NAV

4-hydroxybutan-2-one

Identification

Generic Name
4-hydroxybutan-2-one
DrugBank Accession Number
DB04094
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 88.1051
Monoisotopic: 88.0524295
Chemical Formula
C4H8O2
Synonyms
  • 3-Oxo-1-butanol
  • 3-Oxobutanol
  • 4-Hydroxy-2-butanone
  • Methylolacetone
  • Monomethylolacetone

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeptidyl-prolyl cis-trans isomerase FKBP1ANot AvailableHumans
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
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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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-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
Beta-hydroxy ketones
Alternative Parents
Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic acyclic compound / Beta-hydroxy ketone / Hydrocarbon derivative / Organic oxide / Primary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
methyl ketone, beta-hydroxy ketone (CHEBI:41268)
Affected organisms
Not Available

Chemical Identifiers

UNII
TCM0BJ44MF
CAS number
590-90-9
InChI Key
LVSQXDHWDCMMRJ-UHFFFAOYSA-N
InChI
InChI=1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3
IUPAC Name
4-hydroxybutan-2-one
SMILES
CC(=O)CCO

References

Synthesis Reference

Akinobu Matsuyama, Teruyuki Nikaido, Yoshinori Kobayashi, "Production of optically active 1,3-butanediol by asymmetric assimilation or reduction of 4-hydroxy-2-butanone." U.S. Patent US5219757, issued March, 1990.

US5219757
General References
Not Available
PubChem Compound
111509
PubChem Substance
46508666
ChemSpider
100056
ChEBI
41268
ZINC
ZINC000001672523
PDBe Ligand
BUQ
PDB Entries
1d7j

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility632.0 mg/mLALOGPS
logP-0.85ALOGPS
logP-0.47Chemaxon
logS0.86ALOGPS
pKa (Strongest Acidic)15.82Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity22.6 m3·mol-1Chemaxon
Polarizability9.21 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9975
Blood Brain Barrier+0.9763
Caco-2 permeable+0.7265
P-glycoprotein substrateNon-substrate0.73
P-glycoprotein inhibitor INon-inhibitor0.8949
P-glycoprotein inhibitor IINon-inhibitor0.8834
Renal organic cation transporterNon-inhibitor0.8691
CYP450 2C9 substrateNon-substrate0.7797
CYP450 2D6 substrateNon-substrate0.87
CYP450 3A4 substrateNon-substrate0.7135
CYP450 1A2 substrateNon-inhibitor0.5785
CYP450 2C9 inhibitorNon-inhibitor0.9565
CYP450 2D6 inhibitorNon-inhibitor0.941
CYP450 2C19 inhibitorNon-inhibitor0.8862
CYP450 3A4 inhibitorNon-inhibitor0.9621
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9657
Ames testNon AMES toxic0.9128
CarcinogenicityNon-carcinogens0.5113
BiodegradationReady biodegradable0.9872
Rat acute toxicity1.2721 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9089
hERG inhibition (predictor II)Non-inhibitor0.9411
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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-7280da5a63dca61cb6f6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Peptidyl-prolyl cis-trans isomerase FKBP1A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Type i transforming growth factor beta receptor binding
Specific Function
Keeps in an inactive conformation TGFBR1, the TGF-beta type I serine/threonine kinase receptor, preventing TGF-beta receptor activation in absence of ligand. Recruites SMAD7 to ACVR1B which prevent...
Gene Name
FKBP1A
Uniprot ID
P62942
Uniprot Name
Peptidyl-prolyl cis-trans isomerase FKBP1A
Molecular Weight
11950.665 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

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