Butyric Acid

Targets (3)Enzymes (1)

Identification

Name
Butyric Acid
Accession Number
DB03568  (EXPT00774)
Type
Small Molecule
Groups
Experimental, Investigational
Description

A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.

Structure
Thumb
3D
Similar Structures
Synonyms
  • 1-propanecarboxylic acid
  • Butanoic acid
  • Butyrate
  • Butyricum acidum
  • Ethylacetic acid
  • N-butanoic acid
  • N-butyric acid
  • Propylformic acid
External IDs
FEMA NO. 2221 / NSC-8415
Categories
UNII
40UIR9Q29H
CAS number
107-92-6
Weight
Average: 88.1051
Monoisotopic: 88.0524295
Chemical Formula
C4H8O2
InChI Key
FERIUCNNQQJTOY-UHFFFAOYSA-N
InChI
InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
IUPAC Name
butanoic acid
SMILES
CCCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCholinesteraseNot AvailableHumans
U2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolaseNot AvailablePseudomonas fluorescens
U(S)-2-haloacid dehalogenaseNot AvailablePseudomonas sp. (strain YL)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Butyrate MetabolismMetabolic
Fatty Acid Biosynthesis Metabolic
Fatty Acid BiosynthesisMetabolic
Fatty Acid Oxidation (Butanoate)Metabolic
Butyrate MetabolismMetabolic
Fatty Acid BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Haruhiko Kikuchi, "Process for preparing 4-(4-biphenylyl)-4-oxo-butanoic acid." U.S. Patent US4621154, issued November, 1977.

US4621154
General References
Not Available
External Links
Human Metabolome Database
HMDB0000039
KEGG Compound
C00246
PubChem Compound
264
PubChem Substance
46505927
ChemSpider
259
BindingDB
26109
ChEBI
30772
ChEMBL
CHEMBL14227
IUPHAR
1059
Guide to Pharmacology
GtP Drug Page
HET
BUA
Wikipedia
Butyric_acid
PDB Entries
1p0i / 1ugp / 1uk7 / 1zrm / 2cz0 / 2cz1 / 2ha7 / 2j4c / 3dlt / 3i3f …
show 9 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAtaxia Telangiectasia (AT)1
Not AvailableCompletedBasic ScienceVisceral (Hyper)Sensitivity1

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)-5.7 °CPhysProp
boiling point (°C)163.7 °CPhysProp
water solubility6E+004 mg/L (at 25 °C)HEMPHILL,L & SWANSON,WS (1964)
logP0.79HANSCH,C ET AL. (1995)
logS-0.19ADME Research, USCD
pKa4.82 (at 25 °C)RIDDICK,JA ET AL. (1986)
Predicted Properties
PropertyValueSource
Water Solubility239.0 mg/mLALOGPS
logP0.78ALOGPS
logP0.92ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.87 m3·mol-1ChemAxon
Polarizability9.22 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9938
Blood Brain Barrier+0.9572
Caco-2 permeable+0.7456
P-glycoprotein substrateNon-substrate0.759
P-glycoprotein inhibitor INon-inhibitor0.9554
P-glycoprotein inhibitor IINon-inhibitor0.9773
Renal organic cation transporterNon-inhibitor0.9544
CYP450 2C9 substrateNon-substrate0.8026
CYP450 2D6 substrateNon-substrate0.9177
CYP450 3A4 substrateNon-substrate0.7582
CYP450 1A2 substrateInhibitor0.5106
CYP450 2C9 inhibitorNon-inhibitor0.9345
CYP450 2D6 inhibitorNon-inhibitor0.9519
CYP450 2C19 inhibitorNon-inhibitor0.9613
CYP450 3A4 inhibitorNon-inhibitor0.972
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9849
Ames testNon AMES toxic0.95
CarcinogenicityNon-carcinogens0.5611
BiodegradationReady biodegradable0.9659
Rat acute toxicity1.6755 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9484
hERG inhibition (predictor II)Non-inhibitor0.9677
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-MSsplash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1
GC-MS Spectrum - EI-BGC-MSsplash10-03dl-9000000000-032fc35b394786b5896a
Mass Spectrum (Electron Ionization)MSsplash10-03di-9000000000-5338ff8a9c4e59150aba
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000i-9000000000-7f461db56bfd8568ec71
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-000i-9000000000-66f857fa612f773837bc
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-000i-9000000000-e6689b2e6bf21570b934
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-03dl-9000000000-b2ffa7d67b2466dea94f
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-03dl-9000000000-7467bf19c64fd3f51105
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-9000000000-9ae015043b014b3c93d9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000i-9000000000-e30b3c6bd6218b9b49e1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-000i-9000000000-efbb0e35a19a1713240b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-acb5cf0017a9ee680dd8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-9000000000-812e24462a71dccb0fec
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-f9d30338ca1ee9409964
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-9d749b6b6cf2f93a8f85
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ku-9000000000-ee742730266fb4997777
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-88fc445cddcb726e93d8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-9ae015043b014b3c93d9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-e30b3c6bd6218b9b49e1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-efbb0e35a19a1713240b
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Straight chain fatty acids
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Straight chain fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
straight-chain saturated fatty acid, short-chain fatty acid (CHEBI:30772) / Straight chain fatty acids, Saturated fatty acids (C00246) / Straight chain fatty acids (LMFA01010004)

Targets

Details1. Cholinesterase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
Details2. 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Hydrolase activity
Specific Function
Not Available
Gene Name
cumD
Uniprot ID
P96965
Uniprot Name
2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase
Molecular Weight
31489.385 Da
Details3. (S)-2-haloacid dehalogenase
Kind
Protein
Organism
Pseudomonas sp. (strain YL)
Pharmacological action
Unknown
General Function
(s)-2-haloacid dehalogenase activity
Specific Function
Catalyzes the hydrolytic dehalogenation of small (S)-2-haloalkanoic acids to yield the corresponding (R)-2-hydroxyalkanoic acids. Acts on acids of short chain lengths, C(2) to C(4), with inversion ...
Gene Name
Not Available
Uniprot ID
Q53464
Uniprot Name
(S)-2-haloacid dehalogenase
Molecular Weight
26176.335 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. [PubMed:17139284]
  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. [PubMed:17016423]

Enzymes

Details1. Cholinesterase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:37