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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:00:28 UTC

Update Date

2021-09-26 23:05:46 UTC

HMDB ID

HMDB0252887

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glycylsarcosine

Description

glycylsarcosine zwitterion, also known as glycyl-sarcosine, belongs to the class of organic compounds known as peptoid-peptide hybrids. Peptoid-peptide hybrids are compounds containing a peptoid-peptide backbone, which consists alternating amino acid and n-substituted amino acids linked to each other by a peptide bond. glycylsarcosine zwitterion is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Glycylsarcosine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Glycylsarcosine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gly-sar zwitterion	ChEBI
Glycyl-N-methylglycine zwitterion	ChEBI
Glycyl-sarcosine	ChEBI
Glycyl-sarcosine zwitterion	ChEBI
N-Glycyl-N-methylglycine zwitterion	ChEBI
N-Glycylsarcosine zwitterion	ChEBI
Gly-sar	MeSH

Chemical Formula

C₅H₁₀N₂O₃

Average Molecular Weight

146.146

Monoisotopic Molecular Weight

146.06914219

IUPAC Name

2-(2-amino-N-methylacetamido)acetic acid

Traditional Name

(2-amino-N-methylacetamido)acetic acid

CAS Registry Number

Not Available

SMILES

CN(CC(O)=O)C(=O)CN

InChI Identifier

InChI=1S/C5H10N2O3/c1-7(3-5(9)10)4(8)2-6/h2-3,6H2,1H3,(H,9,10)

InChI Key

VYAMLSCELQQRAE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptoid-peptide hybrids. Peptoid-peptide hybrids are compounds containing a peptoid-peptide backbone, which consists alternating amino acid and n-substituted amino acids linked to each other by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Peptoid-peptide hybrids

Direct Parent

Peptoid-peptide hybrids

Alternative Parents

Substituents

Peptoid/peptide hybrid
Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Organic oxygen compound
Primary amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	-2.8	ALOGPS
logP	-4.3	ChemAxon
logS	0.16	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.7 m³·mol⁻¹	ChemAxon
Polarizability	13.8 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]+	128.714	30932474
DeepCCS	[M-H]-	125.771	30932474
DeepCCS	[M-2H]-	162.686	30932474
DeepCCS	[M+Na]+	137.942	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.6	32859911
AllCCS	[M-H]-	127.6	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycylsarcosine	CN(CC(O)=O)C(=O)CN	2087.6	Standard polar	33892256
Glycylsarcosine	CN(CC(O)=O)C(=O)CN	1449.0	Standard non polar	33892256
Glycylsarcosine	CN(CC(O)=O)C(=O)CN	1538.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycylsarcosine,2TMS,isomer #1	CN(CC(=O)O[Si](C)(C)C)C(=O)CN[Si](C)(C)C	1667.2	Semi standard non polar	33892256
Glycylsarcosine,2TMS,isomer #1	CN(CC(=O)O[Si](C)(C)C)C(=O)CN[Si](C)(C)C	1626.6	Standard non polar	33892256
Glycylsarcosine,2TMS,isomer #1	CN(CC(=O)O[Si](C)(C)C)C(=O)CN[Si](C)(C)C	1987.3	Standard polar	33892256
Glycylsarcosine,2TMS,isomer #2	CN(CC(=O)O)C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1740.9	Semi standard non polar	33892256
Glycylsarcosine,2TMS,isomer #2	CN(CC(=O)O)C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1712.4	Standard non polar	33892256
Glycylsarcosine,2TMS,isomer #2	CN(CC(=O)O)C(=O)CN([Si](C)(C)C)[Si](C)(C)C	2074.0	Standard polar	33892256
Glycylsarcosine,3TMS,isomer #1	CN(CC(=O)O[Si](C)(C)C)C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1808.3	Semi standard non polar	33892256
Glycylsarcosine,3TMS,isomer #1	CN(CC(=O)O[Si](C)(C)C)C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1751.4	Standard non polar	33892256
Glycylsarcosine,3TMS,isomer #1	CN(CC(=O)O[Si](C)(C)C)C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1828.7	Standard polar	33892256
Glycylsarcosine,2TBDMS,isomer #1	CN(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CN[Si](C)(C)C(C)(C)C	2143.5	Semi standard non polar	33892256
Glycylsarcosine,2TBDMS,isomer #1	CN(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CN[Si](C)(C)C(C)(C)C	2040.9	Standard non polar	33892256
Glycylsarcosine,2TBDMS,isomer #1	CN(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CN[Si](C)(C)C(C)(C)C	2153.8	Standard polar	33892256
Glycylsarcosine,2TBDMS,isomer #2	CN(CC(=O)O)C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2182.9	Semi standard non polar	33892256
Glycylsarcosine,2TBDMS,isomer #2	CN(CC(=O)O)C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2106.0	Standard non polar	33892256
Glycylsarcosine,2TBDMS,isomer #2	CN(CC(=O)O)C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2205.0	Standard polar	33892256
Glycylsarcosine,3TBDMS,isomer #1	CN(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2431.1	Semi standard non polar	33892256
Glycylsarcosine,3TBDMS,isomer #1	CN(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2353.1	Standard non polar	33892256
Glycylsarcosine,3TBDMS,isomer #1	CN(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2178.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylsarcosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-9100000000-2f5d53e8d61116bdeb55	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylsarcosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylsarcosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylsarcosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylsarcosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylsarcosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Glycylsarcosine 10V, Positive-QTOF	splash10-0007-9400000000-3a75bd09f90ec5525234	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylsarcosine 20V, Positive-QTOF	splash10-007c-9000000000-719faa495e3b76ae2c85	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylsarcosine 40V, Positive-QTOF	splash10-0006-9000000000-b7d68c6a5a48e753f51a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylsarcosine 10V, Negative-QTOF	splash10-000i-9100000000-90dbb8ef290fa2f25c96	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylsarcosine 20V, Negative-QTOF	splash10-000i-9000000000-ee6b71c4cc93ab33e745	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylsarcosine 40V, Negative-QTOF	splash10-00di-9000000000-23af80e429424b839cc5	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

84077

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1914

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93131

PDB ID

Not Available

ChEBI ID

155838

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Glycylsarcosine (HMDB0252887)

MOL for HMDB0252887 (Glycylsarcosine)

3D MOL for HMDB0252887 (Glycylsarcosine)

3D SDF for HMDB0252887 (Glycylsarcosine)

3D-SDF for HMDB0252887 (Glycylsarcosine)

PDB for HMDB0252887 (Glycylsarcosine)

3D PDB for HMDB0252887 (Glycylsarcosine)

SMILES for HMDB0252887 (Glycylsarcosine)

INCHI for HMDB0252887 (Glycylsarcosine)

Structure for HMDB0252887 (Glycylsarcosine)

3D Structure for HMDB0252887 (Glycylsarcosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra