Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 04:33:12 UTC

Update Date

2023-02-21 17:31:01 UTC

HMDB ID

HMDB0062585

Secondary Accession Numbers

HMDB62585

Metabolite Identification

Common Name

(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid

Description

(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic acid, also known as 3-hydroxy-L-1-pyrroline-5-carboxylate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic acid is a moderately basic compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R,5S)-1-Pyrroline-3-hydroxy-5-carboxylate	ChEBI
3-Hydroxy-L-1-pyrroline-5-carboxylate	ChEBI
L-1-Pyrroline-3-hydroxy-5-carboxylate	ChEBI
(3R,5S)-3-Hydroxy-1-pyrroline-5-carboxylate	Kegg
3-Hydroxy-L-1-pyrroline-5-carboxylic acid	Generator
L-1-Pyrroline-3-hydroxy-5-carboxylic acid	Generator
(3R,5S)-3-Hydroxy-1-pyrroline-5-carboxylic acid	Generator

Chemical Formula

C₅H₇NO₃

Average Molecular Weight

129.115

Monoisotopic Molecular Weight

129.042593089

IUPAC Name

(2S,4R)-4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid

Traditional Name

(2S,4R)-4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)/t3-,4+/m1/s1

InChI Key

WFOFKRKDDKGRIK-DMTCNVIQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Pyrroline
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Alcohol
Imine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

1-pyrroline-3-hydroxy-5-carboxylic acid (CHEBI:6151 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062585)

Process

Not Available

Role

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	33.9 g/l	ALOGPS
LogP	-1.10	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-1.5	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	2.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.85 m³·mol⁻¹	ChemAxon
Polarizability	11.59 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]+	126.95	31661259
DarkChem	[M-H]-	124.429	31661259
DeepCCS	[M+H]+	128.341	30932474
DeepCCS	[M-H]-	126.097	30932474
DeepCCS	[M-2H]-	160.185	30932474
DeepCCS	[M+Na]+	134.58	30932474
AllCCS	[M+H]+	128.8	32859911
AllCCS	[M+H-H2O]+	124.1	32859911
AllCCS	[M+NH4]+	133.2	32859911
AllCCS	[M+Na]+	134.4	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
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid	[H][C@@]1(O)C[C@]([H])(N=C1)C(O)=O	2115.1	Standard polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid	[H][C@@]1(O)C[C@]([H])(N=C1)C(O)=O	1211.9	Standard non polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid	[H][C@@]1(O)C[C@]([H])(N=C1)C(O)=O	1337.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid,1TMS,isomer #1	C[Si](C)(C)O[C@H]1C=N[C@H](C(=O)O)C1	1396.3	Semi standard non polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)C=N1	1281.4	Semi standard non polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C)C=N1	1400.8	Semi standard non polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C=N[C@H](C(=O)O)C1	1622.6	Semi standard non polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O)C=N1	1528.7	Semi standard non polar	33892256
(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)C=N1	1830.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-10791163f3a1cf763a5f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-5910000000-0d5241ee660e7a60b0f9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 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 - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 10V, Positive-QTOF	splash10-03di-2900000000-55a55879516c98fc53d7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 20V, Positive-QTOF	splash10-03e9-9700000000-0a05c354b785d2647ab4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 40V, Positive-QTOF	splash10-0f6x-9000000000-787b98c69cde66cc3807	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 10V, Negative-QTOF	splash10-004i-2900000000-9e076288ac797c9e7292	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 20V, Negative-QTOF	splash10-040r-7900000000-f4afe5bb07de1a9e9865	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 40V, Negative-QTOF	splash10-015c-9000000000-e32ba0243d3ab8a41022	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 10V, Positive-QTOF	splash10-001i-9300000000-c26ff3ebe1bb758e5252	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 20V, Positive-QTOF	splash10-053r-9000000000-97da4a76921516901d46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 40V, Positive-QTOF	splash10-0pc3-9000000000-8982b409276eceb00f1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 10V, Negative-QTOF	splash10-004i-0900000000-06e1bd2d2793c5f0afaa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 20V, Negative-QTOF	splash10-0059-9400000000-a84600f4fc13459b9448	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid 40V, Negative-QTOF	splash10-0006-9000000000-d2c2d7b1e05ce54b0932	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04281

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966267

PDB ID

Not Available

ChEBI ID

6151

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 (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid (HMDB0062585)

MOL for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

3D MOL for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

3D SDF for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

3D-SDF for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

PDB for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

3D PDB for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

SMILES for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

INCHI for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

Structure for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

3D Structure for HMDB0062585 ((3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic Acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra