Livestock Metabolome Database: Showing metabocard for 4-Hydroxyproline (LMDB00230)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:13 UTC

Update Date

2021-04-30 22:07:55 UTC

Lmdb

LMDB00230

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxyproline

Description

4-Hydroxyproline (or 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 amino acid. Hydroxyproline and proline play key roles for 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 ).

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

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

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

Traditional Name

hypro

CAS Registry Number

51-35-4

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	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	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	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	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001l-1960000000-abcd0377696d2b52d815	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0590000000-75e03328fb2d44469057	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0950000000-c46b5bba0f41001e3c18	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9530000000-00db00b15ab5341d7d64	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001l-1960000000-abcd0377696d2b52d815	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0940000000-97328204c6b60a244616	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0940000000-468aeb79950a9e6dadc6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-40c0bfa9451caacaf422	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9100000000-af92b4a861832ca4ec13	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-02mu-9670000000-81c8390bdfa262fa9b2f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0019-9700000000-ea3ed008938a57d1263c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014r-9000000000-0b76109525f362b600a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-477e41e40831316e68ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0019-9300000000-7228a10f32d447b58ee0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-11800ca52c6e911f8313	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-11800ca52c6e911f8313	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-1900000000-b6bba00a324b6eab209f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-1900000000-ba9df49a4d967cf8851d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-9000000000-6d125b0bb59101e9ce53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0019-9300000000-7228a10f32d447b58ee0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0019-9600000000-5bcced64c9dfeb96876f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0019-9600000000-b575fa8df5e2d8bb3a99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-c036fd15ccf6ed0c554e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-8746de5249187bab94dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-3f70e8e1eef8568e87ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-cd32fa744ef013f5ca48	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-3ea6a86203c48888d528	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-02tc-9000000000-95aa07d1970d7f83f347	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9000000000-95b2178b5433b4b2db50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-a10576d40ff1d7fc707a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02t9-9400000000-8b66308781907cdf6304	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-7f9d42864b2decdbdd1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-bfc9154f784caa2e61a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ar-9800000000-750b3fd4f0e1dcb8ef4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9000000000-efe39f47f6ee937ded3d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00ku-9000000000-f5bd67093b2f30a6f62b	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Plasma
Serum
Synovial Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	70 +/- 10-80+/-0 uM	Not Available	Porcine	183842	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Plasma	Detected and Quantified	14.8 uM	Not Available	Bovine	17197001	details
Plasma	Detected and Quantified	19.3 uM	Not Available	Bovine	17197001	details
Plasma	Detected and Quantified	23.4 uM	Not Available	Bovine	17197001	details
Plasma	Detected and Quantified	13.2 +/- 5.6 uM	Not Available	Ovine	17900638	details
Plasma	Detected and Quantified	21.9-25.5 uM	Not Available	Ovine	17900638	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Plasma	Detected and Quantified	123 +/- 7-90+/-14 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	166 +/- 6-82+/-9 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	40 +/- 3-43+/-5 uM	Not Available	Porcine	22513987	details
Serum	Detected and Quantified	72.829 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	57.271 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	46.671 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	81.751 uM	Not Available	Porcine	26020888	details
Serum	Detected and Quantified	16.0131 +/- 5.3477 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.9396 +/- 5.0071 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.3492 +/- 5.615 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.8733 +/- 2.9334 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.1965 +/- 6.4661 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.25 +/- 4.782 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.3372 +/- 3.4498 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.0354 +/- 4.0511 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.0569 +/- 5.6949 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.9152 +/- 6.8091 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.1192 +/- 5.0963 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.1852 +/- 3.3619 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	59.52 +/- 28.33 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.00822 +/- 0.000496 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	0.00630 +/- 0.000503 uM	Not Available	Porcine	19847666	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details

External Links

DrugBank ID

DB08847

HMDB ID

HMDB0000725

FooDB ID

FDB013511

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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. [436278 ]
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. [10706420 ]
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. [21988268 ]
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. [21483218 ]

Showing metabocard for 4-Hydroxyproline (LMDB00230)

Structure for LMDB00230 (4-Hydroxyproline)