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Identification
NameCaprylic acid
Accession NumberDB04519  (EXPT02413)
TypeSmall Molecule
GroupsExperimental
Description

Caprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid-like smell that is minimally soluble in water.

Structure
Thumb
Synonyms
SynonymLanguageCode
capryloateNot AvailableNot Available
CaprylsaeureNot AvailableNot Available
Enantic acidNot AvailableNot Available
KaprylsaeureNot AvailableNot Available
n-caprylic acidNot AvailableNot Available
n-octanoic acidNot AvailableNot Available
n-Octoic acidNot AvailableNot Available
n-octylic acidNot AvailableNot Available
neo-fat 8Not AvailableNot Available
octanoateNot AvailableNot Available
octanoic acidNot AvailableNot Available
Octic acidNot AvailableNot Available
octoic acidNot AvailableNot Available
Octylic acidNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number124-07-2
WeightAverage: 144.2114
Monoisotopic: 144.115029756
Chemical FormulaC8H16O2
InChI KeyWWZKQHOCKIZLMA-UHFFFAOYSA-N
InChI
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
IUPAC Name
octanoic acid
SMILES
CCCCCCCC(O)=O
Mass Specshow(8.7 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassFatty Acids and Conjugates
SubclassStraight Chain Fatty Acids
Direct parentStraight Chain Fatty Acids
Alternative parentsPolyamines; Enolates; Carboxylic Acids
Substituentsenolate; polyamine; carboxylic acid; carboxylic acid derivative
Classification descriptionThis compound belongs to the straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral rat LD50: 10080 mg/kg. Intravenous mouse LD50: 600 mg/kg. Skin rabbit LD50: over 5000 mg/kg.
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Fatty Acid BiosynthesisMetabolicSMP00456
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9888
Blood Brain Barrier + 0.9488
Caco-2 permeable + 0.8326
P-glycoprotein substrate Non-substrate 0.6321
P-glycoprotein inhibitor I Non-inhibitor 0.9598
P-glycoprotein inhibitor II Non-inhibitor 0.9277
Renal organic cation transporter Non-inhibitor 0.9266
CYP450 2C9 substrate Non-substrate 0.7886
CYP450 2D6 substrate Non-substrate 0.8956
CYP450 3A4 substrate Non-substrate 0.6982
CYP450 1A2 substrate Inhibitor 0.8326
CYP450 2C9 substrate Non-inhibitor 0.8808
CYP450 2D6 substrate Non-inhibitor 0.9554
CYP450 2C19 substrate Non-inhibitor 0.9578
CYP450 3A4 substrate Non-inhibitor 0.9484
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9647
Ames test Non AMES toxic 0.9865
Carcinogenicity Non-carcinogens 0.6452
Biodegradation Ready biodegradable 0.8795
Rat acute toxicity 1.3275 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9322
hERG inhibition (predictor II) Non-inhibitor 0.8868
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point16.3 °CPhysProp
boiling point239 °CPhysProp
water solubility789 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.05HANSCH,C ET AL. (1995)
pKa4.89 (at 25 °C)DEAN,JA (1987)
Predicted Properties
PropertyValueSource
Water Solubility0.907ALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m3·mol-1ChemAxon
Polarizability17.4 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

William Elliott Bay, Joseph Norman Bernadino, George Frederick Klein, Yi Ren, Pingsheng Zhang, “METHODS FOR PRODUCING N-(8-[2-HYDROXYBENZOYL]-AMINO) CAPRYLIC ACID.” U.S. Patent US20080064890, issued March 13, 2008.

US20080064890
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD05220
KEGG CompoundC06423
PubChem Compound379
PubChem Substance46507647
ChEBI28837
ChEMBL
HETOCA
WikipediaCaprylic_acid
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(78.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 3-oxoacyl-[acyl-carrier-protein] synthase 1

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
3-oxoacyl-[acyl-carrier-protein] synthase 1 P0A953 Details

2. Acyl-CoA thioesterase I

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Acyl-CoA thioesterase I P0ADA1 Details

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. Pubmed
  2. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. Pubmed

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. Pubmed

3. Solute carrier family 22 member 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

References:

  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:25