MiMeDB: Showing metabocard for Acetoin (MMDBc0000230)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:40:37 UTC

Update Date

2024-10-06 23:49:45 UTC

Metabolite ID

MMDBc0000230

Metabolite Identification

Common Name

Acetoin

Description

Acetoin is a product of fermentation. It is a component of the butanediol cycle in microorganisms. In mammals it is oxidized to carbon dioxide. -- Pubchem; '3-Hydroxybutanone, also known as acetoin or acetyl methyl carbinol, is a chemical compound composed of carbon, hydrogen and oxygen. Its formula is C4H8O2. It is a colourless or pale yellow to green yellow liquid with a pleasant buttery odour. It is used as a food flavoring and a fragrance. -- Wikipedia .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Acetoin	ChEBI
1-Hydroxyethyl methyl ketone	ChEBI
2,3-Butanolone	ChEBI
2-Acetoin	ChEBI
2-Hydroxy-3-butanone	ChEBI
3-Hydroxy-2-butanone	ChEBI
3-Hydroxybutan-2-one	ChEBI
Acetyl methyl carbinol	ChEBI
Dimethylketol	ChEBI
gamma-Hydroxy-beta-oxobutane	ChEBI
g-Hydroxy-b-oxobutane	Generator
Γ-hydroxy-β-oxobutane	Generator
3H-2b Butanone	MeSH
Acetylmethylcarbinol	MeSH
(R)-2-Acetoin	HMDB
(R)-3-Hydroxy-2-butanone	HMDB
(R)-3-Hydroxybutan-2-one	HMDB
(R)-Acetoin	HMDB
(R)-Dimethylketol	HMDB
2-Butanol-3-one	HMDB
2-Hydroxy-3-oxobutane	HMDB
3-Hydroxyl-2-butanone	HMDB
Acetoine	HMDB
b-Oxobutane	HMDB
beta-Oxobutane	HMDB
Acetoin	MeSH

Molecular Formula

C₄H₈O₂

Average Mass

88.1051

Monoisotopic Mass

88.0524295

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

513-86-0

SMILES

Not Available

InChI Identifier

InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3

InChI Key

ROWKJAVDOGWPAT-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
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl ketone (CHEBI:15688 )
Oxygenated hydrocarbons (LMFA12000020 )
acetoin (CPD-255 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Urine

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

Metabolic Reactions

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
Celiac disease	Slight Increase	Association	Human Feces	HMDB	21970810
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	12	Human ; Human supragingival plaque; Human saliva; Human subgingival plaque; Human feces; Human mucosa	Microbial culture
Bacteria	Bacteroidetes	3	Human	Microbial culture
Bacteria	Spirochaetes	1		Microbial culture
Bacteria	Proteobacteria	2		Microbial culture
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Coffee	Coffea canephora	FooDB	DFC codes
Food			FooDB	D. KOMES et al. Study of phenolic and volatile composition of white wine during fermentation. Vitis 46 (2), 77-84 (2007)
Food			FooDB	Tressl R., Friese L., Fendesack F., K√∂ppler H. Gas chromatographic-mass spectrometric investigation of hop aroma constituents in beer. J. agric. Food Chem. 1978;26:1422-1426
Food			FooDB	26083035
Food	Coffee	Coffea arabica	FooDB	DFC codes
Food			FooDB	16535224
Food			FooDB	16535224
Plant			FooDB	DFC codes
Plant	Juice	Rubus	FooDB	Dimitris N. Georgilopoulos and Annie N. Gallois. Aroma compounds of fresh blackberries (Rubus laciniata L.) Zeitschrift f√É∆í√Ü‚Äô√É‚Äö√Ç¬ºr Lebensmittel-Untersuchung und Forschung, 1987, 184(5), 374-380. https://link.springer.com/content/pdf/10.1007/BF01126660.pdf
Plant	Endosperm	Cocos nucifera	FooDB	DUKE
Plant	Leaves		FooDB	DUKE
Plant	Leaves		FooDB	DUKE
Plant	Fruit juice	Vaccinium myrtillus	FooDB	DUKE
Plant		Allium cepa	FooDB	DFC codes
Plant	Juice	Rubus	FooDB	Hans-Ulrich Humpf and Peter Schreier. Bound aroma compounds from the fruit and the leaves of blackberry (Rubus laciniata L.) J. Agrie. FoodChem. 1991, 39. 1830-1832 https://pubs.acs.org/doi/pdf/10.1021/jf00010a028
Plant	Leaves		FooDB	DUKE
Plant		Allium fistulosum	FooDB	DFC codes
Plant	Root	Daucus carota ssp. sativus	FooDB	676525
Plant	Fruit	Vaccinium myrtillus	FooDB	Timo Hirvi and Erkki Honkanen. The arome of blueberries. J. Sci. Food Agric. 1983, 34, 992-998. DOI: 10.1002/jsfa.2740340916
Plant	Flower	Helianthus annuus	FooDB	DUKE
Plant		Theobroma cacao	FooDB	DFC codes
Plant	Fruit	Ficus carica	FooDB	DUKE
Plant	Essential oil	Mentha spicata	FooDB	DUKE
Plant	Fruit	Rubus	FooDB	Dimitris N. Georgilopoulos and Annie N. Gallois. Volatile flavour compounds in heated blackberry juices. Z LebensmUnters Forsch (1987) 185:299-306
Plant	Leaves	Camellia sinensis	FooDB	DUKE
Plant	Fruit	Rubus idaeus	FooDB	DUKE
Plant	Fruit	Capsicum annuum	FooDB	DUKE

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	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
Human Feces	Detected and Quantified			0	3877982.0918	nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	HMDB	21970810
Human Feces	Detected and Quantified	11.35				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	41.617				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified	56.75				nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	HMDB	26416813
Human Feces	Detected and Quantified			0	478519.405	nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Urine	Detected and Quantified	5.516	5.604			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	2.497	2.989			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	1.06	1.54			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090

External Links

HMDB ID

HMDB0003243

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetoin

METLIN ID

103

PubChem Compound

179

PDB ID

Not Available

ChEBI ID

15688

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Otsuka M, Ohmori S: Simple and sensitive determination of diacetyl and acetoin in biological samples and alcoholic drinks by gas chromatography with electron-capture detection. J Chromatogr. 1992 Jun 10;577(2):215-20. doi: 10.1016/0378-4347(92)80242-i. [PubMed:1400754 ]
Walker V, Mills GA, Hall MA, Lowes JA: Carbohydrate fermentation by gut microflora in preterm neonates. Arch Dis Child. 1989 Oct;64(10 Spec No):1367-73. doi: 10.1136/adc.64.10_spec_no.1367. [PubMed:2589871 ]
Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. [PubMed:2758593 ]
Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. doi: 10.1016/0168-1605(88)90036-0. [PubMed:3275321 ]

Showing metabocard for Acetoin (MMDBc0000230)

MOL for #<Metabolite:0x00007fdaf0890710>

3D MOL for #<Metabolite:0x00007fdaf0890710>

3D SDF for #<Metabolite:0x00007fdaf0890710>

3D-SDF for #<Metabolite:0x00007fdaf0890710>

PDB for #<Metabolite:0x00007fdaf0890710>

3D PDB for #<Metabolite:0x00007fdaf0890710>

SMILES for #<Metabolite:0x00007fdaf0890710>

INCHI for #<Metabolite:0x00007fdaf0890710>

Structure for #<Metabolite:0x00007fdaf0890710>

3D Structure for #<Metabolite:0x00007fdaf0890710>