NAV

Ricinoleic acid

Identification

Generic Name
Ricinoleic acid
DrugBank Accession Number
DB02955
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCannabinoid receptor 1Not AvailableHumans
UCannabinoid receptor 2Not AvailableHumans
UTransient receptor potential cation channel subfamily V member 1Not AvailableHumans
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
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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
KEGG Compound
C08365
PubChem Compound
643684
PubChem Substance
46506721
ChemSpider
558800
RxNav
35605
ChEBI
28592
ChEMBL
CHEMBL3186422
ZINC
ZINC000012954494
PDBe Ligand
RCL
Wikipedia
Ricinoleic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability37.83 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/MSsplash10-03e9-2290000000-ba0115e2119c12c3267c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-6f679aeabdaa1a020656
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0490000000-32e6b06040a8893a1791
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01wr-5930000000-122b36b0bdd5a1688801
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-8890000000-9950a26f7a4400d2e5f3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-059y-9500000000-8f006c1ba4213570f9f4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.9462159
predicted
DarkChem Lite v0.1.0
[M-H]-208.2126159
predicted
DarkChem Lite v0.1.0
[M-H]-202.6522159
predicted
DarkChem Lite v0.1.0
[M-H]-181.82918
predicted
DeepCCS 1.0 (2019)
[M+H]+205.8481159
predicted
DarkChem Lite v0.1.0
[M+H]+208.7186159
predicted
DarkChem Lite v0.1.0
[M+H]+203.0298159
predicted
DarkChem Lite v0.1.0
[M+H]+184.3795
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.9271159
predicted
DarkChem Lite v0.1.0
[M+Na]+207.6316159
predicted
DarkChem Lite v0.1.0
[M+Na]+202.0143159
predicted
DarkChem Lite v0.1.0
[M+Na]+192.4605
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cannabinoid receptor 1
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
  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. [Article]
Details2. Cannabinoid receptor 2
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
  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. [Article]
Details3. Transient receptor potential cation channel subfamily V member 1
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
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at April 21, 2021 06:20