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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:24 UTC

Update Date

2023-02-21 17:18:46 UTC

HMDB ID

HMDB0029434

Secondary Accession Numbers

HMDB29434

Metabolite Identification

Common Name

(±)-4-Methylene-2-pyrrolidinecarboxylic acid

Description

(±)-4-Methylene-2-pyrrolidinecarboxylic acid, also known as 4-methylene-L-proline or 4-methylidenepyrrolidine-2-carboxylate, 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 (±)-4-Methylene-2-pyrrolidinecarboxylic acid has been detected, but not quantified in, fruits. This could make (±)-4-methylene-2-pyrrolidinecarboxylic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-4-Methylene-2-pyrrolidinecarboxylic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(±)-4-methylene-2-pyrrolidinecarboxylate	Generator
4-Methyleneproline, (DL)-isomer	HMDB
4-Methylene-L-proline	HMDB
4-Methylidenepyrrolidine-2-carboxylate	HMDB
4-Methyleneproline	HMDB

Chemical Formula

C₆H₉NO₂

Average Molecular Weight

127.1412

Monoisotopic Molecular Weight

127.063328537

IUPAC Name

4-methylidenepyrrolidine-2-carboxylic acid

Traditional Name

4-methylidenepyrrolidine-2-carboxylic acid

CAS Registry Number

2370-38-9

SMILES

OC(=O)C1CC(=C)CN1

InChI Identifier

InChI=1S/C6H9NO2/c1-4-2-5(6(8)9)7-3-4/h5,7H,1-3H2,(H,8,9)

InChI Key

PEYQZZMUNYLHII-UHFFFAOYSA-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
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Amino acid
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029434)
Cytoplasm (HMDB: HMDB0029434)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	224 - 245 °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	177 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.5	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	10.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.24 m³·mol⁻¹	ChemAxon
Polarizability	12.69 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]+	127.037	31661259
DarkChem	[M-H]-	120.862	31661259
DeepCCS	[M+H]+	124.141	30932474
DeepCCS	[M-H]-	120.629	30932474
DeepCCS	[M-2H]-	157.921	30932474
DeepCCS	[M+Na]+	132.93	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	122.9	32859911
AllCCS	[M+NH4]+	132.0	32859911
AllCCS	[M+Na]+	133.3	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	126.9	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-4-Methylene-2-pyrrolidinecarboxylic acid	OC(=O)C1CC(=C)CN1	2031.3	Standard polar	33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid	OC(=O)C1CC(=C)CN1	1101.4	Standard non polar	33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid	OC(=O)C1CC(=C)CN1	1312.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TMS,isomer #1	C=C1CNC(C(=O)O[Si](C)(C)C)C1	1241.3	Semi standard non polar	33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TMS,isomer #2	C=C1CC(C(=O)O)N([Si](C)(C)C)C1	1311.8	Semi standard non polar	33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TMS,isomer #1	C=C1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C1	1337.2	Semi standard non polar	33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TMS,isomer #1	C=C1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C1	1342.4	Standard non polar	33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TBDMS,isomer #1	C=C1CNC(C(=O)O[Si](C)(C)C(C)(C)C)C1	1450.6	Semi standard non polar	33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TBDMS,isomer #2	C=C1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)C1	1545.4	Semi standard non polar	33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TBDMS,isomer #1	C=C1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1	1771.8	Semi standard non polar	33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TBDMS,isomer #1	C=C1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1	1765.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-358a6914480ac6e64ab7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9100000000-7cd7f99b38507da01915	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic 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 - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Positive-QTOF	splash10-004i-3900000000-9274706ee64020acc143	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Positive-QTOF	splash10-001i-9300000000-03ef1e475ad33bba3ee0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Positive-QTOF	splash10-0pvl-9000000000-c818f95849c168eb02e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Negative-QTOF	splash10-004i-2900000000-7c89ea5165a6365aee8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Negative-QTOF	splash10-003r-9700000000-ab38f832cb8b8e41a4e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Negative-QTOF	splash10-0fsr-9000000000-4abd3484276ce24f4d0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Positive-QTOF	splash10-001i-9000000000-2431731543c23668dd16	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Positive-QTOF	splash10-001i-9000000000-6fedfb706f5c40e6ed18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Positive-QTOF	splash10-001c-9000000000-7661f522e86e11d63fe1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Negative-QTOF	splash10-004i-0900000000-92dabc7e1e831e6f3847	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Negative-QTOF	splash10-003r-9800000000-711e14a5b1a54935c187	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Negative-QTOF	splash10-0006-9000000000-1f1ec61dcf07e73774b4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

Cytoplasm
Extracellular

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

FDB000538

KNApSAcK ID

C00050723

Chemspider ID

485385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

558375

PDB ID

Not Available

ChEBI ID

Not Available

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-4-Methylene-2-pyrrolidinecarboxylic acid (HMDB0029434)

MOL for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

3D MOL for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

3D SDF for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

3D-SDF for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

PDB for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

3D PDB for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

SMILES for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

INCHI for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

Structure for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

3D Structure for HMDB0029434 ((±)-4-Methylene-2-pyrrolidinecarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra