hydroxyproline	Solute carrier family 6 (proline imino transporter), member 20	Transport of L-Oh-Proline by the Apical Imino Amino Acid Transporters in Kidney And Intestine	VMH	30371894
MMDBr0005419	4-Hydroxyproline	4-Hydroxyproline	Solute carrier family 1 (glutamate/neutral amino acid transporter), member 4	Transport of Hydroxy-Proline	VMH	30371894
MMDBr0005533	4-Hydroxyproline	4-Hydroxyproline	Not Available	Transport of Trans-4-Hydroxy-L-Proline	VMH	30371894
MMDBr0007212	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	Proline dehydrogenase (trans-4-Hydroxy-L-proline)	VMH	30371894
MMDBr0008333	Oxoglutaric acid	4-Hydroxyproline	Not Available	L-Proline,2-oxoglutarate:oxygen oxidoreductase (4-hydroxylating)	VMH	30371894
MMDBr0008342	4-Hydroxyproline	cis-4-Hydroxy-D-proline	Not Available	Trans-4-Hydroxy-L-proline 2-epimerase	VMH	30371894
MMDBr0008356	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	L-hydroxyproline oxidase (NAD), reversible	VMH	30371894
MMDBr0008357	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	L-hydroxyproline oxidase (NADP), reversible	VMH	30371894
MMDBr0010306	Oxoglutaric acid	4-Hydroxyproline	Prolyl 4-hydroxylase, alpha polypeptide i	L-Proline, 2-Oxoglutarate:Oxygen Oxidoreductase (4-Hydroxylating)	VMH	30371894
MMDBr0010307	Oxoglutaric acid	4-Hydroxyproline	Prolyl 4-hydroxylase, alpha polypeptide i	L-Proline, 2-Oxoglutarate:Oxygen Oxidoreductase (4-Hydroxylating)	VMH	30371894
MMDBr0010308	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	HMR_4782	VMH	30371894
MMDBr0010309	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	HMR_4783	VMH	30371894
MMDBr0010989	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	Proline dehydrogenase (trans-4-Hydroxy-L-proline), irreversible	VMH	30371894
MMDBr0012680	4-Hydroxyproline	4-Hydroxyproline	Not Available	trans-4-hydroxy-L-proline transport	VMH	30371894
MMDBr0012681	4-Hydroxyproline	L-D-1-Pyrroline-5-carboxylic acid	Not Available	Hydroxyproline dehydratase	VMH	30371894
MMDBr0014076	4-Hydroxyproline	cis-4-Hydroxy-D-proline	Trans-3-hydroxy-L-proline dehydratase	Epimerization	RHEA	34755880
MMDBr0016751	4-Hydroxyproline	1-Pyrroline-5-carboxylic acid	Trans-4-hydroxy-L-proline dehydratase	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0017980	alpha-Ketoglutarate	Carbon dioxide	L-proline trans-4-hydroxylase	Hydroxylation	RHEA	34755880

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	180	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
Bacteria/NULL	Proteobacteria	3	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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 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

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Showing metabocard for 4-Hydroxyproline (MMDBc0000770)

MOL for #<Metabolite:0x00007f5abca395f8>

3D MOL for #<Metabolite:0x00007f5abca395f8>

3D SDF for #<Metabolite:0x00007f5abca395f8>

3D-SDF for #<Metabolite:0x00007f5abca395f8>

PDB for #<Metabolite:0x00007f5abca395f8>

3D PDB for #<Metabolite:0x00007f5abca395f8>

SMILES for #<Metabolite:0x00007f5abca395f8>

INCHI for #<Metabolite:0x00007f5abca395f8>

Structure for #<Metabolite:0x00007f5abca395f8>

3D Structure for #<Metabolite:0x00007f5abca395f8>