Cannabis Compound Database: Showing Compound Card for Hydroxyacetone (CDB004989)

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Record Information

Version

1.0

Created at

2020-04-17 18:57:49 UTC

Updated at

2020-11-18 16:39:10 UTC

CannabisDB ID

CDB004989

Secondary Accession Numbers

Not Available

Cannabis Compound 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. A propanone that is acetone in which one of the methyl hydrogens is replaced by a hydroxy group. Hydroxyacetone is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxyacetone exists in all living organisms, ranging from bacteria to humans. Hydroxyacetone is a sweet, caramellic, and ethereal tasting compound. Outside of the human body, Hydroxyacetone is found, on average, in the highest concentration within corns. Hydroxyacetone has also been detected, but not quantified in, several different foods, such as black cabbages, pulses, mentha, onion-family vegetables, and rapes. This could make hydroxyacetone a potential biomarker for the consumption of these foods. Hydroxyacetone is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Chemical Formula

C₃H₆O₂

Average Molecular Weight

74.08

Monoisotopic Molecular Weight

74.0368

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant:

Animal

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-17 °C	Not Available
Boiling Point	145–146 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-50a216336c293bf1b3ba	2015-03-01	View Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-07305dfad59d2227ffa7	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-2534cfaae5c1ba708730	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-017j-0930000000-279a3f07932eb1839074	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-017j-0920000000-f1af25b38da545edc6c5	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-014i-2950000000-31f525aaa70eed911510	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-01rb-2900000000-bbb084ba481440566b91	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-014i-2950000000-b22d81e8da17e3f02d19	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-07305dfad59d2227ffa7	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-2534cfaae5c1ba708730	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-017j-0930000000-279a3f07932eb1839074	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-017j-0920000000-f1af25b38da545edc6c5	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-014i-2950000000-31f525aaa70eed911510	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-01rb-2900000000-bbb084ba481440566b91	Spectrum
GC-MS	Hydroxyacetone, non-derivatized, GC-MS Spectrum	splash10-014i-2950000000-b22d81e8da17e3f02d19	Spectrum
Predicted GC-MS	Hydroxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-5e6801cf968784a5b9de	Spectrum
Predicted GC-MS	Hydroxyacetone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gi-9300000000-e781920c2fc8ee89a28a	Spectrum
Predicted GC-MS	Hydroxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-00di-9000000000-2d613d85b2a9ab4b81c4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-00di-9000000000-8aac708a68b987439cae	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-00di-9000000000-7aa091c76f3b2e3533f6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-00di-9000000000-a96f1f74ed0a81fc555b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-05fr-9000000000-9e9863e2481fe663a1c2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0ab9-9000000000-24d5b9ab081d2ab1dc4e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-0a4i-9000000000-bf699c4edab22a9c3392	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-0a4i-9000000000-06ca82c23199feec7913	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 11V, positive	splash10-0a4i-9000000000-6063e22276e13798069c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0a4i-9000000000-df73e7e99651b56301bf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 13V, positive	splash10-0a4i-9000000000-cab5dcbf47489b84ed56	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 14V, positive	splash10-0a4i-9000000000-490e579ce5b7ee61e4b6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 15V, positive	splash10-0a4i-9000000000-82946f673383e2e48eed	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0a4i-9000000000-9e922e16d939cec82078	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 17V, positive	splash10-0a4i-9000000000-e9f30d809fd20007a0d5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 18V, positive	splash10-0a6r-9000000000-5125f6367687313ab7e1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 19V, positive	splash10-0a6r-9000000000-81a018ab2528282c82bf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-0a6r-9000000000-3dd73306f979d472425e	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-535f26482c157dec5ff5	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9000000000-9f6cd14ffcf61c467363	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-4b977c4569c666841170	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-359666943b9e9621209c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-67ac069288bf16663cf7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-1ad0fc4aef1abc1d687f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-35ce377642adfe80d15b	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Retinol dehydrogenase 13	RDH13	19q13.42	Q8NBN7	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0006961

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

General References

Not Available

Enzymes

Enzyme Details

1. Retinol dehydrogenase 13

General function:: Involved in oxidoreductase activity
Specific function:: Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:: RDH13
Uniprot ID:: Q8NBN7
Molecular weight:: 35931.8

Showing Compound Card for Hydroxyacetone (CDB004989)

Structure for CDB004989 (Hydroxyacetone)

Enzymes