Identification
- Generic Name
- Caprylic acid
- DrugBank Accession Number
- DB04519
- Background
Caprylic acid is an eight-carbon chain fatty acid, also known systematically as 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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Caprylic acid (DB04519)
- Weight
- Average: 144.2114
Monoisotopic: 144.115029756 - Chemical Formula
- C8H16O2
- Synonyms
- 1-heptanecarboxylic acid
- Acide octanoïque
- Acide octanoique
- ácido octanoico
- Acidum octanocium
- Acidum octanoicum
- C8:0
- Caprylic acid
- Kaprylsäure
- n-caprylic acid
- n-octanoic acid
- n-Octoic acid
- n-octylic acid
- Octanoic acid
- Octoic acid
- Octylic acid
- External IDs
- EDENOR C 8-98-100
- FEMA NO. 2799
- NSC-5024
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPeroxisome proliferator-activated receptor alpha Not Available Humans U3-oxoacyl-[acyl-carrier-protein] synthase 1 Not Available Escherichia coli (strain K12) UAcyl-CoA thioesterase I Not Available Escherichia coli (strain K12) - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral rat LD50: 10080 mg/kg. Intravenous mouse LD50: 600 mg/kg. Skin rabbit LD50: over 5000 mg/kg.
- Pathways
Pathway Category Fatty Acid Biosynthesis Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcamprosate The excretion of Acamprosate can be decreased when combined with Caprylic acid. Acyclovir The excretion of Acyclovir can be decreased when combined with Caprylic acid. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Caprylic acid. Allopurinol The excretion of Allopurinol can be decreased when combined with Caprylic acid. Aminohippuric acid The excretion of Aminohippuric acid can be decreased when combined with Caprylic acid. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Medium-chain fatty acids
- Alternative Parents
- Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Medium-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- medium-chain fatty acid, straight-chain saturated fatty acid (CHEBI:28837) / Straight chain fatty acids, Saturated fatty acids (C06423) / Straight chain fatty acids (LMFA01010008)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- OBL58JN025
- CAS number
- 124-07-2
- InChI Key
- WWZKQHOCKIZLMA-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
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000482
- KEGG Drug
- D05220
- KEGG Compound
- C06423
- PubChem Compound
- 379
- PubChem Substance
- 46507647
- ChemSpider
- 370
- BindingDB
- 50485608
- 20178
- ChEBI
- 28837
- ChEMBL
- CHEMBL324846
- ZINC
- ZINC000001530416
- PDBe Ligand
- OCA
- Wikipedia
- Caprylic_acid
- PDB Entries
- 1h2b / 1u8u / 1v2g / 2bui / 2eum / 2qhs / 2wg9 / 3l91 / 3wl8 / 4rw3 … show 35 more
- MSDS
- Download (78.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Terminated Treatment Previously treated Myelodysplastic Syndromes (MDS) 1 1 Completed Treatment Essential Tremor 1 1, 2 Completed Treatment Essential Tremor 1 1, 2 Completed Treatment Essential Tremor of Voice / Essential Voice Tremor / Laryngeal tremor 1
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 (°C) 16.3 °C PhysProp boiling point (°C) 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 0.907 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 40.28 m3·mol-1 Chemaxon Polarizability 17.4 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8808 CYP450 2D6 inhibitor Non-inhibitor 0.9554 CYP450 2C19 inhibitor Non-inhibitor 0.9578 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (8.7 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.6913161 predictedDarkChem Lite v0.1.0 [M-H]- 137.7053161 predictedDarkChem Lite v0.1.0 [M-H]- 137.6357161 predictedDarkChem Lite v0.1.0 [M-H]- 142.15373 predictedDeepCCS 1.0 (2019) [M+H]+ 145.10825 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.74164 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
- Gene Name
- PPARA
- Uniprot ID
- Q07869
- Uniprot Name
- Peroxisome proliferator-activated receptor alpha
- Molecular Weight
- 52224.595 Da
References
- Vanden Heuvel JP, Thompson JT, Frame SR, Gillies PJ: Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci. 2006 Aug;92(2):476-89. Epub 2006 May 26. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- 3-oxoacyl-[acyl-carrier-protein] synthase activity
- Specific Function
- 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...
- Gene Name
- fabB
- Uniprot ID
- P0A953
- Uniprot Name
- 3-oxoacyl-[acyl-carrier-protein] synthase 1
- Molecular Weight
- 42612.995 Da
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Phospholipase activity
- Specific Function
- Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin.
- Gene Name
- tesA
- Uniprot ID
- P0ADA1
- Uniprot Name
- Acyl-CoA thioesterase I
- Molecular Weight
- 23621.955 Da
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- 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, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 07, 2021 03:11