MiMeDB: Showing metabocard for 3-Hydroxy-3-methyl-2-butanone (MMDBc0017342)

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:45:06 UTC

Update Date

2025-10-07 16:06:40 UTC

Metabolite ID

MMDBc0017342

Metabolite Identification

Common Name

3-Hydroxy-3-methyl-2-butanone

Description

3-Hydroxy-3-methyl-2-butanone is a ketone and an alpha-hydroxy ketone, classified as a metabolite in various biochemical pathways. Its chemical structure consists of a five-carbon backbone with a hydroxyl group and a methyl group at the third carbon, contributing to its reactivity. This compound has been studied for its interactions with hydroxyl (OH) radicals and chlorine (Cl) atoms in atmospheric chemistry, indicating its role in tropospheric reactions and potential implications for air quality. For instance, the kinetics of the reaction of OH radicals with 3-hydroxy-3-methyl-2-butanone were investigated over a wide temperature range, revealing important insights into its behavior under varying atmospheric conditions (PMID:31668071 ). Additionally, the relative rate coefficient for its gas-phase reaction with Cl atoms was determined, highlighting its significance in atmospheric chemistry (PMID:25069003 ). The compound also participates in organic reactions, forming stable adducts with various cations (PMID:11857760 ). Furthermore, it has been noted in biochemical tests related to acetoin, where it showed distinct reactivity patterns compared to other related compounds (PMID:6751225 ). Overall, 3-hydroxy-3-methyl-2-butanone serves as a key player in both chemical and biological contexts.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₅H₁₀O₂

Average Mass

102.133

Monoisotopic Mass

102.068079562

IUPAC Name

3-hydroxy-3-methylbutan-2-one

Traditional Name

3-hydroxy-3-methyl-2-butanone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C5H10O2/c1-4(6)5(2,3)7/h7H,1-3H3

InChI Key

BNDRWEVUODOUDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000066 )
a small molecule (CPD-10354 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	157 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	0.29	ChemAxon
logS	0.19	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.1 m³·mol⁻¹	ChemAxon
Polarizability	10.92 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	275.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	45.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	298.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	439.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	372.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	360.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	1375.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	107.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	527.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	334.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	337.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	219.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	115.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	62.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	403.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	61.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	272.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	919.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	698.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-Hydroxy-3-methyl-2-butanone_TMS_1	CC(=O)C(C)(C)O[Si](C)(C)C	standard non polar	2025-10-23	2068.11
Gas Chromatography	3-Hydroxy-3-methyl-2-butanone_TMS_2	C=C(O[Si](C)(C)C)C(C)(C)O	standard non polar	2025-10-23	1809.63
Gas Chromatography	3-Hydroxy-3-methyl-2-butanone_TMS_3	C=C(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C	standard non polar	2025-10-23	2040.74
Gas Chromatography	3-Hydroxy-3-methyl-2-butanone_TMS_1	CC(=O)C(C)(C)O[Si](C)(C)C	standard polar	2025-10-23	1946.55
Gas Chromatography	3-Hydroxy-3-methyl-2-butanone_TMS_2	C=C(O[Si](C)(C)C)C(C)(C)O	standard polar	2025-10-23	2168.39
Gas Chromatography	3-Hydroxy-3-methyl-2-butanone_TMS_3	C=C(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C	standard polar	2025-10-23	1733.45

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

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

8261

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 3-Hydroxy-3-methyl-2-butanone (MMDBc0017342)

MOL for #<Metabolite:0x00007f9ab2d6ebe8>

3D MOL for #<Metabolite:0x00007f9ab2d6ebe8>

3D SDF for #<Metabolite:0x00007f9ab2d6ebe8>

3D-SDF for #<Metabolite:0x00007f9ab2d6ebe8>

PDB for #<Metabolite:0x00007f9ab2d6ebe8>

3D PDB for #<Metabolite:0x00007f9ab2d6ebe8>

SMILES for #<Metabolite:0x00007f9ab2d6ebe8>

INCHI for #<Metabolite:0x00007f9ab2d6ebe8>

Structure for #<Metabolite:0x00007f9ab2d6ebe8>

3D Structure for #<Metabolite:0x00007f9ab2d6ebe8>