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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2023-02-21 17:16:10 UTC

HMDB ID

HMDB0002113

Secondary Accession Numbers

HMDB02113

Metabolite Identification

Common Name

3-Hydroxy-L-proline

Description

3-Hydroxy-L-proline 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. 3-Hydroxy-L-proline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxy-L-proline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Hydroxy-L-proline.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
cis-3-Hydroxy-D-proline	ChEBI
Procollagen trans-3-hydroxy-L-proline	HMDB

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

3-hydroxy-L-proline

CAS Registry Number

4298-08-2

SMILES

O[C@H]1CCN[C@H]1C(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1

InChI Key

BJBUEDPLEOHJGE-IUYQGCFVSA-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
D-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyrrolidine
Amino acid
Secondary alcohol
Carboxylic acid
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	431 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.7	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	1.61	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	12.27 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.912	31661259
DarkChem	[M-H]-	122.843	31661259
DeepCCS	[M+H]+	123.422	30932474
DeepCCS	[M-H]-	119.555	30932474
DeepCCS	[M-2H]-	156.946	30932474
DeepCCS	[M+Na]+	132.435	30932474
AllCCS	[M+H]+	129.0	32859911
AllCCS	[M+H-H2O]+	124.4	32859911
AllCCS	[M+NH4]+	133.4	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	121.8	32859911
AllCCS	[M+Na-2H]-	123.8	32859911
AllCCS	[M+HCOO]-	126.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-L-proline	O[C@H]1CCN[C@H]1C(O)=O	2479.0	Standard polar	33892256
3-Hydroxy-L-proline	O[C@H]1CCN[C@H]1C(O)=O	1274.6	Standard non polar	33892256
3-Hydroxy-L-proline	O[C@H]1CCN[C@H]1C(O)=O	1502.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-L-proline,1TMS,isomer #1	C[Si](C)(C)O[C@H]1CCN[C@H]1C(=O)O	1408.6	Semi standard non polar	33892256
3-Hydroxy-L-proline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O	1346.0	Semi standard non polar	33892256
3-Hydroxy-L-proline,1TMS,isomer #3	C[Si](C)(C)N1CC[C@H](O)[C@@H]1C(=O)O	1414.9	Semi standard non polar	33892256
3-Hydroxy-L-proline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O[Si](C)(C)C	1444.3	Semi standard non polar	33892256
3-Hydroxy-L-proline,2TMS,isomer #2	C[Si](C)(C)O[C@H]1CCN([Si](C)(C)C)[C@H]1C(=O)O	1466.8	Semi standard non polar	33892256
3-Hydroxy-L-proline,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H]1[C@@H](O)CCN1[Si](C)(C)C	1421.3	Semi standard non polar	33892256
3-Hydroxy-L-proline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C	1503.2	Semi standard non polar	33892256
3-Hydroxy-L-proline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C	1566.1	Standard non polar	33892256
3-Hydroxy-L-proline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CCN1[Si](C)(C)C	1653.9	Standard polar	33892256
3-Hydroxy-L-proline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CCN[C@H]1C(=O)O	1671.2	Semi standard non polar	33892256
3-Hydroxy-L-proline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O	1588.8	Semi standard non polar	33892256
3-Hydroxy-L-proline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC[C@H](O)[C@@H]1C(=O)O	1691.3	Semi standard non polar	33892256
3-Hydroxy-L-proline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1NCC[C@@H]1O[Si](C)(C)C(C)(C)C	1898.5	Semi standard non polar	33892256
3-Hydroxy-L-proline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CCN([Si](C)(C)C(C)(C)C)[C@H]1C(=O)O	1939.3	Semi standard non polar	33892256
3-Hydroxy-L-proline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O)CCN1[Si](C)(C)C(C)(C)C	1912.2	Semi standard non polar	33892256
3-Hydroxy-L-proline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C	2181.5	Semi standard non polar	33892256
3-Hydroxy-L-proline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C	2192.3	Standard non polar	33892256
3-Hydroxy-L-proline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1[Si](C)(C)C(C)(C)C	2076.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9000000000-b543b8f19baf933e2510	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-8920000000-a1f57d10065421ae5629	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-L-proline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Positive-QTOF	splash10-03e9-2900000000-128ccf9715c5890c5404	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Positive-QTOF	splash10-03xr-9600000000-8c3c68532a2b86bfd028	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Positive-QTOF	splash10-0fr6-9000000000-d018e434f138775d4120	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Negative-QTOF	splash10-001r-7900000000-3230ec745853fb03ffc2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Negative-QTOF	splash10-02u9-9300000000-8240d8b2c6fddad07085	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Negative-QTOF	splash10-0673-9000000000-a3fea27c28e95706d0ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Positive-QTOF	splash10-000i-9400000000-f8803de3984022a6de11	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Positive-QTOF	splash10-00kr-9000000000-7199742da3eaa66ad564	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Positive-QTOF	splash10-00kf-9000000000-f8bbde6aa62a6d9afa3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 10V, Negative-QTOF	splash10-001i-1900000000-df968a68e6f2ab76adc2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 20V, Negative-QTOF	splash10-0006-9200000000-c73aa9b436f74ef75e9c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-L-proline 40V, Negative-QTOF	splash10-052f-9000000000-08bc65f1f17e8bcb3d04	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112177

KNApSAcK ID

Not Available

Chemspider ID

9312313

KEGG Compound ID

C04397

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6494

PubChem Compound

11137200

PDB ID

Not Available

ChEBI ID

87840

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sinha, Surajit; Tilve, Santosh; Chandrasekaran, Srinivasan. A convenient synthesis of trans-3-hydroxy-L-proline. ARKIVOC (Gainesville, FL, United States) (2005), (11), 209-217.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Prolyl 3-hydroxylase 1

General function:: Involved in oxidoreductase activity
Specific function:: Basement membrane-associated chondroitin sulfate proteoglycan (CSPG). Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens, especially types IV and V. May be involved in the secretory pathway of cells. Has growth suppressive activity in fibroblasts.
Gene Name:: LEPRE1
Uniprot ID:: Q32P28
Molecular weight:: 78921.41

Enzyme Details

2. Prolyl 3-hydroxylase 2

General function:: Involved in oxidoreductase activity
Specific function:: Shows prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types II, IV and V (By similarity).
Gene Name:: LEPREL1
Uniprot ID:: Q8IVL5
Molecular weight:: 60386.32

Enzyme Details

3. Prolyl 3-hydroxylase 3

General function:: Involved in iron ion binding
Specific function:: Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types IV and V (By similarity).
Gene Name:: LEPREL2
Uniprot ID:: Q8IVL6
Molecular weight:: 81835.705

Showing metabocard for 3-Hydroxy-L-proline (HMDB0002113)

MOL for HMDB0002113 (3-Hydroxy-L-proline)

3D MOL for HMDB0002113 (3-Hydroxy-L-proline)

3D SDF for HMDB0002113 (3-Hydroxy-L-proline)

3D-SDF for HMDB0002113 (3-Hydroxy-L-proline)

PDB for HMDB0002113 (3-Hydroxy-L-proline)

3D PDB for HMDB0002113 (3-Hydroxy-L-proline)

SMILES for HMDB0002113 (3-Hydroxy-L-proline)

INCHI for HMDB0002113 (3-Hydroxy-L-proline)

Structure for HMDB0002113 (3-Hydroxy-L-proline)

3D Structure for HMDB0002113 (3-Hydroxy-L-proline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes