MiMeDB: Showing metabocard for Hydroxyacetone (MMDBc0048999)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:17:41 UTC

Update Date

2024-09-29 07:17:17 UTC

Metabolite ID

MMDBc0048999

Metabolite Identification

Common Name

Hydroxyacetone

Description

Hydroxyacetone, also known as acetol or acetone alcohol, belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group. Hydroxyacetone exists in all living organisms, ranging from bacteria to humans. Hydroxyacetone is a sweet, caramel, and ethereal tasting compound. hydroxyacetone has been detected, but not quantified in several different foods, such as bog bilberries, cardoons, amaranths, black salsifies, and komatsuna. This could make hydroxyacetone a potential biomarker for the consumption of these foods. Hydroxyacetone is an intermediate in glycine, serine, and threonine metabolism.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-2-propanone	ChEBI
2-Ketopropyl alcohol	ChEBI
Acetol	ChEBI
Acetone alcohol	ChEBI
Methylketol	ChEBI
Pyruvic alcohol	ChEBI
Pyruvinalcohol	ChEBI
1-Hydroxy-2-acetone	HMDB
1-Hydroxyacetone	HMDB
2-Oxopropanol	HMDB
Acetylcarbinol	HMDB
Acetylmethanol	HMDB
Hydroxymethyl methyl ketone	HMDB
Hydroxypropanone	HMDB
alpha-Hydroxyacetone	HMDB
Α-hydroxyacetone	HMDB
Hydroxyacetone	HMDB

Molecular Formula

C₃H₆O₂

Average Mass

74.0785

Monoisotopic Mass

74.036779436

IUPAC Name

1-hydroxypropan-2-one

Traditional Name

acetone alcohol

CAS Registry Number

116-09-6

SMILES

CC(=O)CO

InChI Identifier

InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3

InChI Key

XLSMFKSTNGKWQX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydroxy ketones

Alternative Parents

Substituents

Alpha-hydroxy ketone
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:27957 )
methyl ketone (CHEBI:27957 )
propanone (CHEBI:27957 )
a small molecule (ACETOL )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	680 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.71	ChemAxon
logS	0.96	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	-3.3	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	17.9 m³·mol⁻¹	ChemAxon
Polarizability	7.26 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
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-07305dfad59d2227ffa7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-2534cfaae5c1ba708730	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-017j-0930000000-279a3f07932eb1839074	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-017j-0920000000-f1af25b38da545edc6c5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-2950000000-31f525aaa70eed911510	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01rb-2900000000-bbb084ba481440566b91	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-2950000000-b22d81e8da17e3f02d19	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-07305dfad59d2227ffa7	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-2534cfaae5c1ba708730	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-017j-0930000000-279a3f07932eb1839074	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-017j-0920000000-f1af25b38da545edc6c5	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-2950000000-31f525aaa70eed911510	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01rb-2900000000-bbb084ba481440566b91	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-2950000000-b22d81e8da17e3f02d19	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5e6801cf968784a5b9de	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gi-9300000000-e781920c2fc8ee89a28a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-00di-9000000000-2d613d85b2a9ab4b81c4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-00di-9000000000-8aac708a68b987439cae	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-00di-9000000000-7aa091c76f3b2e3533f6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-00di-9000000000-a96f1f74ed0a81fc555b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-05fr-9000000000-9e9863e2481fe663a1c2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0ab9-9000000000-24d5b9ab081d2ab1dc4e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-0a4i-9000000000-bf699c4edab22a9c3392	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-0a4i-9000000000-06ca82c23199feec7913	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 11V, positive	splash10-0a4i-9000000000-6063e22276e13798069c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0a4i-9000000000-df73e7e99651b56301bf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 13V, positive	splash10-0a4i-9000000000-cab5dcbf47489b84ed56	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 14V, positive	splash10-0a4i-9000000000-490e579ce5b7ee61e4b6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 15V, positive	splash10-0a4i-9000000000-82946f673383e2e48eed	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0a4i-9000000000-9e922e16d939cec82078	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 17V, positive	splash10-0a4i-9000000000-e9f30d809fd20007a0d5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 18V, positive	splash10-0a6r-9000000000-5125f6367687313ab7e1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 19V, positive	splash10-0a6r-9000000000-81a018ab2528282c82bf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-0a6r-9000000000-3dd73306f979d472425e	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-535f26482c157dec5ff5	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9000000000-9f6cd14ffcf61c467363	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-4b977c4569c666841170	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-359666943b9e9621209c	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-67ac069288bf16663cf7	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-1ad0fc4aef1abc1d687f	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-35ce377642adfe80d15b	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-50a216336c293bf1b3ba	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		2015-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
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
MMDBp0193883	Retinol dehydrogenase 13	Enzyme	Q8NBN7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000211	Hydroxyacetone	BPG	cytochrome P450, family 2, subfamily E, polypeptide 1	VMH	1537826 16037240 8853285
MMDBr0000212	Acetone	Hydroxyacetone	cytochrome P450, family 2, subfamily E, polypeptide 1	VMH	1537826 16037240 8853285
MMDBr0000294	BPG	Hydroxyacetone	aldo-keto reductase family 1, member A1 (aldehyde reductase)	VMH; KEGG	12071861 1537826 9823300
MMDBr0000295	Hydroxyacetone	(S)-Propane-1,2-diol	aldo-keto reductase family 1, member A1 (aldehyde reductase)	VMH	12071861 1537826 9823300

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
Bacteria	Proteobacteria	4	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Actinobacteria	2	Human
Bacteria	Cyanobacteria	1
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						HMDB
Human Urine	Detected and Quantified	3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified			Newborn (0-30 days old)	Both	Normal	HMDB	21386183

External Links

HMDB ID

HMDB0006961

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hydroxyacetone

METLIN ID

Not Available

PubChem Compound

8299

PDB ID

Not Available

ChEBI ID

27957

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kelley JJ, Dekker EE: D-1-amino-2-propanol:NAD+ oxidoreductase. Purification and general properties of the large molecular form of the enzyme from Escherichia coli K12. J Biol Chem. 1984 Feb 25;259(4):2124-9. [PubMed:6365902 ]
Kasai H, Nishimura S: Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 1984 Feb 24;12(4):2137-45. doi: 10.1093/nar/12.4.2137. [PubMed:6701097 ]
Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. [PubMed:6706932 ]
Yaylayan VA, Keyhani A: Origin of carbohydrate degradation products in L-Alanine/D-[(13)C]glucose model systems. J Agric Food Chem. 2000 Jun;48(6):2415-9. doi: 10.1021/jf000004n. [PubMed:10888560 ]
HUGGINS CG, MILLER ON: The quantitative determination of acetol. J Biol Chem. 1956 Aug;221(2):711-8. [PubMed:13357464 ]
SELLINGER OZ, MILLER ON: The phosphorylation of acetol. Biochim Biophys Acta. 1959 Nov;36:266-8. doi: 10.1016/0006-3002(59)90101-5. [PubMed:14444756 ]
WERLE E, STIESS P: [Quantitative determination of acetol, with special reference to its formation in alkaline sugar decomposition]. Biochem Z. 1951;321(6):485-91. [PubMed:14858384 ]
Yamada-Onodera K, Ono K, Tani Y: Purification and characterization of an enzyme that has dihydroxyacetone-reducing activity from methanol-grown Hansenula ofunaensis. J Biosci Bioeng. 1999;88(2):148-52. doi: 10.1016/s1389-1723(99)80193-5. [PubMed:16232589 ]
Hatanaka Y, Kudo T, Miyataka M, Kobayashi O, Higashihara M, Hiyama K: Asymmetric reduction of hydroxyacetone to propanediol in immobilized halotolerant microalga Dunaliella parva. J Biosci Bioeng. 1999;88(3):281-6. doi: 10.1016/s1389-1723(00)80010-9. [PubMed:16232612 ]
Ishikawa T, Aikawa T, Ohata E, Iseki T, Maeda S, Matsuo T, Fujino T, Saito S: Two-directional elaboration of hydroxyacetone under thermodynamically controlled conditions: allylation or 2-propynylation and aldol reaction. J Org Chem. 2007 Jan 19;72(2):435-41. doi: 10.1021/jo0618573. [PubMed:17221959 ]

Showing metabocard for Hydroxyacetone (MMDBc0048999)

MOL for #<Metabolite:0x00007f46d8205078>

3D MOL for #<Metabolite:0x00007f46d8205078>

3D SDF for #<Metabolite:0x00007f46d8205078>

3D-SDF for #<Metabolite:0x00007f46d8205078>

PDB for #<Metabolite:0x00007f46d8205078>

3D PDB for #<Metabolite:0x00007f46d8205078>

SMILES for #<Metabolite:0x00007f46d8205078>

INCHI for #<Metabolite:0x00007f46d8205078>

Structure for #<Metabolite:0x00007f46d8205078>

3D Structure for #<Metabolite:0x00007f46d8205078>