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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2016-10-26 22:29:47 UTC

Update Date

2023-02-21 17:30:39 UTC

HMDB ID

HMDB0062183

Secondary Accession Numbers

HMDB62183

Metabolite Identification

Common Name

N-lactoyl-Glycine

Description

N-lactoyl-Glycine is lactoyl derivative of glycine. N-lactoyl-amino acids are ubiquitous pseudodipeptides of lactic acid and amino acids that are rapidly formed by reverse proteolysis. A protease, cytosolic nonspecific dipeptidase 2 (CNDP2), catalyzes their formation. The plasma levels of these metabolites strongly correlate with plasma levels of lactate and amino acid. (PMID: 25964343 )

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.13

Monoisotopic Molecular Weight

147.053157774

IUPAC Name

2-[(2S)-2-hydroxypropanamido]acetic acid

Traditional Name

[(2S)-2-hydroxypropanamido]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@H](O)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C5H9NO4/c1-3(7)5(10)6-2-4(8)9/h3,7H,2H2,1H3,(H,6,10)(H,8,9)/t3-/m0/s1

InChI Key

CLNVOWMDSFOIPV-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0062183)

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	-1.2	ALOGPS
logP	-1.6	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.64 m³·mol⁻¹	ChemAxon
Polarizability	13.36 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]+	130.539	30932474
DeepCCS	[M-H]-	126.712	30932474
DeepCCS	[M-2H]-	164.056	30932474
DeepCCS	[M+Na]+	139.595	30932474
AllCCS	[M+H]+	133.5	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	127.4	32859911
AllCCS	[M+Na-2H]-	129.7	32859911
AllCCS	[M+HCOO]-	132.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.48 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2087 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	835.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	309.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	62.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	247.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	279.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	384.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	593.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	93.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	859.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	569.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	286.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	227.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-lactoyl-Glycine	C[C@H](O)C(=O)NCC(O)=O	2658.4	Standard polar	33892256
N-lactoyl-Glycine	C[C@H](O)C(=O)NCC(O)=O	1252.7	Standard non polar	33892256
N-lactoyl-Glycine	C[C@H](O)C(=O)NCC(O)=O	1474.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-lactoyl-Glycine,1TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)NCC(=O)O	1442.5	Semi standard non polar	33892256
N-lactoyl-Glycine,1TMS,isomer #2	C[C@H](O)C(=O)NCC(=O)O[Si](C)(C)C	1449.1	Semi standard non polar	33892256
N-lactoyl-Glycine,1TMS,isomer #3	C[C@H](O)C(=O)N(CC(=O)O)[Si](C)(C)C	1462.4	Semi standard non polar	33892256
N-lactoyl-Glycine,2TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)NCC(=O)O[Si](C)(C)C	1569.2	Semi standard non polar	33892256
N-lactoyl-Glycine,2TMS,isomer #2	C[C@H](O[Si](C)(C)C)C(=O)N(CC(=O)O)[Si](C)(C)C	1540.6	Semi standard non polar	33892256
N-lactoyl-Glycine,2TMS,isomer #3	C[C@H](O)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1503.7	Semi standard non polar	33892256
N-lactoyl-Glycine,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1594.0	Semi standard non polar	33892256
N-lactoyl-Glycine,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1586.2	Standard non polar	33892256
N-lactoyl-Glycine,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1627.3	Standard polar	33892256
N-lactoyl-Glycine,1TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)NCC(=O)O	1715.4	Semi standard non polar	33892256
N-lactoyl-Glycine,1TBDMS,isomer #2	C[C@H](O)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	1694.5	Semi standard non polar	33892256
N-lactoyl-Glycine,1TBDMS,isomer #3	C[C@H](O)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	1695.2	Semi standard non polar	33892256
N-lactoyl-Glycine,2TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	2009.3	Semi standard non polar	33892256
N-lactoyl-Glycine,2TBDMS,isomer #2	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	2010.0	Semi standard non polar	33892256
N-lactoyl-Glycine,2TBDMS,isomer #3	C[C@H](O)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1954.7	Semi standard non polar	33892256
N-lactoyl-Glycine,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2248.8	Semi standard non polar	33892256
N-lactoyl-Glycine,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2215.2	Standard non polar	33892256
N-lactoyl-Glycine,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2075.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-lactoyl-Glycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i4-9100000000-ea76ba47d17df2c7b449	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-lactoyl-Glycine GC-MS (2 TMS) - 70eV, Positive	splash10-0100-7930000000-61b7745d92207506b58c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-lactoyl-Glycine 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 - N-lactoyl-Glycine 10V, Positive-QTOF	splash10-0002-5900000000-1644ef91ea0788ece9c2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 20V, Positive-QTOF	splash10-0pdj-9300000000-ed7d1afe81f0bc3a857b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 40V, Positive-QTOF	splash10-056r-9000000000-0b1f74ec0daffe39f94e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 10V, Negative-QTOF	splash10-0002-1900000000-6910c2a980b3497f28ac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 20V, Negative-QTOF	splash10-00di-9600000000-67da4c7f3eb09193c6ae	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 40V, Negative-QTOF	splash10-05fr-9000000000-754a3eeb99e9f4ac11cc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 10V, Positive-QTOF	splash10-0002-9600000000-a6c5090e3bc26c8dc915	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 20V, Positive-QTOF	splash10-0002-9100000000-c014bd996f0116b0b82b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 40V, Positive-QTOF	splash10-052b-9000000000-887ab88c9fde19e0d5ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 10V, Negative-QTOF	splash10-0udj-3900000000-d1867180e593783991f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 20V, Negative-QTOF	splash10-0f7o-9200000000-898586f858cd9a84cda9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-lactoyl-Glycine 40V, Negative-QTOF	splash10-006y-9000000000-8054710154d665e8cc6e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101947384

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

Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]

Showing metabocard for N-lactoyl-Glycine (HMDB0062183)

MOL for HMDB0062183 (N-lactoyl-Glycine)

3D MOL for HMDB0062183 (N-lactoyl-Glycine)

3D SDF for HMDB0062183 (N-lactoyl-Glycine)

3D-SDF for HMDB0062183 (N-lactoyl-Glycine)

PDB for HMDB0062183 (N-lactoyl-Glycine)

3D PDB for HMDB0062183 (N-lactoyl-Glycine)

SMILES for HMDB0062183 (N-lactoyl-Glycine)

INCHI for HMDB0062183 (N-lactoyl-Glycine)

Structure for HMDB0062183 (N-lactoyl-Glycine)

3D Structure for HMDB0062183 (N-lactoyl-Glycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra