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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:21 UTC

Update Date

2023-02-21 17:21:59 UTC

HMDB ID

HMDB0032356

Secondary Accession Numbers

HMDB32356

Metabolite Identification

Common Name

N-Lactoyl ethanolamine

Description

N-Lactoyl ethanolamine belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. Based on a literature review very few articles have been published on N-Lactoyl ethanolamine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-Propanamide, 2-hydroxy-N-(2-hydroxyethyl)	HMDB
Lactic acid monoethanolamide	HMDB
N-(2-Hydroxyethyl)-lactamide	HMDB
N-(2-Hydroxyethyl)lactamide	HMDB
N-(beta-Hydroxyethyl)-2-hydroxypropionamide	HMDB
1-Hydroxyethane-1-(2'- hydroxyethyl)carbonamide	HMDB
2-Hydroxy-N-(2-hydroxyethyl)propanimidate	HMDB

Chemical Formula

C₅H₁₁NO₃

Average Molecular Weight

133.1457

Monoisotopic Molecular Weight

133.073893223

IUPAC Name

2-hydroxy-N-(2-hydroxyethyl)propanamide

Traditional Name

N-(2-hydroxyethyl)lactamide

CAS Registry Number

5422-34-4

SMILES

CC(O)C(=O)NCCO

InChI Identifier

InChI=1S/C5H11NO3/c1-4(8)5(9)6-2-3-7/h4,7-8H,2-3H2,1H3,(H,6,9)

InChI Key

RZCHTMXTKQHYDT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032356)
Cytoplasm (HMDB: HMDB0032356)

Source

Endogenous

Endogenous (HMDB: HMDB0032356)

Exogenous

Food

Food (HMDB: HMDB0032356)

Exogenous (HMDB: HMDB0032356)

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	380.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.268 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	251 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.7	ChemAxon
logS	0.27	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.85 m³·mol⁻¹	ChemAxon
Polarizability	13.43 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
DarkChem	[M+H]+	128.388	31661259
DarkChem	[M-H]-	123.595	31661259
DeepCCS	[M+H]+	129.883	30932474
DeepCCS	[M-H]-	127.401	30932474
DeepCCS	[M-2H]-	163.66	30932474
DeepCCS	[M+Na]+	138.695	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.6	32859911
AllCCS	[M+NH4]+	135.4	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	133.1	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.	1.44 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7853 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.44 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	172.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	730.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	60.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	248.0 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	243.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	484.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	569.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.4 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	815.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	532.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.0 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	209.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Lactoyl ethanolamine	CC(O)C(=O)NCCO	2422.3	Standard polar	33892256
N-Lactoyl ethanolamine	CC(O)C(=O)NCCO	1380.0	Standard non polar	33892256
N-Lactoyl ethanolamine	CC(O)C(=O)NCCO	1359.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Lactoyl ethanolamine,1TMS,isomer #1	CC(O[Si](C)(C)C)C(=O)NCCO	1378.4	Semi standard non polar	33892256
N-Lactoyl ethanolamine,1TMS,isomer #2	CC(O)C(=O)NCCO[Si](C)(C)C	1383.0	Semi standard non polar	33892256
N-Lactoyl ethanolamine,1TMS,isomer #3	CC(O)C(=O)N(CCO)[Si](C)(C)C	1367.9	Semi standard non polar	33892256
N-Lactoyl ethanolamine,2TMS,isomer #1	CC(O[Si](C)(C)C)C(=O)NCCO[Si](C)(C)C	1483.2	Semi standard non polar	33892256
N-Lactoyl ethanolamine,2TMS,isomer #2	CC(O[Si](C)(C)C)C(=O)N(CCO)[Si](C)(C)C	1429.0	Semi standard non polar	33892256
N-Lactoyl ethanolamine,2TMS,isomer #3	CC(O)C(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	1447.1	Semi standard non polar	33892256
N-Lactoyl ethanolamine,3TMS,isomer #1	CC(O[Si](C)(C)C)C(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	1520.8	Semi standard non polar	33892256
N-Lactoyl ethanolamine,3TMS,isomer #1	CC(O[Si](C)(C)C)C(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	1538.0	Standard non polar	33892256
N-Lactoyl ethanolamine,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(=O)NCCO	1623.3	Semi standard non polar	33892256
N-Lactoyl ethanolamine,1TBDMS,isomer #2	CC(O)C(=O)NCCO[Si](C)(C)C(C)(C)C	1628.8	Semi standard non polar	33892256
N-Lactoyl ethanolamine,1TBDMS,isomer #3	CC(O)C(=O)N(CCO)[Si](C)(C)C(C)(C)C	1577.8	Semi standard non polar	33892256
N-Lactoyl ethanolamine,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(=O)NCCO[Si](C)(C)C(C)(C)C	1914.9	Semi standard non polar	33892256
N-Lactoyl ethanolamine,2TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)C(=O)N(CCO)[Si](C)(C)C(C)(C)C	1870.5	Semi standard non polar	33892256
N-Lactoyl ethanolamine,2TBDMS,isomer #3	CC(O)C(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1891.8	Semi standard non polar	33892256
N-Lactoyl ethanolamine,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2176.4	Semi standard non polar	33892256
N-Lactoyl ethanolamine,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2169.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoyl ethanolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-b3dbc4aaf203efccd19d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoyl ethanolamine GC-MS (2 TMS) - 70eV, Positive	splash10-014i-2910000000-6350e631cdfd8659980b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lactoyl ethanolamine 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 ethanolamine 10V, Positive-QTOF	splash10-03di-9300000000-380099543b14a0549c9c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 20V, Positive-QTOF	splash10-03di-9100000000-916633c733bd390ae2cc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 40V, Positive-QTOF	splash10-0006-9000000000-1068a39731b50e335d3a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 10V, Negative-QTOF	splash10-001i-5900000000-2c60f4080f2559578d4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 20V, Negative-QTOF	splash10-03di-9400000000-383300519fe0c8bb1da8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 40V, Negative-QTOF	splash10-00dl-9000000000-5816421dde4ddaa12e2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 10V, Positive-QTOF	splash10-0002-9300000000-dde17f1c161ecac7a35c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 20V, Positive-QTOF	splash10-0002-9000000000-d9e9a6f50c598af91196	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 40V, Positive-QTOF	splash10-006w-9000000000-286e6b1cf70f9a225ec7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 10V, Negative-QTOF	splash10-001r-6900000000-72940009a13a655f2aa0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 20V, Negative-QTOF	splash10-0006-9000000000-caf92b1a2274ed172ea8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lactoyl ethanolamine 40V, Negative-QTOF	splash10-0006-9000000000-74421c0160e054f9c852	2021-09-23	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

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

FDB009682

KNApSAcK ID

Not Available

Chemspider ID

86153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95457

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1128381

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for N-Lactoyl ethanolamine (HMDB0032356)

MOL for HMDB0032356 (N-Lactoyl ethanolamine)

3D MOL for HMDB0032356 (N-Lactoyl ethanolamine)

3D SDF for HMDB0032356 (N-Lactoyl ethanolamine)

3D-SDF for HMDB0032356 (N-Lactoyl ethanolamine)

PDB for HMDB0032356 (N-Lactoyl ethanolamine)

3D PDB for HMDB0032356 (N-Lactoyl ethanolamine)

SMILES for HMDB0032356 (N-Lactoyl ethanolamine)

INCHI for HMDB0032356 (N-Lactoyl ethanolamine)

Structure for HMDB0032356 (N-Lactoyl ethanolamine)

3D Structure for HMDB0032356 (N-Lactoyl ethanolamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra