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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2022-03-07 03:17:34 UTC

HMDB ID

HMDB0059649

Secondary Accession Numbers

HMDB59649

Metabolite Identification

Common Name

3-Acetamidobutanal

Description

3-Acetamidobutanal belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 3-Acetamidobutanal is a strong basic compound (based on its pKa). 3-Acetamidobutanal exists in all living organisms, ranging from bacteria to humans. 3-acetamidobutanal is part of the Amine and polyamine metabolism, and Peroxisome pathways.

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-(4-Oxobutan-2-yl)ethanimidate	Generator

Chemical Formula

C₆H₁₁NO₂

Average Molecular Weight

129.157

Monoisotopic Molecular Weight

129.078978601

IUPAC Name

N-(4-oxobutan-2-yl)ethanimidic acid

Traditional Name

N-(4-oxobutan-2-yl)ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(CC=O)N=C(C)O

InChI Identifier

InChI=1S/C6H11NO2/c1-5(3-4-8)7-6(2)9/h4-5H,3H2,1-2H3,(H,7,9)

InChI Key

SOYLQPBXNGCSNB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Acetamide
Alpha-hydrogen aldehyde
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0059649)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	3.8 g/L	ALOGPS
logP	0.47	ALOGPS
logP	-0.014	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	4.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.16 m³·mol⁻¹	ChemAxon
Polarizability	13.59 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]+	129.146	31661259
DarkChem	[M-H]-	125.95	31661259
DeepCCS	[M+H]+	128.346	30932474
DeepCCS	[M-H]-	125.975	30932474
DeepCCS	[M-2H]-	162.272	30932474
DeepCCS	[M+Na]+	137.141	30932474
AllCCS	[M+H]+	131.8	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.7	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	132.3	32859911
AllCCS	[M+HCOO]-	135.4	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.	1.95 minutes	32390414
Predicted by Siyang on May 30, 2022	8.5596 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	791.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	290.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	90.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	245.6 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	295.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	608.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	149.7 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	619.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	441.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	245.6 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	120.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Acetamidobutanal	CC(CC=O)N=C(C)O	2033.7	Standard polar	33892256
3-Acetamidobutanal	CC(CC=O)N=C(C)O	1117.4	Standard non polar	33892256
3-Acetamidobutanal	CC(CC=O)N=C(C)O	1120.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Acetamidobutanal,1TMS,isomer #1	CC(=NC(C)CC=O)O[Si](C)(C)C	1198.8	Semi standard non polar	33892256
3-Acetamidobutanal,1TMS,isomer #2	CC(O)=NC(C)C=CO[Si](C)(C)C	1324.3	Semi standard non polar	33892256
3-Acetamidobutanal,2TMS,isomer #1	CC(=NC(C)C=CO[Si](C)(C)C)O[Si](C)(C)C	1394.7	Semi standard non polar	33892256
3-Acetamidobutanal,2TMS,isomer #1	CC(=NC(C)C=CO[Si](C)(C)C)O[Si](C)(C)C	1349.2	Standard non polar	33892256
3-Acetamidobutanal,2TMS,isomer #1	CC(=NC(C)C=CO[Si](C)(C)C)O[Si](C)(C)C	1545.9	Standard polar	33892256
3-Acetamidobutanal,1TBDMS,isomer #1	CC(=NC(C)CC=O)O[Si](C)(C)C(C)(C)C	1421.8	Semi standard non polar	33892256
3-Acetamidobutanal,1TBDMS,isomer #2	CC(O)=NC(C)C=CO[Si](C)(C)C(C)(C)C	1530.1	Semi standard non polar	33892256
3-Acetamidobutanal,2TBDMS,isomer #1	CC(=NC(C)C=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1782.1	Semi standard non polar	33892256
3-Acetamidobutanal,2TBDMS,isomer #1	CC(=NC(C)C=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1781.2	Standard non polar	33892256
3-Acetamidobutanal,2TBDMS,isomer #1	CC(=NC(C)C=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1798.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetamidobutanal GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9100000000-9420facdeb138a48abaf	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetamidobutanal GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9300000000-f0346dbd5b5d0dbf61d7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetamidobutanal 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 - 3-Acetamidobutanal 10V, Positive-QTOF	splash10-001r-6900000000-2c69bdff4f5696d8579e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 20V, Positive-QTOF	splash10-01w0-9200000000-f1eabde5ee869b39c126	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 40V, Positive-QTOF	splash10-00kf-9000000000-746f9d91db0f675bbf54	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 10V, Negative-QTOF	splash10-004i-2900000000-f1581fd2f37b03bba08d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 20V, Negative-QTOF	splash10-002r-9400000000-56b0e71544b758e0c668	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 40V, Negative-QTOF	splash10-0006-9000000000-9020db7589b9a18dc9de	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 10V, Positive-QTOF	splash10-000i-9300000000-9126db9ba66cf52f1901	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 20V, Positive-QTOF	splash10-0006-9000000000-4c2cb4a90f8130041939	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 40V, Positive-QTOF	splash10-0006-9000000000-43fb489095944eaac81e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 10V, Negative-QTOF	splash10-005i-9400000000-c7981635bc3ceaf3ee02	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 20V, Negative-QTOF	splash10-0a59-9100000000-a03a1385af1f65701852	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetamidobutanal 40V, Negative-QTOF	splash10-0006-9000000000-36fceba017cd79d56609	2021-09-24	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

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

21393674

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

Not Available

Enzymes

Enzyme Details

1. Peroxisomal N(1)-acetyl-spermine/spermidine oxidase

General function:: Amino acid transport and metabolism
Specific function:: Flavoenzyme which catalyzes the oxidation of N(1)-acetylspermine to spermidine and is thus involved in the polyamine back-conversion. Can also oxidize N(1)-acetylspermidine to putrescine. Substrate specificity: N(1)-acetylspermine = N(1)-acetylspermidine > N(1),N(12)-diacylspermine >> spermine. Does not oxidize spermidine. Plays an important role in the regulation of polyamine intracellular concentration and has the potential to act as a determinant of cellular sensitivity to the antitumor polyamine analogs.
Gene Name:: PAOX
Uniprot ID:: Q6QHF9
Molecular weight:: 55512.64

Reactions

N1,N12-Diacetylspermine + Oxygen + Water → N1-Acetylspermidine + 3-Acetamidobutanal + Hydrogen peroxide	details

Showing metabocard for 3-Acetamidobutanal (HMDB0059649)

MOL for HMDB0059649 (3-Acetamidobutanal)

3D MOL for HMDB0059649 (3-Acetamidobutanal)

3D SDF for HMDB0059649 (3-Acetamidobutanal)

3D-SDF for HMDB0059649 (3-Acetamidobutanal)

PDB for HMDB0059649 (3-Acetamidobutanal)

3D PDB for HMDB0059649 (3-Acetamidobutanal)

SMILES for HMDB0059649 (3-Acetamidobutanal)

INCHI for HMDB0059649 (3-Acetamidobutanal)

Structure for HMDB0059649 (3-Acetamidobutanal)

3D Structure for HMDB0059649 (3-Acetamidobutanal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions