NAV

(S)-acetoin

Identification

Generic Name
(S)-acetoin
DrugBank Accession Number
DB02788
Background

A product of fermentation. It is a component of the butanediol cycle in microorganisms. In mammals it is oxidized to carbon dioxide.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 88.1051
Monoisotopic: 88.0524295
Chemical Formula
C4H8O2
Synonyms
  • (S)-2-acetoin
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Alpha-hydroxy ketones / Secondary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Acyloin / Alcohol / Aliphatic acyclic compound / Alpha-hydroxy ketone / Hydrocarbon derivative / Ketone / Organic oxide / Secondary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
acetoin (CHEBI:15687)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ROWKJAVDOGWPAT-VKHMYHEASA-N
InChI
InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m0/s1
IUPAC Name
(3S)-3-hydroxybutan-2-one
SMILES
C[C@H](O)C(C)=O

References

General References
Not Available
KEGG Compound
C01769
PubChem Compound
447765
PubChem Substance
46504833
ChemSpider
394765
ChEBI
15687
ZINC
ZINC000000895238
PDBe Ligand
HBS
PDB Entries
1p28 / 6xew

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)15 °CPhysProp
boiling point (°C)143 °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility473.0 mg/mLALOGPS
logP-0.66ALOGPS
logP-0.14Chemaxon
logS0.73ALOGPS
pKa (Strongest Acidic)13.72Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity22.39 m3·mol-1Chemaxon
Polarizability9.06 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.9575
Caco-2 permeable+0.6005
P-glycoprotein substrateNon-substrate0.8252
P-glycoprotein inhibitor INon-inhibitor0.9372
P-glycoprotein inhibitor IINon-inhibitor0.9242
Renal organic cation transporterNon-inhibitor0.9391
CYP450 2C9 substrateNon-substrate0.8187
CYP450 2D6 substrateNon-substrate0.9237
CYP450 3A4 substrateNon-substrate0.7256
CYP450 1A2 substrateNon-inhibitor0.9059
CYP450 2C9 inhibitorNon-inhibitor0.9552
CYP450 2D6 inhibitorNon-inhibitor0.9467
CYP450 2C19 inhibitorNon-inhibitor0.9377
CYP450 3A4 inhibitorNon-inhibitor0.9561
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9656
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.6782
BiodegradationReady biodegradable0.8798
Rat acute toxicity1.2776 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9843
hERG inhibition (predictor II)Non-inhibitor0.9612
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9000000000-15ed087808debd745ef9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6t-9000000000-191d50e50fa3f6bb7356
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-ea809b2ff6bfe0f305fe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-5b3e4dfe3751a33772e4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-13cb1fd0221ed0467cb5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6t-9000000000-9c111aa26983ce710860
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fr7-9000000000-918b65006ea8a0f96959
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-110.2458425
predicted
DarkChem Lite v0.1.0
[M-H]-120.07361
predicted
DeepCCS 1.0 (2019)
[M+H]+111.1937425
predicted
DarkChem Lite v0.1.0
[M+H]+121.96902
predicted
DeepCCS 1.0 (2019)
[M+Na]+110.4921425
predicted
DarkChem Lite v0.1.0
[M+Na]+130.19176
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52