Identification
- Generic Name
- Ricinoleic acid
- DrugBank Accession Number
- DB02955
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Ricinoleic acid (DB02955)
- Weight
- Average: 298.467
Monoisotopic: 298.250794955 - Chemical Formula
- C18H34O3
- Synonyms
- (cis,R)-12-hydroxyoctadec-9-enoic acid
- (Z,R)-12-hydroxyoctadec-9-enoic acid
- 12-Hydroxy-9-octadecenoic acid
- 12-Hydroxy-cis-9-octadecenoic acid
- 12-hydroxyoleic acid
- Ricinoleic acid
- Ricinolic acid
- Ricinolsäure
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.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCannabinoid receptor 1 Not Available Humans UCannabinoid receptor 2 Not Available Humans UTransient receptor potential cation channel subfamily V member 1 Not Available Humans - 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.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Long-chain fatty acids
- Alternative Parents
- Hydroxy fatty acids / Unsaturated fatty acids / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxy fatty acid / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- (9Z)-12-hydroxyoctadec-9-enoic acid (CHEBI:28592) / Unsaturated fatty acids, Hydroxy fatty acids (C08365) / Other Octadecanoids (LMFA02000184)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- I2D0F69854
- CAS number
- 141-22-0
- InChI Key
- WBHHMMIMDMUBKC-QJWNTBNXSA-N
- InChI
- InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1
- IUPAC Name
- (9Z,12R)-12-hydroxyoctadec-9-enoic acid
- SMILES
- CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O
References
- Synthesis Reference
Bernd Fabry, Robert Piorr, Frank Clasen, Horst Ritterbex, Hans Bornmann, "Process for the preparation of reaction products of epoxidized ricinoleic acid glycerides with sulfur trioxide." U.S. Patent US4981617, issued December, 1966.
US4981617- General References
- Not Available
- External Links
- KEGG Compound
- C08365
- PubChem Compound
- 643684
- PubChem Substance
- 46506721
- ChemSpider
- 558800
- 35605
- ChEBI
- 28592
- ChEMBL
- CHEMBL3186422
- ZINC
- ZINC000012954494
- PDBe Ligand
- RCL
- Wikipedia
- Ricinoleic_acid
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Dispensing Solutions
- Hope Pharmaceuticals
- Pharmedix
- Physicians Total Care Inc.
- Qualitest
- Truett Laboratories
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 5.5 °C PhysProp boiling point (°C) 245 °C PhysProp water solubility 3460 mg/L (at 25 °C) SEIDELL,A (1941) - Predicted Properties
Property Value Source Water Solubility 0.00254 mg/mL ALOGPS logP 6.14 ALOGPS logP 5.4 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 4.99 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 89.07 m3·mol-1 Chemaxon Polarizability 37.83 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9935 Blood Brain Barrier + 0.8153 Caco-2 permeable + 0.7403 P-glycoprotein substrate Substrate 0.526 P-glycoprotein inhibitor I Non-inhibitor 0.958 P-glycoprotein inhibitor II Non-inhibitor 0.7879 Renal organic cation transporter Non-inhibitor 0.9265 CYP450 2C9 substrate Non-substrate 0.8011 CYP450 2D6 substrate Non-substrate 0.8869 CYP450 3A4 substrate Non-substrate 0.6359 CYP450 1A2 substrate Inhibitor 0.704 CYP450 2C9 inhibitor Non-inhibitor 0.9132 CYP450 2D6 inhibitor Non-inhibitor 0.9424 CYP450 2C19 inhibitor Non-inhibitor 0.9359 CYP450 3A4 inhibitor Non-inhibitor 0.9015 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8944 Ames test Non AMES toxic 0.9701 Carcinogenicity Non-carcinogens 0.7204 Biodegradation Ready biodegradable 0.8471 Rat acute toxicity 1.5862 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9332 hERG inhibition (predictor II) Non-inhibitor 0.8619
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Drug binding
- Specific Function
- Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered l...
- Gene Name
- CNR1
- Uniprot ID
- P21554
- Uniprot Name
- Cannabinoid receptor 1
- Molecular Weight
- 52857.365 Da
References
- Appendino G, Cascio MG, Bacchiega S, Moriello AS, Minassi A, Thomas A, Ross R, Pertwee R, De Petrocellis L, Di Marzo V: First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB2 receptors and non-polyunsaturated fatty acid-derived CB2-selective ligands. FEBS Lett. 2006 Jan 23;580(2):568-74. Epub 2005 Dec 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cannabinoid receptor activity
- Specific Function
- Heterotrimeric G protein-coupled receptor for endocannabinoid 2-arachidonoylglycerol mediating inhibition of adenylate cyclase. May function in inflammatory response, nociceptive transmission and b...
- Gene Name
- CNR2
- Uniprot ID
- P34972
- Uniprot Name
- Cannabinoid receptor 2
- Molecular Weight
- 39680.275 Da
References
- Appendino G, Cascio MG, Bacchiega S, Moriello AS, Minassi A, Thomas A, Ross R, Pertwee R, De Petrocellis L, Di Marzo V: First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB2 receptors and non-polyunsaturated fatty acid-derived CB2-selective ligands. FEBS Lett. 2006 Jan 23;580(2):568-74. Epub 2005 Dec 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
- Gene Name
- TRPV1
- Uniprot ID
- Q8NER1
- Uniprot Name
- Transient receptor potential cation channel subfamily V member 1
- Molecular Weight
- 94955.33 Da
References
- Appendino G, Cascio MG, Bacchiega S, Moriello AS, Minassi A, Thomas A, Ross R, Pertwee R, De Petrocellis L, Di Marzo V: First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB2 receptors and non-polyunsaturated fatty acid-derived CB2-selective ligands. FEBS Lett. 2006 Jan 23;580(2):568-74. Epub 2005 Dec 29. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 21, 2021 06:20