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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 01:03:43 UTC

Update Date

2021-09-26 22:57:51 UTC

HMDB ID

HMDB0247909

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetoacetaldehyde

Description

Acetoacetaldehyde belongs to the class of organic compounds known as beta ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the second carbon atom. Based on a literature review a small amount of articles have been published on Acetoacetaldehyde. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acetoacetaldehyde is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acetoacetaldehyde 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

Not Available

Chemical Formula

C₄H₆O₂

Average Molecular Weight

86.09

Monoisotopic Molecular Weight

86.036779433

IUPAC Name

3-oxobutanal

Traditional Name

acetoacetaldehyde

CAS Registry Number

Not Available

SMILES

CC(=O)CC=O

InChI Identifier

InChI=1S/C4H6O2/c1-4(6)2-3-5/h3H,2H2,1H3

InChI Key

PKQIDSVLSKFZQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the second carbon atom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Beta ketoaldehydes

Alternative Parents

Substituents

1,3-dicarbonyl compound
Beta-ketoaldehyde
Alpha-hydrogen aldehyde
Ketone
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
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)

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	0.01	ALOGPS
logP	-0.16	ChemAxon
logS	0.36	ALOGPS
pKa (Strongest Acidic)	7.59	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	21.61 m³·mol⁻¹	ChemAxon
Polarizability	8.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	121.03	30932474
DeepCCS	[M-H]-	118.921	30932474
DeepCCS	[M-2H]-	154.754	30932474
DeepCCS	[M+Na]+	129.27	30932474
AllCCS	[M+H]+	122.2	32859911
AllCCS	[M+H-H2O]+	117.8	32859911
AllCCS	[M+NH4]+	126.4	32859911
AllCCS	[M+Na]+	127.6	32859911
AllCCS	[M-H]-	125.6	32859911
AllCCS	[M+Na-2H]-	130.1	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetoacetaldehyde	CC(=O)CC=O	1275.2	Standard polar	33892256
Acetoacetaldehyde	CC(=O)CC=O	689.4	Standard non polar	33892256
Acetoacetaldehyde	CC(=O)CC=O	738.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetoacetaldehyde,1TMS,isomer #1	CC(=CC=O)O[Si](C)(C)C	1017.4	Semi standard non polar	33892256
Acetoacetaldehyde,1TMS,isomer #1	CC(=CC=O)O[Si](C)(C)C	926.7	Standard non polar	33892256
Acetoacetaldehyde,1TMS,isomer #1	CC(=CC=O)O[Si](C)(C)C	1171.5	Standard polar	33892256
Acetoacetaldehyde,1TMS,isomer #2	C=C(CC=O)O[Si](C)(C)C	960.2	Semi standard non polar	33892256
Acetoacetaldehyde,1TMS,isomer #2	C=C(CC=O)O[Si](C)(C)C	951.4	Standard non polar	33892256
Acetoacetaldehyde,1TMS,isomer #2	C=C(CC=O)O[Si](C)(C)C	1214.3	Standard polar	33892256
Acetoacetaldehyde,1TMS,isomer #3	CC(=O)C=CO[Si](C)(C)C	966.2	Semi standard non polar	33892256
Acetoacetaldehyde,1TMS,isomer #3	CC(=O)C=CO[Si](C)(C)C	886.8	Standard non polar	33892256
Acetoacetaldehyde,1TMS,isomer #3	CC(=O)C=CO[Si](C)(C)C	1217.7	Standard polar	33892256
Acetoacetaldehyde,2TMS,isomer #1	C=C(C=CO[Si](C)(C)C)O[Si](C)(C)C	1140.5	Semi standard non polar	33892256
Acetoacetaldehyde,2TMS,isomer #1	C=C(C=CO[Si](C)(C)C)O[Si](C)(C)C	1109.1	Standard non polar	33892256
Acetoacetaldehyde,2TMS,isomer #1	C=C(C=CO[Si](C)(C)C)O[Si](C)(C)C	1162.5	Standard polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #1	CC(=CC=O)O[Si](C)(C)C(C)(C)C	1253.2	Semi standard non polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #1	CC(=CC=O)O[Si](C)(C)C(C)(C)C	1152.0	Standard non polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #1	CC(=CC=O)O[Si](C)(C)C(C)(C)C	1342.9	Standard polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #2	C=C(CC=O)O[Si](C)(C)C(C)(C)C	1186.5	Semi standard non polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #2	C=C(CC=O)O[Si](C)(C)C(C)(C)C	1165.4	Standard non polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #2	C=C(CC=O)O[Si](C)(C)C(C)(C)C	1369.8	Standard polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #3	CC(=O)C=CO[Si](C)(C)C(C)(C)C	1227.0	Semi standard non polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #3	CC(=O)C=CO[Si](C)(C)C(C)(C)C	1125.3	Standard non polar	33892256
Acetoacetaldehyde,1TBDMS,isomer #3	CC(=O)C=CO[Si](C)(C)C(C)(C)C	1398.0	Standard polar	33892256
Acetoacetaldehyde,2TBDMS,isomer #1	C=C(C=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1587.8	Semi standard non polar	33892256
Acetoacetaldehyde,2TBDMS,isomer #1	C=C(C=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1540.0	Standard non polar	33892256
Acetoacetaldehyde,2TBDMS,isomer #1	C=C(C=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1461.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetoacetaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-e7ae27fc5e4d6e78c7cf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetoacetaldehyde 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 - Acetoacetaldehyde 10V, Positive-QTOF	splash10-00kf-9000000000-560766c714904726e922	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetoacetaldehyde 20V, Positive-QTOF	splash10-0006-9000000000-180bdb5f0a5e85f8ec3c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetoacetaldehyde 40V, Positive-QTOF	splash10-0006-9000000000-c4f49c1a0bdce3c3d5c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetoacetaldehyde 10V, Negative-QTOF	splash10-000i-9000000000-63a2db7b932ef2c77d1c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetoacetaldehyde 20V, Negative-QTOF	splash10-0a4i-9000000000-442d01d78fec54bfe7fb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetoacetaldehyde 40V, Negative-QTOF	splash10-0a4l-9000000000-5c675411f5cc8bb4b851	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

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

3874762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4686860

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

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 Acetoacetaldehyde (HMDB0247909)

MOL for HMDB0247909 (Acetoacetaldehyde)

3D MOL for HMDB0247909 (Acetoacetaldehyde)

3D SDF for HMDB0247909 (Acetoacetaldehyde)

3D-SDF for HMDB0247909 (Acetoacetaldehyde)

PDB for HMDB0247909 (Acetoacetaldehyde)

3D PDB for HMDB0247909 (Acetoacetaldehyde)

SMILES for HMDB0247909 (Acetoacetaldehyde)

INCHI for HMDB0247909 (Acetoacetaldehyde)

Structure for HMDB0247909 (Acetoacetaldehyde)

3D Structure for HMDB0247909 (Acetoacetaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra