Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:33:05 UTC

Update Date

2021-09-26 23:09:30 UTC

HMDB ID

HMDB0255023

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-(Hydroxymethyl)acrylamide

Description

N-(HYDROXYMETHYL)ACRYLAMIDE, also known as N-MAM or N-hydroxymethylacrylamide, belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof. Based on a literature review a significant number of articles have been published on N-(HYDROXYMETHYL)ACRYLAMIDE. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-(hydroxymethyl)acrylamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-(Hydroxymethyl)acrylamide 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
N-MAM	MeSH
N-Hydroxymethylacrylamide	MeSH
N-Methanolacrylamide	MeSH
N-Methylolacrylamide	MeSH
Monomethylolacrylamide	MeSH
N-(Hydroxymethyl)acrylamide	KEGG
N-(Hydroxymethyl)prop-2-enimidate	Generator

Chemical Formula

C₄H₇NO₂

Average Molecular Weight

101.105

Monoisotopic Molecular Weight

101.047678469

IUPAC Name

N-(hydroxymethyl)prop-2-enimidic acid

Traditional Name

N-(hydroxymethyl)prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

OCN=C(O)C=C

InChI Identifier

InChI=1S/C4H7NO2/c1-2-4(7)5-3-6/h2,6H,1,3H2,(H,5,7)

InChI Key

CNCOEDDPFOAUMB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Acrylic acids and derivatives

Direct Parent

Acrylic acids and derivatives

Alternative Parents

Substituents

Acrylic acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxamide (CHEBI:82492 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	-0.33	ALOGPS
logP	0.19	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	1.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.63 m³·mol⁻¹	ChemAxon
Polarizability	9.99 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]+	121.965	30932474
DeepCCS	[M-H]-	119.415	30932474
DeepCCS	[M-2H]-	155.575	30932474
DeepCCS	[M+Na]+	130.17	30932474
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	130.4	32859911
AllCCS	[M+Na]+	131.6	32859911
AllCCS	[M-H]-	124.0	32859911
AllCCS	[M+Na-2H]-	127.9	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(Hydroxymethyl)acrylamide	OCN=C(O)C=C	2086.0	Standard polar	33892256
N-(Hydroxymethyl)acrylamide	OCN=C(O)C=C	1106.5	Standard non polar	33892256
N-(Hydroxymethyl)acrylamide	OCN=C(O)C=C	1096.2	Semi 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-(Hydroxymethyl)acrylamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-a4ac7e847927cae753ec	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(Hydroxymethyl)acrylamide GC-MS (TBDMS_2_1) - 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 - N-(Hydroxymethyl)acrylamide 10V, Negative-QTOF	splash10-0uk9-9400000000-d9c9a5e4880b2bf5d6f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Hydroxymethyl)acrylamide 20V, Negative-QTOF	splash10-0fk9-9000000000-fb69058fee15e347cd94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Hydroxymethyl)acrylamide 40V, Negative-QTOF	splash10-0f96-9000000000-6b03d87954c4b7025d51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Hydroxymethyl)acrylamide 10V, Positive-QTOF	splash10-0uk9-9300000000-15ce3011f3d62541bb36	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Hydroxymethyl)acrylamide 20V, Positive-QTOF	splash10-0002-9000000000-75e6466b227b15bd3534	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(Hydroxymethyl)acrylamide 40V, Positive-QTOF	splash10-0zi1-9000000000-fe3918bcb578a3d0b2dd	2016-06-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

12955

KEGG Compound ID

C19456

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13543

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1264911

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 N-(Hydroxymethyl)acrylamide (HMDB0255023)

MOL for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

3D MOL for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

3D SDF for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

3D-SDF for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

PDB for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

3D PDB for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

SMILES for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

INCHI for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

Structure for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

3D Structure for HMDB0255023 (N-(Hydroxymethyl)acrylamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra