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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-04-16 20:46:48 UTC

Update Date

2023-02-21 17:30:26 UTC

HMDB ID

HMDB0061715

Secondary Accession Numbers

HMDB61715

Metabolite Identification

Common Name

Glutamic acid gamma-methyl ester

Description

L-Glutamic acid 5-methyl ester, also known as poly(gamma-methyl L-glutamate) or PGMGT, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Glutamic acid 5-methyl ester is a very strong 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
L-Glutamate 5-methyl ester	Generator
PGMGT	MeSH
Poly-gamma-methylglutamic acid	MeSH
Poly(gamma-methyl L-glutamate)	MeSH
Poly-gamma-methylglutamate	MeSH
PMLG Polymer	MeSH
Poly(gamma-methyl-L-glutamate)	MeSH
(2S)-2-Amino-5-methoxy-5-oxopentanoate	Generator
(2S)-2-Amino-5-methoxy-5-oxo-pentanoic acid	HMDB
(S)-2-Aminopentanedioic acid 5-methyl ester	HMDB
(S)-Glutamic acid 5-methyl ester	HMDB
4(S)-Carboxy-4-aminobutanoic acid methyl ester	HMDB
5-Methyl L-glutamate	HMDB
Glutamate gamma-methyl ester	HMDB
Glutamate γ-methyl ester	HMDB
Glutamic acid 5-methyl ester	HMDB
L-Glutamic acid gamma-methyl ester	HMDB
L-Glutamic acid γ-methyl ester	HMDB
gamma-Methyl (S)-glutamate	HMDB
gamma-Methyl L-glutamate	HMDB
γ-Methyl (S)-glutamate	HMDB
γ-Methyl L-glutamate	HMDB

Chemical Formula

C₆H₁₁NO₄

Average Molecular Weight

161.1558

Monoisotopic Molecular Weight

161.068807845

IUPAC Name

(2S)-2-amino-5-methoxy-5-oxopentanoic acid

Traditional Name

(2S)-2-amino-5-methoxy-5-oxopentanoic acid

CAS Registry Number

1499-55-4

SMILES

COC(=O)CC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1

InChI Key

ZGEYCCHDTIDZAE-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty acid ester
Fatty acid methyl ester
Dicarboxylic acid or derivatives
Fatty acyl
Methyl ester
Carboxylic acid ester
Amino acid
Carboxylic acid
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Placenta (HMDB: HMDB0061715)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Source

Exogenous

Exogenous (HMDB: HMDB0061715)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.6 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.06 m³·mol⁻¹	ChemAxon
Polarizability	15.51 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	133.191	30932474
DeepCCS	[M-H]-	129.363	30932474
DeepCCS	[M-2H]-	166.55	30932474
DeepCCS	[M+Na]+	142.089	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glutamic acid gamma-methyl ester	COC(=O)CC[C@H](N)C(O)=O	2241.3	Standard polar	33892256
Glutamic acid gamma-methyl ester	COC(=O)CC[C@H](N)C(O)=O	1263.1	Standard non polar	33892256
Glutamic acid gamma-methyl ester	COC(=O)CC[C@H](N)C(O)=O	1597.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutamic acid gamma-methyl ester,1TMS,isomer #1	COC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C	1399.5	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,1TMS,isomer #2	COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O	1499.6	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,2TMS,isomer #1	COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1528.3	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,2TMS,isomer #1	COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1555.4	Standard non polar	33892256
Glutamic acid gamma-methyl ester,2TMS,isomer #1	COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1896.0	Standard polar	33892256
Glutamic acid gamma-methyl ester,2TMS,isomer #2	COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1687.0	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,2TMS,isomer #2	COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1621.1	Standard non polar	33892256
Glutamic acid gamma-methyl ester,2TMS,isomer #2	COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2092.1	Standard polar	33892256
Glutamic acid gamma-methyl ester,3TMS,isomer #1	COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1718.9	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,3TMS,isomer #1	COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1671.7	Standard non polar	33892256
Glutamic acid gamma-methyl ester,3TMS,isomer #1	COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1836.4	Standard polar	33892256
Glutamic acid gamma-methyl ester,1TBDMS,isomer #1	COC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1629.7	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,1TBDMS,isomer #2	COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1742.2	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,2TBDMS,isomer #1	COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1964.7	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,2TBDMS,isomer #1	COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1995.4	Standard non polar	33892256
Glutamic acid gamma-methyl ester,2TBDMS,isomer #1	COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2125.6	Standard polar	33892256
Glutamic acid gamma-methyl ester,2TBDMS,isomer #2	COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2120.4	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,2TBDMS,isomer #2	COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2051.1	Standard non polar	33892256
Glutamic acid gamma-methyl ester,2TBDMS,isomer #2	COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2218.2	Standard polar	33892256
Glutamic acid gamma-methyl ester,3TBDMS,isomer #1	COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2379.3	Semi standard non polar	33892256
Glutamic acid gamma-methyl ester,3TBDMS,isomer #1	COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2292.4	Standard non polar	33892256
Glutamic acid gamma-methyl ester,3TBDMS,isomer #1	COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2195.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamic acid gamma-methyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutamic acid gamma-methyl ester 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 - Glutamic acid gamma-methyl ester 10V, Positive-QTOF	splash10-02ai-2900000000-e25e7bd0169fa84c265a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Positive-QTOF	splash10-014j-9700000000-b2707dfbecef89dccc36	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Positive-QTOF	splash10-0a4i-9000000000-ef9d7dadc9a20b25c7b7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Negative-QTOF	splash10-03di-0900000000-9ca60a4a29b53180d21f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Negative-QTOF	splash10-03fr-3900000000-deb73cb97bd1b4d6f62d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Negative-QTOF	splash10-00ec-9200000000-e28dba9ace5235f5f94d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Negative-QTOF	splash10-01tc-1900000000-7ba8da19d1ca271d51a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Negative-QTOF	splash10-0gx3-6900000000-437a04a8632b8b96a54c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Negative-QTOF	splash10-0006-9000000000-60f58cdb95258ba389a3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Positive-QTOF	splash10-02u9-5900000000-2d2de75bccd5007f24e1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Positive-QTOF	splash10-00lj-9100000000-fac61cb106b5271040ea	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Positive-QTOF	splash10-0a4i-9000000000-677484e9a6c9c097bacc	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

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

61916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68662

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

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Glutamic acid gamma-methyl ester (HMDB0061715)

MOL for HMDB0061715 (Glutamic acid gamma-methyl ester)

3D MOL for HMDB0061715 (Glutamic acid gamma-methyl ester)

3D SDF for HMDB0061715 (Glutamic acid gamma-methyl ester)

3D-SDF for HMDB0061715 (Glutamic acid gamma-methyl ester)

PDB for HMDB0061715 (Glutamic acid gamma-methyl ester)

3D PDB for HMDB0061715 (Glutamic acid gamma-methyl ester)

SMILES for HMDB0061715 (Glutamic acid gamma-methyl ester)

INCHI for HMDB0061715 (Glutamic acid gamma-methyl ester)

Structure for HMDB0061715 (Glutamic acid gamma-methyl ester)

3D Structure for HMDB0061715 (Glutamic acid gamma-methyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra