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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-30 20:56:21 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240251

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cis-4-Hydroxyproline

Description

cis 4-Hydroxyproline, also known as L-allo-hydroxyproline, 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. cis 4-Hydroxyproline is found, on average, in the highest concentration within a few different foods, such as oats (Avena sativa), ryes (Secale cereale), and wheats (Triticum) and in a lower concentration in white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.), red bell peppers (Capsicum annuum), and garden onions (Allium cepa). cis 4-Hydroxyproline has also been detected, but not quantified in, green bell peppers (Capsicum annuum). This could make cis 4-hydroxyproline a potential biomarker for the consumption of these foods. cis 4-Hydroxyproline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on cis 4-Hydroxyproline.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

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

Traditional Name

L-hydroxyproline

CAS Registry Number

618-27-9

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-/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 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	126.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001744
[M+H]+	Not Available	128.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001744

Predicted Molecular 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	12.22 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	127.14	31661259
DarkChem	[M-H]-	124.663	31661259
DeepCCS	[M+H]+	126.135	30932474
DeepCCS	[M-H]-	123.267	30932474
DeepCCS	[M-2H]-	160.018	30932474
DeepCCS	[M+Na]+	135.416	30932474
AllCCS	[M+H]+	129.3	32859911
AllCCS	[M+H-H2O]+	124.7	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.7	32859911
AllCCS	[M-H]-	123.0	32859911
AllCCS	[M+Na-2H]-	125.1	32859911
AllCCS	[M+HCOO]-	127.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-4-Hydroxyproline	O[C@@H]1CN[C@@H](C1)C(O)=O	2552.8	Standard polar	33892256
cis-4-Hydroxyproline	O[C@@H]1CN[C@@H](C1)C(O)=O	1284.4	Standard non polar	33892256
cis-4-Hydroxyproline	O[C@@H]1CN[C@@H](C1)C(O)=O	1552.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-4-Hydroxyproline,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1CN[C@H](C(=O)O)C1	1449.4	Semi standard non polar	33892256
cis-4-Hydroxyproline,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1	1354.4	Semi standard non polar	33892256
cis-4-Hydroxyproline,1TMS,isomer #3	C[Si](C)(C)N1C[C@@H](O)C[C@H]1C(=O)O	1432.0	Semi standard non polar	33892256
cis-4-Hydroxyproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1	1442.1	Semi standard non polar	33892256
cis-4-Hydroxyproline,2TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@@H](C(=O)O)N([Si](C)(C)C)C1	1471.9	Semi standard non polar	33892256
cis-4-Hydroxyproline,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1[Si](C)(C)C	1442.8	Semi standard non polar	33892256
cis-4-Hydroxyproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C	1500.8	Semi standard non polar	33892256
cis-4-Hydroxyproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C	1594.0	Standard non polar	33892256
cis-4-Hydroxyproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C)CN1[Si](C)(C)C	1683.5	Standard polar	33892256
cis-4-Hydroxyproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1CN[C@H](C(=O)O)C1	1682.0	Semi standard non polar	33892256
cis-4-Hydroxyproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1	1602.4	Semi standard non polar	33892256
cis-4-Hydroxyproline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C[C@@H](O)C[C@H]1C(=O)O	1698.2	Semi standard non polar	33892256
cis-4-Hydroxyproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1	1905.5	Semi standard non polar	33892256
cis-4-Hydroxyproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)C1	1989.8	Semi standard non polar	33892256
cis-4-Hydroxyproline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O)CN1[Si](C)(C)C(C)(C)C	1919.3	Semi standard non polar	33892256
cis-4-Hydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C	2197.5	Semi standard non polar	33892256
cis-4-Hydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C	2189.9	Standard non polar	33892256
cis-4-Hydroxyproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)CN1[Si](C)(C)C(C)(C)C	2100.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cis-4-Hydroxyproline 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Positive-QTOF	splash10-014l-9000000000-b23d222f2dfeb06049c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Positive-QTOF	splash10-000i-9200000000-80dde78ab7695bc1272a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Positive-QTOF	splash10-00kr-9000000000-6f9557455a7abfe0faea	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Positive-QTOF	splash10-03di-3900000000-54b8ac52a265772761b5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Positive-QTOF	splash10-02t9-9400000000-8302666cfee04dd777ff	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Positive-QTOF	splash10-014l-9000000000-94ec52ef1a3baca29ced	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Negative-QTOF	splash10-001i-2900000000-276917674ec7e7c3d6db	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Negative-QTOF	splash10-03yi-7900000000-dbe7a1905f8ee1beda93	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Negative-QTOF	splash10-00kf-9000000000-cec6276d54ed5d3a5424	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Negative-QTOF	splash10-01q9-3900000000-206002d6953f7b8754ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Negative-QTOF	splash10-03y0-9600000000-624dbd787acc76434f16	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Negative-QTOF	splash10-0006-9000000000-73f483e220b16df3a0ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 10V, Positive-QTOF	splash10-03yr-4900000000-956289a1f2420b73ca3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 20V, Positive-QTOF	splash10-014i-9100000000-b31bfff7a750b532e918	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyproline 40V, Positive-QTOF	splash10-0aou-9000000000-9473acfa9148a036c0ba	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart 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

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for cis-4-Hydroxyproline (HMDB0240251)

MOL for HMDB0240251 (cis-4-Hydroxyproline)

3D MOL for HMDB0240251 (cis-4-Hydroxyproline)

3D SDF for HMDB0240251 (cis-4-Hydroxyproline)

3D-SDF for HMDB0240251 (cis-4-Hydroxyproline)

PDB for HMDB0240251 (cis-4-Hydroxyproline)

3D PDB for HMDB0240251 (cis-4-Hydroxyproline)

SMILES for HMDB0240251 (cis-4-Hydroxyproline)

INCHI for HMDB0240251 (cis-4-Hydroxyproline)

Structure for HMDB0240251 (cis-4-Hydroxyproline)

3D Structure for HMDB0240251 (cis-4-Hydroxyproline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra