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Identification
NameButenoic Acid
Accession NumberDB02074  (EXPT00670)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
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
CategoriesNot Available
UNIIYW5WZZ4O5Q
CAS number107-93-7
WeightAverage: 86.0892
Monoisotopic: 86.036779436
Chemical FormulaC4H6O2
InChI KeyInChIKey=LDHQCZJRKDOVOX-NSCUHMNNSA-N
InChI
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
IUPAC Name
(2E)-but-2-enoic acid
SMILES
C\C=C\C(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
  • Unsaturated fatty acid
  • 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
Fatty Acid BiosynthesisMetabolicSMP00456
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9923
Blood Brain Barrier+0.9624
Caco-2 permeable+0.6066
P-glycoprotein substrateNon-substrate0.8364
P-glycoprotein inhibitor INon-inhibitor0.9822
P-glycoprotein inhibitor IINon-inhibitor0.9849
Renal organic cation transporterNon-inhibitor0.9473
CYP450 2C9 substrateNon-substrate0.7332
CYP450 2D6 substrateNon-substrate0.9515
CYP450 3A4 substrateNon-substrate0.7887
CYP450 1A2 substrateNon-inhibitor0.9227
CYP450 2C9 inhibitorNon-inhibitor0.9526
CYP450 2D6 inhibitorNon-inhibitor0.9707
CYP450 2C19 inhibitorNon-inhibitor0.9816
CYP450 3A4 inhibitorNon-inhibitor0.9748
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9839
Ames testNon AMES toxic0.9133
CarcinogenicityCarcinogens 0.6536
BiodegradationReady biodegradable0.8123
Rat acute toxicity1.9038 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.97
hERG inhibition (predictor II)Non-inhibitor0.9893
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 point72 °CPhysProp
boiling point184.7 °CPhysProp
water solubility9.4E+004 mg/L (at 25 °C)RIDDICK,JA ET AL. (1986)
pKa4.17 (at 18 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility101.0 mg/mLALOGPS
logP0.94ALOGPS
logP0.92ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.96 m3·mol-1ChemAxon
Polarizability8.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Wolfgang Krause, Hansgeorg Ernst, Joachim Paust, Udo Rheude, Walter Dobler, “Preparation of alkylesters of 0,0-dialkyl-4-phosphono-2-methyl-2-butenoic acid and alkyl esters of 4-halo-2-methyl-2-butenoic acid containing a high percentage of E isomers.” U.S. Patent US5717128, issued November, 1971.

US5717128
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phospholipid binding
Specific Function:
Plays a role in lipoprotein-mediated cholesterol uptake in hepatocytes (PubMed:25732850). Binds cholesterol (PubMed:25732850). Binds free fatty acids and their coenzyme A derivatives, bilirubin, and some other small molecules in the cytoplasm. May be involved in intracellular lipid transport (By similarity).
Gene Name:
FABP1
Uniprot ID:
P07148
Molecular Weight:
14208.34 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 ]
  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. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17