NAV

2-Butanol

Identification

Generic Name
2-Butanol
DrugBank Accession Number
DB02606
Background

Not Available

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 74.1216
Monoisotopic: 74.073164942
Chemical Formula
C4H10O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNADP-dependent isopropanol dehydrogenaseNot AvailableThermoanaerobacter brockii
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 secondary alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Secondary alcohols
Alternative Parents
Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Hydrocarbon derivative / Secondary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
butan-2-ol (CHEBI:35686)
Affected organisms
Not Available

Chemical Identifiers

UNII
DLH38K423J
CAS number
78-92-2
InChI Key
BTANRVKWQNVYAZ-SCSAIBSYSA-N
InChI
InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3/t4-/m1/s1
IUPAC Name
(2R)-butan-2-ol
SMILES
CC[C@@H](C)O

References

Synthesis Reference

Udo Kraatz, Graham Holmwood, Dieter Berg, Manfred Plempel, "Process for the preparation of optically active azolyl-carbinol derivatives, optically active 2-(4chloro-phenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol, prepared by this process and its use as an antimycotic." U.S. Patent US4783538, issued February, 1982.

US4783538
General References
Not Available
PubChem Compound
84682
PubChem Substance
46507541
ChemSpider
76392
ChEBI
35686
ZINC
ZINC000001622055
PDBe Ligand
SBT
Wikipedia
2-Butanol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedNot AvailableHealthy Adults1

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)-114.7 °CPhysProp
boiling point (°C)99.5 °CPhysProp
water solubility1.81E+005 mg/L (at 25 °C)HEFTER,GT (1984A)
logP0.61HANSCH,C ET AL. (1995)
pKa17.6 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility195.0 mg/mLALOGPS
logP0.66ALOGPS
logP0.78Chemaxon
logS0.42ALOGPS
pKa (Strongest Acidic)17.69Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area20.23 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity21.95 m3·mol-1Chemaxon
Polarizability9.03 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9709
Caco-2 permeable+0.7523
P-glycoprotein substrateNon-substrate0.7566
P-glycoprotein inhibitor INon-inhibitor0.9019
P-glycoprotein inhibitor IINon-inhibitor0.9597
Renal organic cation transporterNon-inhibitor0.9548
CYP450 2C9 substrateNon-substrate0.8359
CYP450 2D6 substrateNon-substrate0.8827
CYP450 3A4 substrateNon-substrate0.7318
CYP450 1A2 substrateNon-inhibitor0.6803
CYP450 2C9 inhibitorNon-inhibitor0.9332
CYP450 2D6 inhibitorNon-inhibitor0.932
CYP450 2C19 inhibitorNon-inhibitor0.8283
CYP450 3A4 inhibitorNon-inhibitor0.967
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9343
Ames testNon AMES toxic0.8411
CarcinogenicityCarcinogens 0.7781
BiodegradationReady biodegradable0.8176
Rat acute toxicity1.5604 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9301
hERG inhibition (predictor II)Non-inhibitor0.9077
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-MSsplash10-056r-9000000000-36766522c997d22e8330
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-594c3647ce7e4e3b891b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-b35cef2eb710949d8f2d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-cb3e2813c433e06adc54
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-365a1cb3a70ac066a12b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-9000000000-331d99c07c6c0f2f29f7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052u-9000000000-6c2e250f3b8f1f3b7392
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]-119.178894
predicted
DeepCCS 1.0 (2019)
[M+H]+121.11439
predicted
DeepCCS 1.0 (2019)
[M+Na]+129.40448
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. NADP-dependent isopropanol dehydrogenase
Kind
Protein
Organism
Thermoanaerobacter brockii
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Alcohol dehydrogenase with a preference for medium chain secondary alcohols, such as 2-butanol and isopropanol. Has very low activity with primary alcohols, such as ethanol. Under physiological con...
Gene Name
adh
Uniprot ID
P14941
Uniprot Name
NADP-dependent isopropanol dehydrogenase
Molecular Weight
37646.685 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]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:44