Showing Compound Card for Hydroxyacetone (CDB004989)

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Record Information
Version1.0
Created at2020-04-17 18:57:49 UTC
Updated at2020-11-18 16:39:10 UTC
CannabisDB IDCDB004989
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHydroxyacetone
DescriptionHydroxyacetone, 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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Hydroxy-2-propanoneChEBI
2-Ketopropyl alcoholChEBI
AcetolChEBI
Acetone alcoholChEBI
MethylketolChEBI
Pyruvic alcoholChEBI
PyruvinalcoholChEBI
1-Hydroxy-2-acetoneHMDB
1-HydroxyacetoneHMDB
2-OxopropanolHMDB
AcetylcarbinolHMDB
AcetylmethanolHMDB
Hydroxymethyl methyl ketoneHMDB
HydroxypropanoneHMDB
alpha-HydroxyacetoneHMDB
Α-hydroxyacetoneHMDB
HydroxyacetoneHMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.08
Monoisotopic Molecular Weight74.0368
IUPAC Name1-hydroxypropan-2-one
Traditional Nameacetone alcohol
CAS Registry Number116-09-6
SMILES
CC(=O)CO
InChI Identifier
InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
InChI KeyXLSMFKSTNGKWQX-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydroxy ketones
Alternative Parents
Substituents
  • Alpha-hydroxy ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-17 °CNot Available
Boiling Point145–146 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP-0.71ChemAxon
logS0.96ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.9 m³·mol⁻¹ChemAxon
Polarizability7.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-50a216336c293bf1b3ba2015-03-01View Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-07305dfad59d2227ffa7Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-2534cfaae5c1ba708730Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-017j-0930000000-279a3f07932eb1839074Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-017j-0920000000-f1af25b38da545edc6c5Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-014i-2950000000-31f525aaa70eed911510Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-01rb-2900000000-bbb084ba481440566b91Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-014i-2950000000-b22d81e8da17e3f02d19Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-07305dfad59d2227ffa7Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-2534cfaae5c1ba708730Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-017j-0930000000-279a3f07932eb1839074Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-017j-0920000000-f1af25b38da545edc6c5Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-014i-2950000000-31f525aaa70eed911510Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-01rb-2900000000-bbb084ba481440566b91Spectrum
GC-MSHydroxyacetone, non-derivatized, GC-MS Spectrumsplash10-014i-2950000000-b22d81e8da17e3f02d19Spectrum
Predicted GC-MSHydroxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-5e6801cf968784a5b9deSpectrum
Predicted GC-MSHydroxyacetone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gi-9300000000-e781920c2fc8ee89a28aSpectrum
Predicted GC-MSHydroxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-00di-9000000000-2d613d85b2a9ab4b81c42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-00di-9000000000-8aac708a68b987439cae2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-00di-9000000000-7aa091c76f3b2e3533f62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-00di-9000000000-a96f1f74ed0a81fc555b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-05fr-9000000000-9e9863e2481fe663a1c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0ab9-9000000000-24d5b9ab081d2ab1dc4e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0a4i-9000000000-bf699c4edab22a9c33922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0a4i-9000000000-06ca82c23199feec79132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-0a4i-9000000000-6063e22276e13798069c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-df73e7e99651b56301bf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 13V, positivesplash10-0a4i-9000000000-cab5dcbf47489b84ed562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-0a4i-9000000000-490e579ce5b7ee61e4b62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 15V, positivesplash10-0a4i-9000000000-82946f673383e2e48eed2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-9e922e16d939cec820782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 17V, positivesplash10-0a4i-9000000000-e9f30d809fd20007a0d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-0a6r-9000000000-5125f6367687313ab7e12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 19V, positivesplash10-0a6r-9000000000-81a018ab2528282c82bf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-0a6r-9000000000-3dd73306f979d472425e2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-535f26482c157dec5ff52015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-9f6cd14ffcf61c4673632015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-4b977c4569c6668411702015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-359666943b9e9621209c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-67ac069288bf16663cf72015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ad0fc4aef1abc1d687f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-35ce377642adfe80d15b2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Retinol dehydrogenase 13RDH1319q13.42Q8NBN7 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006961
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012041
KNApSAcK IDC00019558
Chemspider ID21106125
KEGG Compound IDC05235
BioCyc IDACETOL
BiGG IDNot Available
Wikipedia LinkHydroxyacetone
METLIN IDNot Available
PubChem Compound8299
PDB IDNot Available
ChEBI ID27957
References
General ReferencesNot 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