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targets (2) transporters (3)
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Identification
Name Caprylic acid
Accession Number DB04519 (EXPT02413)
Type small molecule
Groups experimental
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
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Display: 2D Structure | 3D Structure
Synonyms
capryloate
Caprylsaeure
Enantic acid
Kaprylsaeure
n-caprylic acid
n-octanoic acid
n-Octoic acid
n-octylic acid
neo-fat 8
octanoate
octanoic acid
Octic acid
octoic acid
Octylic acid
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Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories Not Available
CAS number 124-07-2
Weight Average: 144.2114
Monoisotopic: 144.115029756
Chemical Formula C8H16O2
InChI Key InChIKey=WWZKQHOCKIZLMA-UHFFFAOYSA-N
InChI
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
Plain Text
IUPAC Name
octanoic acid
SMILES
CCCCCCCC(O)=O
Plain Text
Mass Spec show (8.7 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
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 Oral rat LD50: 10080 mg/kg. Intravenous mouse LD50: 600 mg/kg. Skin rabbit LD50: over 5000 mg/kg.
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point 16.3 °C PhysProp
boiling point 239 °C PhysProp
water solubility 789 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 3.05 HANSCH,C ET AL. (1995)
pKa 4.89 (at 25 °C) DEAN,JA (1987)
Predicted Properties
Property Value Source
water solubility 9.07e-01 g/l ALOGPS
logP 2.92 ALOGPS
logP 2.7 ChemAxon
logS -2.2 ALOGPS
pKa (strongest acidic) 5.19 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 37.3 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 40.28 ChemAxon
polarizability 17.4 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D05220 Link_out
KEGG Compound C06423 Link_out
PubChem Compound 379 Link_out
PubChem Substance 46507647 Link_out
ChEBI 28837 Link_out
ChEMBL 28837 Link_out
HET OCA Link_out
Wikipedia http://en.wikipedia.org/wiki/Caprylic_acid Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (78.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

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

Pharmacological action: unknown

Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Specific for elongation from C-10 to unsaturated C-16 and C-18 fatty acids

Organism class: bacterial
UniProt ID: P0A953 Link_out
Gene: fabB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

2. Acyl-CoA thioesterase I precursor

Pharmacological action: unknown

Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin

Organism class: bacterial
UniProt ID: P0ADA1 Link_out
Gene: tesA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

UniProt ID: Q8TCC7 Link_out
Gene: SLC22A8 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds

UniProt ID: Q9NSA0 Link_out
Gene: SLC22A11 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:23