Ricinoleic Acid

Identification

Name
Ricinoleic Acid
Accession Number
DB02955  (EXPT02762)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
I2D0F69854
CAS number
141-22-0
Weight
Average: 298.467
Monoisotopic: 298.250794955
Chemical Formula
C18H34O3
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
[H]\C(CCCCCCCC(O)=O)=C(/[H])C[C@]([H])(O)CCCCCC

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCannabinoid receptor 1Not AvailableHuman
UCannabinoid receptor 2Not AvailableHuman
UTransient receptor potential cation channel subfamily V member 1Not AvailableHuman
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
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
ChEBI
28592
ChEMBL
CHEMBL3186422
HET
RCL

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
melting point (°C)5.5 °CPhysProp
boiling point (°C)245 °CPhysProp
water solubility3460 mg/L (at 25 °C)SEIDELL,A (1941)
Predicted Properties
PropertyValueSource
Water Solubility0.00254 mg/mLALOGPS
logP6.14ALOGPS
logP5.4ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity89.07 m3·mol-1ChemAxon
Polarizability37.85 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.8153
Caco-2 permeable+0.7403
P-glycoprotein substrateSubstrate0.526
P-glycoprotein inhibitor INon-inhibitor0.958
P-glycoprotein inhibitor IINon-inhibitor0.7879
Renal organic cation transporterNon-inhibitor0.9265
CYP450 2C9 substrateNon-substrate0.8011
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateNon-substrate0.6359
CYP450 1A2 substrateInhibitor0.704
CYP450 2C9 inhibitorNon-inhibitor0.9132
CYP450 2D6 inhibitorNon-inhibitor0.9424
CYP450 2C19 inhibitorNon-inhibitor0.9359
CYP450 3A4 inhibitorNon-inhibitor0.9015
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8944
Ames testNon AMES toxic0.9701
CarcinogenicityNon-carcinogens0.7204
BiodegradationReady biodegradable0.8471
Rat acute toxicity1.5862 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9332
hERG inhibition (predictor II)Non-inhibitor0.8619
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Long-chain fatty acid / Hydroxy fatty acid / Unsaturated fatty acid / Secondary alcohol / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
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)

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:16406364]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:16406364]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:16406364]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:26