MiMeDB: Showing metabocard for cis-4-hydroxy-L-proline (MMDBc0054396)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:10:31 UTC

Update Date

2025-10-07 16:08:30 UTC

Metabolite ID

MMDBc0054396

Metabolite Identification

Common Name

cis-4-hydroxy-L-proline

Description

cis-4-hydroxy-L-proline is a non-proteinogenic amino acid classified as a hydroxyproline derivative. Its chemical structure features a hydroxyl group at the fourth carbon of the proline ring, which adopts a cis configuration, contributing to its unique properties. This compound is involved in several biochemical pathways, primarily through its conversion from 4-oxo-L-proline, catalyzed by the enzyme BDH2, which has been shown to have anticancer activity (PMID:39883584 ). The reaction equilibrium strongly favors the formation of cis-4-hydroxy-L-proline (PMID:39883584 ). Additionally, BDH2 functions as a dehydrogenase for cis-4-hydroxy-L-proline, highlighting its role in metabolic processes (PMID:38918500 ). This metabolite also participates in a pathway where it is isomerized to trans-4-hydroxy-L-proline and subsequently undergoes radical-mediated ring opening (PMID:35611954 ). Furthermore, studies have demonstrated that cis-4-hydroxy-L-proline can selectively cage alkali metal ions, showcasing its potential applications in supramolecular chemistry (PMID:37584166 ). The compound's utility is further illustrated by its role as a chiral organocatalyst, providing high stereocontrol in synthetic reactions (PMID:37181764 ).

Structure

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

Synonyms

Value	Source
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylic acid	ChEBI
4-cis-L-Hydroxyproline	ChEBI
Allo-4-hydroxy-L-proline	ChEBI
L-Allo-hydroxyproline	ChEBI
L-cis-4-Hydroxyproline	ChEBI
L-Allohydroxyproline	Kegg
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylate	Generator
cis-4-Hydroxy-L-proline	HMDB
cis-Hydroxyproline	HMDB
(4S)-4-Hydroxy-L-proline	HMDB
(2S,4S)-4-Hydroxyproline	HMDB
(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid	HMDB
(S)-allo-Hydroxyproline	HMDB
4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acid	HMDB
4-cis-Hydroxy-L-proline	HMDB
4-allo-Hydroxyproline	HMDB
L-allo-4-Hydroxyproline	HMDB
allo-4-Hydroxyproline	HMDB
allo-Hydroxy-L-proline	HMDB
allo-L-Hydroxyproline	HMDB
H-cis-Hyp-OH	HMDB
NSC 206274	HMDB
cis-4-Hydroxyproline	HMDB, MeSH
Hydroxyproline	MeSH, HMDB
4 Hydroxyproline	MeSH, HMDB
4-Hydroxyproline	MeSH, HMDB
Oxyproline	MeSH, HMDB
cis 4 Hydroxyproline	MeSH, HMDB

Molecular Formula

C₅H₉NO₃

Average Mass

131.1299

Monoisotopic Mass

131.058243159

IUPAC Name

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

Traditional Name

L-hydroxyproline

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)CN[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-/m0/s1

InChI Key

PMMYEEVYMWASQN-IMJSIDKUSA-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

non-proteinogenic L-alpha-amino acid (CHEBI:28397 )
4-hydroxyproline (CHEBI:28397 )

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	12.22 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-b23d222f2dfeb06049c3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-80dde78ab7695bc1272a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-6f9557455a7abfe0faea	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-54b8ac52a265772761b5	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02t9-9400000000-8302666cfee04dd777ff	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-94ec52ef1a3baca29ced	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-276917674ec7e7c3d6db	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03yi-7900000000-dbe7a1905f8ee1beda93	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-cec6276d54ed5d3a5424	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-3900000000-206002d6953f7b8754ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03y0-9600000000-624dbd787acc76434f16	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-73f483e220b16df3a0ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03yr-4900000000-956289a1f2420b73ca3d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9100000000-b31bfff7a750b532e918	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9000000000-9473acfa9148a036c0ba	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	491.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	404.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	40.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	221.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	291.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	320.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	433.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	861.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	799.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	190.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	508.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	206.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	39.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	367.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	756.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	80.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	307.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	664.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	564.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_1	C[Si](C)(C)O[C@@H]1CN[C@H](C(=O)O)C1	standard non polar	2025-10-24	1789.64
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_2	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1	standard non polar	2025-10-24	2006.68
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_3	C[Si](C)(C)N1C[C@@H](O)C[C@H]1C(=O)O	standard non polar	2025-10-24	1745.48
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_4	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1	standard non polar	2025-10-24	1820.45
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_5	C[Si](C)(C)O[C@H]1C[C@@H](C(=O)O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	2282.79
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_6	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1[Si](C)(C)C	standard non polar	2025-10-24	2248.27
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_7	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C	standard non polar	2025-10-24	1904.11
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_1	C[Si](C)(C)O[C@@H]1CN[C@H](C(=O)O)C1	standard polar	2025-10-24	2354.86
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_2	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1	standard polar	2025-10-24	1918.78
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_3	C[Si](C)(C)N1C[C@@H](O)C[C@H]1C(=O)O	standard polar	2025-10-24	1741.43
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_4	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1	standard polar	2025-10-24	2269.98
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_5	C[Si](C)(C)O[C@H]1C[C@@H](C(=O)O)N([Si](C)(C)C)C1	standard polar	2025-10-24	2113.65
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_6	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1[Si](C)(C)C	standard polar	2025-10-24	2208.42
Gas Chromatography	cis-4-hydroxy-L-proline_TMS_7	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C	standard polar	2025-10-24	1726.83

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	3	Human ; Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0240251

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28397

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for cis-4-hydroxy-L-proline (MMDBc0054396)

MOL for #<Metabolite:0x00007fadfc064f30>

3D MOL for #<Metabolite:0x00007fadfc064f30>

3D SDF for #<Metabolite:0x00007fadfc064f30>

3D-SDF for #<Metabolite:0x00007fadfc064f30>

PDB for #<Metabolite:0x00007fadfc064f30>

3D PDB for #<Metabolite:0x00007fadfc064f30>

SMILES for #<Metabolite:0x00007fadfc064f30>

INCHI for #<Metabolite:0x00007fadfc064f30>

Structure for #<Metabolite:0x00007fadfc064f30>

3D Structure for #<Metabolite:0x00007fadfc064f30>