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Identification
NameButanoic Acid
Accession NumberDB03568  (EXPT00774)
TypeSmall Molecule
GroupsExperimental
DescriptionA four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII40UIR9Q29H
CAS number107-92-6
WeightAverage: 88.1051
Monoisotopic: 88.0524295
Chemical FormulaC4H8O2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Butyrate MetabolismMetabolicSMP00073
Fatty Acid BiosynthesisMetabolicSMP00456
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point-5.7 °CPhysProp
boiling point163.7 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-7f461db56bfd8568ec71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000i-9000000000-66f857fa612f773837bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-e6689b2e6bf21570b934View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b2ffa7d67b2466dea94fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-7467bf19c64fd3f51105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-9ae015043b014b3c93d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-e30b3c6bd6218b9b49e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-efbb0e35a19a1713240bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-acb5cf0017a9ee680dd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-812e24462a71dccb0fecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f9d30338ca1ee9409964View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-9d749b6b6cf2f93a8f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-9000000000-ee742730266fb4997777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-88fc445cddcb726e93d8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-5338ff8a9c4e59150abaView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Butanoic Acid.
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Butanoic Acid.
AmphetamineAmphetamine may decrease the sedative activities of Butanoic Acid.
BenzphetamineBenzphetamine may decrease the sedative activities of Butanoic Acid.
Benzylpenicilloyl PolylysineButanoic Acid may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Butanoic Acid.
ChlorphentermineChlorphentermine may decrease the sedative activities of Butanoic Acid.
DextroamphetamineDextroamphetamine may decrease the sedative activities of Butanoic Acid.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Butanoic Acid.
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide may decrease the sedative activities of Butanoic Acid.
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Butanoic Acid.
MephentermineMephentermine may decrease the sedative activities of Butanoic Acid.
MethamphetamineMethamphetamine may decrease the sedative activities of Butanoic Acid.
PhenterminePhentermine may decrease the sedative activities of Butanoic Acid.
Food InteractionsNot Available

Targets

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 of configuration at C-2.
Gene Name:
Not Available
Uniprot ID:
Q53464
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 ]
Kind
Protein
Organism
Human
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
Molecular Weight:
68417.575 Da
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
unknown
General Function:
Hydrolase activity
Specific Function:
Not Available
Gene Name:
cumD
Uniprot ID:
P96965
Molecular Weight:
31489.385 Da

Enzymes

Kind
Protein
Organism
Human
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
Molecular Weight:
68417.575 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23